Structure SMILES Reaxys Registry Number Link to Reaxys Px CAS

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Reaxys Substance Link to CAS Registry Molecular Molecula Lipinski Veber Target Bioassay Measured Qualitativ Quantitat Structure SMILES Registry pX Chemical Name InChI Key LogP Target Name Action on Unit Reaxys Number Formula r Weight Number Number Species Details Parameter e value ive value Number Target

N-((S)-1-((S)-1-formyl-2- CC(C)C[C@H](NC(=O)C1 ((S)-2-oxopyrrolidin-3- Sars Cov 3C-Like =CC2=CC=CC=C2N1)C(= Coronavir 1.3E+07 1.3E+07 10.7 yl)ethylcarbamoyl)-3- C22H28N4O4 412.489 HXJZYYCILNIXEI-BQFCYCMXSA-N2.331 4 1 Protease Inhibitor Inhibitory activityIC50 againstnM SARS-CoV= 3C-like protease catalyzed0.02 cleavage of TAMRA- SITSAVLQSGFRKMK-(DABCYL)-OH to TAMRA - SITSAVLQ and SGFRKMK- (DABCYL)-OH using 4.0 uM FRET substrate with the compound dissolved in 4 DMSO, pH 7.0 (HEPES buffer) O)N[C@@H](C[C@@H] idae 1CCNC1=O)C=O methylbutyl)-1H-indole-2- [Coronaviridae] carboxamide

CC(C)C[C@H](NC(=O)[C N-[(benzyloxy)carbonyl]-L- Sars Cov 3C-Like @@H](NC(=O)OCC1=CC valyl-N1-{1-formyl-2-[(3S)- Coronavir =CC=C1)C(C)C)C(=O)NC( 1.5E+07 1.5E+07 10.2 C26H38N4O6 502.611 RUHYGYHBVKWREW-UZVDJONISA-N2.682 3 0 Protease Inhibitor Inhibitory activityIC50 againstnM SARS-CoV= 3C-like protease catalyzed0.06 cleavage of TAMRA- SITSAVLQSGFRKMK-(DABCYL)-OH to TAMRA - SITSAVLQ and SGFRKMK- (DABCYL)-OH using 4.0 uM FRET substrate with the compound dissolved in 4 DMSO, pH 7.0 (HEPES buffer) 2-oxopyrrolidin-3-yl]ethyl}- idae C[C@@H]1CCNC1=O)C= [Coronaviridae] O L-leucinamide

CC[C@H](C)[C@H](NC(= O)[C@H](CO)NC(=O)[C @H](CCCCN)NC(=O)[C@ H](CCC(N)=O)NC(=O)[C @H](CO)NC(=O)[C@@H Spike SARS ](NC(=O)[C@@H](N)CO) glycoprotein [C@@H](C)O)C(=O)N[C 2.5E+07 2.5E+07 8.73 C56H94N14O20S1315.51 RBLTWUZIFRZOSV-SQWMWQRLSA-N-8.375 1 0 coronavir Inhibitor ConcentrationIC50 required fornM inhibition= of SARS CoV Spike1.88 protein binding to Angiotensin converting enzyme 2 [SARS @@H](C(C)C)C(=O)N[C us @@H](C)C(=O)N[C@@ coronavirus] H](CC1=CC=C(O)C=C1)C( =O)N[C@@H]([C@@H]( C)O)C(=O)N[C@@H](CC SC)C(O)=O

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS (=CC=C1)N(C)C)C(C)C)C( product of 2.3E+07 2.3E+07 8.52 1417704-35-8 C35H46N6O6S678.853 CALSXGHSUKIJHM-GCIMQLSOSA-N3.516 2 0 coronavir Ki (inhibitionmuM constant) 0.003 =O)N[C@@H](C[C@@H Replicase ]1CCNC1=O)C(=O)C1=N us C2=CC=CC=C2S1 polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)OCC1=CC SARS =CC=C1)C(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 8.39 1359941-93-7 C33H41N5O6S635.784 KSCRVOKQPYZBHZ-IXPOFIJOSA-N3.789 2 0 coronavir Ki (inhibitionmuM constant) 0.0041 @@H](C[C@@H]1CCNC Replicase 1=O)C(=O)C1=NC2=CC= us CC=C2S1 polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS =C(O)C=C1)C(C)C)C(=O) product of 2.3E+07 2.3E+07 7.96 1359941-94-8 C33H41N5O7S651.784 ORLPJQUZUWTHRB-QIBSBUDHSA-N2.901 3 0 coronavir Ki (inhibitionmuM constant) 0.011 N[C@@H](C[C@@H]1C Replicase CNC1=O)C(=O)C1=NC2= us CC=CC=C2S1 polyprotein 1ab) [SARS coronavirus]

3C-like proteinase COC1=CC=C(OCC(=O)N[ (cleavage C@@H](C(C)C)C(=O)N[C SARS @@H](CC(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 7.85 1383922-80-2 C34H43N5O7S665.811 DYFSDLMESFFYEO-KXDOSHFCSA-N3.222 3 0 coronavir Ki (inhibitionmuM constant) 0.014 @@H](C[C@@H]2CCNC Replicase 2=O)C(=O)C2=NC3=CC= us CC=C3S2)C=C1 polyprotein 1ab) [SARS coronavirus]

sodium (2S)-2-((S)-2- (((benzyloxy)carbonyl)ami [Na+].CC(C)C[C@H](NC( no)-4-methylpentanamido)- 3C-like protease Coronavir =O)OCC1=CC=CC=C1)C( 2.3E+07 2.3E+07 7.7 1416992-39-6 C21H30N3O8S*Na507.54 BSPJDKCMFIPBAW-JPBGFCRCSA-M0.325 2 0 Inhibitor EC50 muM 0.02 - 0.05 =O)N[C@@H](CC1CCNC 1-hydroxy-3-(2- [Coronavirinae] inae 1=O)C(O)S([O-])(=O)=O oxopyrrolidin-3-yl)propane- 1-sulfonate

3C-like proteinase (cleavage OB(O)C1=CC(=CC(=C1)N SARS (=O)=O)C(=O)NC1=CC=C product of 1.9E+07 1.9E+07 7.66 693235-40-4 C20H16B2N4O10493.99 JBHJLTFEEOIBFO-UHFFFAOYSA-N1.798 3 1 coronavir Ki (inhibitionmuM constant) 0.022 (NC(=O)C2=CC(=CC(=C2) Replicase B(O)O)N(=O)=O)C=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS =CC=C1)C(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 7.66 1383922-52-8 C33H41N5O6S635.784 APIXGBAHHCHXMO-WWZJJOFDSA-N3.307 3 0 coronavir Ki (inhibitionmuM constant) 0.022 @@H](C[C@@H]1CCNC Replicase 1=O)C(=O)C1=NC2=CC= us CC=C2S1 polyprotein 1ab) [SARS coronavirus]

benzyl N-[(2S)-1-oxo-1- [(3S)-3-{[(2S)-1-oxo-3-[(3S)- 2-oxopyrrolidin-3-yl]-1- CC(C)NC(=O)C(=O)[C@H 3CL protease ](C[C@@H]1CCNC1=O) [(propan-2- Human NC(=O)[C@@H]1CC2(C [Human 3.3E+07 3.3E+07 7.6 yl)carbamoyl]propan-2- C36H46N6O7 674.797 BYAQBIUKMUHXDM-AMEOFWRWSA-N2.502 2 0 coronavir Inhibitor pIC50 no unit 7.6 CCC2)CN1C(=O)[C@H](C coronavirus C1=NC=CC=C1)NC(=O)O yl]carbamoyl}-2- us 229E 229E] CC1=CC=CC=C1 azaspiro[4.4]nonan-2-yl]-3- (pyridin-2-yl)propan-2- yl]carbamate 3C-like proteinase (cleavage SARS [H][C@](N)(CC1=CC=CC product of 1910408 1910408 7.52 63-91-2 L-phenylalanine C9H11NO2 165.192 COLNVLDHVKWLRT-QMMMGPOBSA-N0.84 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.03 protease from SARS-CoV =C1)C(O)=O Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase p-N,N- (cleavage dimethylaminobenzoic SARS CN(C)C1=CC=C(C=C1)C( product of 386867 386867 7.52 619-84-1 acid; 4- C9H11NO2 165.192 YDIYEOMDOWUDTJ-UHFFFAOYSA-N1.846 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.03 protease from SARS-CoV O)=O Replicase (Dimethylamino)benzoic us polyprotein 1ab) acid [SARS coronavirus]

3C-like proteinase (cleavage SARS NC1=C(Cl)C=C(C=C1)N(= product of 638657 638657 7.52 121-87-9 2-Chloro-4-nitroaniline C6H5ClN2O2 172.571 LOCWBQIWHWIRGN-UHFFFAOYSA-N1.719 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.03 protease from SARS-CoV O)=O Replicase us polyprotein 1ab) [SARS coronavirus]

Severe Acute Respiratory SARS ClC1=CN=CC(OC(=O)C2 1.9E+07 1.9E+07 7.52 1087243-14-8 C14H9ClN2O2272.691 BOSZJNSICHFHMA-UHFFFAOYSA-N3.047 4 2 Inhibitory concentrationIC50 nM of compound (dissolved in DMSO)30 against 3CL Protease from Severe Acute Respiratory Syndrome Coronavirus expressed in Escherichia coli BL21(DE3) upon incubation in 50 mM HEPES, pH 7.5 for 30 minutes at RT =C3C=CNC3=CC=C2)=C1 Syndrome-Cov coronavir 3Clpro [SARS us coronavirus]

Severe Acute Respiratory SARS ClC1=CN=CC(OC(=O)C2 1.9E+07 1.9E+07 7.52 1087243-14-8 C14H9ClN2O2272.691 BOSZJNSICHFHMA-UHFFFAOYSA-N3.047 4 2 Inhibitor Inhibitory concentrationIC50 nM of compound= against SEVERE ACUTE30 RESPIRATORY SYNDROME CORONAVIRUS 3CL PROTEASE (1 uM) using 100 uM ABZ-SVTLQSG-TYR(NO2)R as substrate upon incubation in 100 mM potassium phosphate, pH 8.0 at RT by FRET assay =C3C=CNC3=CC=C2)=C1 Syndrome-Cov coronavir 3Clpro [SARS us coronavirus]

3C-like proteinase (cleavage CN(C)C1=CC=C(C=C1)C( SARS =O)N[C@@H](CC1=CC= product of 1E+07 1E+07 7.52 C24H23ClN4O4466.924 NBBWJEWPUKPHPZ-QFIPXVFZSA-N4.859 4 2 coronavir Ki (inhibitionmuM constant) 0.03 CC=C1)C(=O)NC1=C(Cl)C Replicase =C(C=C1)N(=O)=O us polyprotein 1ab) [SARS coronavirus]

Severe Acute CNC1=CC=C(C=C1)C(=O) Respiratory SARS N[C@@H](CC1=CC=CC= 2.6E+07 2.6E+07 7.52 C23H21ClN4O4452.897 FQYWZMLECXJNLM-NRFANRHFSA-N4.296 4 2 Inhibitor Inhibition constantKi (inhibition againstmuM constant) Severe acute= respiratory syndrome-Corona0.03 virus 3C-like protein (SARS-CoV 3CLpro) using fluorogenic tetradecapeptide substrate C1)C(=O)NC1=CC=C(C=C Syndrome-Cov coronavir 1Cl)N(=O)=O 3Clpro [SARS us coronavirus]

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)[C@H](C) N)C(C)C)C(=O)N[C@@H Sars Cov 3C-Like SARS ](CCC(N)=O)C(=O)N[C@ 2.6E+07 2.6E+07 7.51 608531-54-0 C39H64N12O11877.011 MTHIRMPEXOAXGC-MVIFFEANSA-N-4.414 1 0 Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS-CoV0.031 3C-like protease @H](CO)C(=O)NCC(=O) Protease [SARS coronavir N[C@@H](CC1=CC=CC= coronavirus] us C1)C(=O)N[C@@H](CCC NC(N)=N)C(O)=O

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.5 C33H43F3N6O7S724.802 SQARSOUMWKXROA-ZJZGAYNASA-N3.306 2 0 Inhibitor pIC50 no unit 7.5 C(=O)[C@H](CC1=NC(=C 2-yl]carbamoyl}-3- [SARS coronavir S1)C(F)(F)F)NC(=O)OCC1 methylbutyl]carbamoyl}-2- coronavirus] us =CC=CC=C1 [4-(trifluoromethyl)-1,3- thiazol-2- yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) 3CL protease SARS NC(=O)[C@H](CC(C)C)N oxopyrrolidin-3-yl]propan- 3.3E+07 3.3E+07 7.5 C33H46N6O7S 670.83 GKSGNHPHNGKDME-CQJMVLFOSA-N1.908 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.5 C(=O)[C@H](CC1=NC=C( 2-yl]carbamoyl}-3- C)S1)NC(=O)OCC1=CC= coronavirus] us CC=C1 methylbutyl]carbamoyl}-2- (5-methyl-1,3-thiazol-2- yl)ethyl]carbamate benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- 3CL protease ](C[C@@H]1CCNC1=O) Human NC(=O)[C@H](CC(C)C)N oxopyrrolidin-3-yl]propan- [Human 3.3E+07 3.3E+07 7.5 C33H46N6O7S 670.83 GKSGNHPHNGKDME-CQJMVLFOSA-N1.908 2 0 coronavir Inhibitor pIC50 no unit 7.5 C(=O)[C@H](CC1=NC=C( 2-yl]carbamoyl}-3- coronavirus C)S1)NC(=O)OCC1=CC= us 229E CC=C1 methylbutyl]carbamoyl}-2- 229E] (5-methyl-1,3-thiazol-2- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.5 C35H48N6O7S696.868 JOVXDSIHEMZZIU-MNUOIFNESA-N2.266 2 0 Inhibitor pIC50 no unit 7.5 C(=O)[C@H](CC1=NC2= 2-yl]carbamoyl}-3- [SARS coronavir C(CCC2)S1)NC(=O)OCC1 methylbutyl]carbamoyl}-2- coronavirus] us =CC=CC=C1 {4H,5H,6H- cyclopenta[d][1,3]thiazol-2- yl}ethyl]carbamate

benzyl N-[(2S)-1- [(1S,3aR,6aS)-1-{[(2S)-1- [H][C@@]12CCC[C@]1([ oxo-3-[(3S)-2-oxopyrrolidin- H])[C@H](N(C2)C(=O)[C @H](CC1=CC=C(F)C=C1) 3-yl]-1-[(propan-2- 3CL protease SARS NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 7.5 yl)carbamoyl]propan-2- C36H44FN5O7677.773 GCSPVCXSCCUGET-HBESODNUSA-N3.159 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.5 1)C(=O)N[C@@H](C[C@ yl]carbamoyl}octahydrocyc coronavirus] us @H]1CCNC1=O)C(=O)C( =O)NC(C)C lopenta[c]pyrrol-2-yl]-3-(4- fluorophenyl)-1-oxopropan- 2-yl]carbamate

benzyl N-[(2S)-1- [(1S,3aR,6aS)-1-{[(2S)-1- [H][C@@]12CCC[C@]1([ oxo-3-[(3S)-2-oxopyrrolidin- H])[C@H](N(C2)C(=O)[C 3CL protease 3-yl]-1-[(propan-2- Human @H](CC1=CC=C(F)C=C1) [Human NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 7.5 yl)carbamoyl]propan-2- C36H44FN5O7677.773 GCSPVCXSCCUGET-HBESODNUSA-N3.159 2 0 coronavir Inhibitor pIC50 no unit 7.5 coronavirus 1)C(=O)N[C@@H](C[C@ yl]carbamoyl}octahydrocyc us 229E @H]1CCNC1=O)C(=O)C( 229E] =O)NC(C)C lopenta[c]pyrrol-2-yl]-3-(4- fluorophenyl)-1-oxopropan- 2-yl]carbamate

benzyl N-[(2S)-1-[(2S)-4,4- diethyl-2-{[(2S)-1-oxo-3- CCC1(CC)C[C@H](N(C1) [(3S)-2-oxopyrrolidin-3-yl]- 3CL protease C(=O)[C@H](CC1=CC=C( Human F)C=C1)NC(=O)OCC1=C 1-[(propan-2- [Human 3.3E+07 3.3E+07 7.5 C37H48FN5O7693.816 AFQMPDIGRFCOHN-SYKYGTKKSA-N4.166 2 0 coronavir Inhibitor pIC50 no unit 7.5 C=CC=C1)C(=O)N[C@@ yl)carbamoyl]propan-2- coronavirus H](C[C@@H]1CCNC1=O us 229E )C(=O)C(=O)NC(C)C yl]carbamoyl}pyrrolidin-1- 229E] yl]-3-(4-fluorophenyl)-1- oxopropan-2-yl]carbamate

benzyl N-[(2S)-1-[(2S)-4,4- diethyl-2-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CCC1(CC)C[C@H](N(C1) 1-[(propan-2- 3CL protease C(=O)[C@H](CN1CCC(C Human C1)C(F)(F)F)NC(=O)OCC yl)carbamoyl]propan-2- [Human 3.3E+07 3.3E+07 7.5 C37H53F3N6O7750.859 MXYZABAJFSFIJU-AMEOFWRWSA-N4.153 2 0 coronavir Inhibitor pIC50 no unit 7.5 1=CC=CC=C1)C(=O)N[C yl]carbamoyl}pyrrolidin-1- coronavirus @@H](C[C@@H]1CCNC us 229E 1=O)C(=O)C(=O)NC(C)C yl]-1-oxo-3-[4- 229E] (trifluoromethyl)piperidin- 1-yl]propan-2- yl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC=CC=C1)N C(=O)OCC1=CC=CC=C1) 1-{[(1S)-1- 3CL protease SARS C(=O)N[C@@H](C[C@@ 3.3E+07 3.3E+07 7.5 phenylethyl]carbamoyl}pr C38H46N6O7 698.819 NADDXCJMBHKEAV-OOZDRQTLSA-N3.575 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.5 H]1CCNC1=O)C(=O)C(= opan-2- coronavirus] us O)N[C@@H](C)C1=CC= CC=C1 yl]carbamoyl}butyl]carbam oyl}-2-(pyridin-2- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC=CC=C1)N 3CL protease 1-{[(1S)-1- Human C(=O)OCC1=CC=CC=C1) [Human C(=O)N[C@@H](C[C@@ 3.3E+07 3.3E+07 7.5 phenylethyl]carbamoyl}pr C38H46N6O7 698.819 NADDXCJMBHKEAV-OOZDRQTLSA-N3.575 2 0 coronavir Inhibitor pIC50 no unit 7.5 coronavirus H]1CCNC1=O)C(=O)C(= opan-2- us 229E O)N[C@@H](C)C1=CC= 229E] CC=C1 yl]carbamoyl}butyl]carbam oyl}-2-(pyridin-2- yl)ethyl]carbamate

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @H](CNC(=O)C(C)(C)C)N SARS C(=O)OCC1=CC=CC=C1) product of 2.5E+07 2.5E+07 7.42 TG-0204998 C32H47N5O7 613.754 YJBNUBPVCZONFM-QYOOZWMWSA-N2.304 2 0 coronavir Ki (inhibitionmuM constant) 0.038 C(=O)N[C@@H](C[C@@ Replicase H]1CCNC1=O)C=CC(C)= us O polyprotein 1ab) [SARS coronavirus]

Severe Acute OB(O)C1=CC(=CC(=C1)N Respiratory SARS (=O)=O)C(=O)NC1=CC=C 1.9E+07 1.9E+07 7.4 693235-40-4 C20H16B2N4O10493.99 JBHJLTFEEOIBFO-UHFFFAOYSA-N1.798 3 1 Radioligand (/ligand)Inhibition constantKi (inhibition againstmuM constant) Severe acute respiratory syndrome-Corona0.04 virus 3C-like protein (SARS-CoV 3CLpro) was determined (NC(=O)C2=CC(=CC(=C2) Syndrome-Cov coronavir B(O)O)N(=O)=O)C=C1 3Clpro [SARS us coronavirus] 3C-like proteinase (cleavage OB(O)C1=CC(=CC(=C1)N SARS (=O)=O)C(=O)NC1=CC=C product of 1.9E+07 1.9E+07 7.4 693235-40-4 C20H16B2N4O10493.99 JBHJLTFEEOIBFO-UHFFFAOYSA-N1.798 3 1 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.04 protease from SARS-CoV (NC(=O)C2=CC(=CC(=C2) Replicase B(O)O)N(=O)=O)C=C1 us polyprotein 1ab) [SARS coronavirus]

benzyl N-[(2S)-1-[(2S)-4,4- diethyl-2-{[(2S)-1-oxo-3- CCC1(CC)C[C@H](N(C1) [(3S)-2-oxopyrrolidin-3-yl]- C(=O)[C@H](CC1=CC=C( 3CL protease SARS F)C=C1)NC(=O)OCC1=C 1-[(propan-2- 3.3E+07 3.3E+07 7.4 C37H48FN5O7693.816 AFQMPDIGRFCOHN-SYKYGTKKSA-N4.166 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.4 C=CC=C1)C(=O)N[C@@ yl)carbamoyl]propan-2- H](C[C@@H]1CCNC1=O coronavirus] us )C(=O)C(=O)NC(C)C yl]carbamoyl}pyrrolidin-1- yl]-3-(4-fluorophenyl)-1- oxopropan-2-yl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(tert- butylcarbamoyl)-1-oxo-3- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CN(C)C)NC(=O)OC [(3S)-2-oxopyrrolidin-3- Human C1=CC=CC=C1)C(=O)N[C [Human 3.3E+07 3.3E+07 7.4 yl]propan-2-yl]carbamoyl}- C31H48N6O7 616.758 RBXUCWGAXPCWJY-ZJZGAYNASA-N1.787 2 0 coronavir Inhibitor pIC50 no unit 7.4 @@H](C[C@@H]1CCNC coronavirus 1=O)C(=O)C(=O)NC(C)(C 3-methylbutyl]carbamoyl}- us 229E 229E] )C 2- (dimethylamino)ethyl]carb amate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- 3CL protease @H](CN1CCCCC1)NC(= Human O)OCC1=CC=CC=C1)C(= 1-[(propan-2- [Human 3.3E+07 3.3E+07 7.4 C33H50N6O7 642.796 YAPXNEGFZWHFBS-FWEHEUNISA-N2.234 2 0 coronavir Inhibitor pIC50 no unit 7.4 O)N[C@@H](C[C@@H] yl)carbamoyl]propan-2- coronavirus 1CCNC1=O)C(=O)C(=O) us 229E NC(C)C yl]carbamoyl}butyl]carbam 229E] oyl}-2-(piperidin-1- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.4 C32H47F3N6O7684.756 DYBMFWIFLHGQAA-QORCZRPOSA-N3.262 2 0 Inhibitor pIC50 no unit 7.4 C(=O)[C@H](CN(C)CC(F) 2-yl]carbamoyl}-3- [SARS coronavir (F)F)NC(=O)OCC1=CC=C methylbutyl]carbamoyl}-2- coronavirus] us C=C1 [methyl(2,2,2- trifluoroethyl)amino]ethyl] carbamate

3C-like proteinase (cleavage SARS BrC1=CC(OC(=O)C2=CC= product of 1.1E+07 1.1E+07 7.3 936371-58-3 C10H6BrNO3 268.067 HMICIXHTRIFAET-UHFFFAOYSA-N1.77 4 2 coronavir IC50 nM 50 CO2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS BrC1=CC(OC(=O)C2=CC= product of 1.1E+07 1.1E+07 7.3 936371-58-3 C10H6BrNO3 268.067 HMICIXHTRIFAET-UHFFFAOYSA-N1.77 4 2 coronavir Inhibitor Inhibitory concentrationIC50 nM of compound= against SARS virus50 3C-like proteinase at 22 degree C using 20 mM Bis-TRIS as buffer, Abz-SVTLQSG-Tyr (NO2)R (10 uM) as substrate at pH 7.0 by fluorometric assay CO2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus] benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=CC(C)=CC=C1) 1-[(propan-2- 3CL protease SARS NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 7.3 C35H47N5O7 649.787 PVFWUORFJWPPGL-DZUOILHNSA-N3.822 2 0 Inhibitor pIC50 no unit 7.3 1)C(=O)N[C@@H](C[C@ yl)carbamoyl]propan-2- [SARS coronavir @H]1CCNC1=O)C(=O)C( yl]carbamoyl}butyl]carbam coronavirus] us =O)NC(C)C oyl}-2-(3- methylphenyl)ethyl]carba mate

benzyl ((S)-1-(((S)-1-(((S)-4- (isopropylamino)-3,4-dioxo- 1-((S)-2-oxopyrrolidin-3- yl)butan-2-yl)amino)-4- CC(C)C[C@H](NC(=O)[C methyl-1-oxopentan-2- @H](CN1CCC(CC1)C(F)( 3CL protease SARS F)F)NC(=O)OCC1=CC=CC yl)amino)-1-oxo-3-(4- 3.3E+07 3.3E+07 7.3 C34H49F3N6O7710.794 SACDDFOVSMEVSC-MNUOIFNESA-N3.533 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.3 =C1)C(=O)N[C@@H](C[ (trifluoromethyl)piperidin- C@@H]1CCNC1=O)C(= coronavirus] us O)C(=O)NC(C)C 1-yl)propan-2- yl)carbamate; benzyl N- [(1S)-1-{[(1S)-3-methyl-1- {[(2S)-1-oxo-3-[(3S)-2- oxopyrrolidin-3-yl]-1-

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.3 C35H45F3N6O8734.773 BRFLNKODYPAWQW-MNUOIFNESA-N4.584 2 0 Inhibitor pIC50 no unit 7.3 C(=O)[C@H](CC1=NC(O 2-yl]carbamoyl}-3- [SARS coronavir C(F)(F)F)=CC=C1)NC(=O) methylbutyl]carbamoyl}-2- coronavirus] us OCC1=CC=CC=C1 [6- (trifluoromethoxy)pyridin- 2-yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.3 C36H50N6O8 694.828 LLWOBJFCQNTMQC-AMEOFWRWSA-N3.769 2 0 Inhibitor pIC50 no unit 7.3 C(=O)[C@H](CC1=NC(O 2-yl]carbamoyl}-3- [SARS coronavir C)=CC(C)=C1)NC(=O)OC methylbutyl]carbamoyl}-2- coronavirus] us C1=CC=CC=C1 (6-methoxy-4- methylpyridin-2- yl)ethyl]carbamate

(4- {[cyclopropyl(methyl)amin

CC(C)C[C@H](NC(=O)[C o]methyl}phenyl)methyl N- @H](CC1=CC=C(F)C=C1) [(1S)-2-(4-fluorophenyl)-1- 3CL protease Human NC(=O)OCC1=CC=C(CN( {[(1S)-3-methyl-1-{[(2S)-1- [Human C)C2CC2)C=C1)C(=O)N[ 3.3E+07 3.3E+07 7.3 C39H53FN6O7736.884 MEQYIGWAROMELZ-XGKFQTDJSA-N3.84 2 0 coronavir Inhibitor pIC50 no unit 7.3 oxo-3-[(3S)-2-oxopyrrolidin- coronavirus C@@H](C[C@@H]1CCN us 229E C1=O)C(=O)C(=O)NC(C) 3-yl]-1-[(propan-2- 229E] C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-2- [(cyclopropylmethyl)(meth CC(C)C[C@H](NC(=O)[C yl)amino]-1-{[(1S)-3- @H](CN(C)CC1CC1)NC(= methyl-1-{[(2S)-1-oxo-3- 3CL protease SARS O)OCC1=CC=CC=C1)C(= 3.3E+07 3.3E+07 7.3 C33H50N6O7 642.796 KEVALLZBFLSUMS-FWEHEUNISA-N2.108 2 0 Inhibitor pIC50 no unit 7.3 O)N[C@@H](C[C@@H] [(3S)-2-oxopyrrolidin-3-yl]- [SARS coronavir 1CCNC1=O)C(=O)C(=O) 1-[(propan-2- coronavirus] us NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-2- [(cyclopropylmethyl)(meth yl)amino]-1-{[(1S)-3- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CN(C)CC1CC1)NC(= methyl-1-{[(2S)-1-oxo-3- Human O)OCC1=CC=CC=C1)C(= [Human 3.3E+07 3.3E+07 7.3 [(3S)-2-oxopyrrolidin-3-yl]- C33H50N6O7 642.796 KEVALLZBFLSUMS-FWEHEUNISA-N2.108 2 0 coronavir Inhibitor pIC50 no unit 7.3 O)N[C@@H](C[C@@H] coronavirus 1CCNC1=O)C(=O)C(=O) 1-[(propan-2- us 229E 229E] NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate benzyl N-[(1S)-3-methyl-1- {[(1S)-3-methyl-1-{[(2S)-1- CC(C)C[C@H](NC(=O)OC C1=CC=CC=C1)C(=O)N[C oxo-3-[(3S)-2-oxopyrrolidin- 3CL protease SARS @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 7.3 3-yl]-1-[(propan-2- C31H47N5O7 601.743 HEVXFSPURLYARR-QORCZRPOSA-N3.375 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.3 @@H](C[C@@H]1CCNC yl)carbamoyl]propan-2- coronavirus] us 1=O)C(=O)C(=O)NC(C)C yl]carbamoyl}butyl]carbam oyl}butyl]carbamate

benzyl N-[2-(6- methoxypyridin-2-yl)-1- COC1=CC=CC(CC(NC(=O {[(1S)-3-methyl-1-{[(2S)-1- 3CL protease )OCC2=CC=CC=C2)C(=O) Human N[C@@H](CC(C)C)C(=O) oxo-3-[(3S)-2-oxopyrrolidin- [Human 3.3E+07 3.3E+07 7.3 C34H46N6O8 666.775 QNSIYJPYGSKKOD-SNDIYCSQSA-N2.865 2 0 coronavir Inhibitor pIC50 no unit 7.3 N[C@@H](C[C@@H]2C 3-yl]-1-[(propan-2- coronavirus CNC2=O)C(=O)C(=O)NC( us 229E C)C)=N1 yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

3CLpro (3- O=C(CN1N=NC2=C1C=C chymotrypsin- SARS C=C2)N(CC1=CSC=C1)C1 2.4E+07 2.4E+07 7.29 C25H20N4OS 424.526 BRLBTOJQLXGOHO-UHFFFAOYSA-N4.926 4 2 IC50 muM 0.051 =CC=C(C=C1)C1=CC=CC like protease) coronavir =C1 [SARS us coronavirus]

3C-like proteinase (cleavage SARS BrC1=CC(OC(=O)C2=CC= product of 1.1E+07 1.1E+07 7.28 936371-58-3 C10H6BrNO3 268.067 HMICIXHTRIFAET-UHFFFAOYSA-N1.77 4 2 coronavir inhibition rate% 98 CO2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC=C(C=C1)C1=CC product of =C(O1)C(=O)OC1=CC(Cl) 1.1E+07 1.1E+07 7.28 C16H9Cl2NO3334.158 UICFGOSRHHZBHZ-UHFFFAOYSA-N4.169 4 2 coronavir inhibition rate% 98 Replicase =CN=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 7.28 C14H9ClN2O2272.691 LJTINUKMKJKLBT-UHFFFAOYSA-N3.06 4 2 coronavir inhibition rate% 99 =CC3=CC=CC=C3N2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 7.28 C14H8ClNO2S 289.742 MNUHXGJUYTWVLU-UHFFFAOYSA-N3.294 4 2 coronavir inhibition rate% 96 =CC3=CC=CC=C3S2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 7.28 C9H5ClN2O2S 240.67 CSEAAOWXHPFATP-UHFFFAOYSA-N1.798 4 2 coronavir inhibition rate% 98 =CSC=N2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS COC1=CC(=CC=C1)C(=O) product of 1.1E+07 1.1E+07 7.28 C13H10ClNO3 263.68 UIXQHURPUVBNCZ-UHFFFAOYSA-N2.809 4 2 coronavir inhibition rate% 97 OC1=CC(Cl)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(OC(C)(C)C)[C@H](NC (cleavage SARS (=O)OCC1=CC=CC=C1)C( product of =O)N[C@@H](CC1CCCC 2.4E+07 2.4E+07 7.28 TG-0205221 C32H48N4O7 600.756 coronavir Ki (inhibitionmuM constant) 0.053 Replicase C1)C(=O)N[C@@H](C[C us @@H]1CCNC1=O)C=O polyprotein 1ab) [SARS coronavirus]

3C-like [H]C(=O)[C@H](C[C@@ proteinase H]1CCNC1=O)NC(=O)[C (cleavage @H](CC1CCCCC1)NC(=O Coronavir 2.5E+07 2.5E+07 7.28 C32H48N4O7 600.756 YFUZVOLEKQFVCQ-SJSXQSQASA-N4.541 2 0 product of Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards Coronavirus0.053 (SARS CoV) GST-3C-like protease (75 nM) expressed in Escherichia coli using 15 uM SITSAVLQSGFRKMA substrate in 20 mM Tris-HCl (pH 7.5) at 25 degree C for 30 min )[C@@H](NC(=O)OCC1= idae CC=CC=C1)[C@H](C)OC( Replicase C)(C)C polyprotein 1ab) [Coronaviridae] 3C-like proteinase CC(OC(C)(C)C)[C@H](NC (cleavage SARS (=O)OCC1=CC=CC=C1)C( product of =O)N[C@@H](CC1CCCC 2.4E+07 2.4E+07 7.27 TG-0205221 C32H48N4O7 600.756 coronavir Ki (inhibitionmuM constant) 0.054 Replicase C1)C(=O)N[C@@H](C[C us @@H]1CCNC1=O)C=O polyprotein 1ab) [SARS coronavirus]

3C-like CCOC(=O)\C=C\[C@H](C proteinase [C@@H]1CCNC1=O)NC( (cleavage =O)[C@H](CC(C)C)NC(= Coronavir 2.5E+07 2.5E+07 7.24 C33H50N4O8 630.782 PWBQMVUCCVWDEJ-VVMRPRSSSA-N4.109 2 0 product of Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards Coronavirus0.058 (SARS CoV) GST-3C-like protease (75 nM) expressed in Escherichia coli using 15 uM SITSAVLQSGFRKMA substrate in 20 mM Tris-HCl (pH 7.5) at 25 degree C for 30 min O)[C@@H](NC(=O)OCC idae 1=CC=CC=C1)[C@H](C) Replicase OC(C)(C)C polyprotein 1ab) [Coronaviridae]

3C-like proteinase CCOC(=O)\C=C\[C@H](C (cleavage [C@@H]1CCNC1=O)NC( SARS =O)[C@H](CC(C)C)NC(= product of 2.4E+07 2.4E+07 7.24 C33H50N4O8 630.782 coronavir Ki (inhibitionmuM constant) 0.058 O)[C@@H](NC(=O)OCC Replicase 1=CC=CC=C1)C(C)OC(C)( us C)C polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CCOC(=O)C=C[C@H](C[ (cleavage C@@H]1CCNC1=O)CC(= SARS O)[C@H](CC(C)C)NC(=O) product of 2.5E+07 2.5E+07 7.24 TG-0203770 C34H51N3O8 629.794 JGQOJHCAERDGKI-DFCFLORXSA-N4.339 2 0 coronavir Ki (inhibitionmuM constant) 0.058 [C@@H](NC(=O)OCC1= Replicase CC=CC=C1)C(C)OC(C)(C) us C polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of 1.1E+07 1.1E+07 7.22 353257-73-5 C10H6ClNO3 223.616 DWJOEJDGHVXXEB-UHFFFAOYSA-N1.594 4 2 coronavir IC50 nM 60 CO2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of 1.1E+07 1.1E+07 7.22 353257-73-5 C10H6ClNO3 223.616 DWJOEJDGHVXXEB-UHFFFAOYSA-N1.594 4 2 coronavir Inhibitor Inhibitory concentrationIC50 nM of compound= against SARS virus60 3C-like proteinase at 22 degree C using 20 mM Bis-TRIS as buffer, Abz-SVTLQSG-Tyr (NO2)R (10 uM) as substrate at pH 7.0 by fluorometric assay CO2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage CN(C)C1=CC=C(C=C1)C( SARS =O)N[C@@H](CC1=CC= product of 1E+07 1E+07 7.22 C24H23ClN4O4466.924 NBBWJEWPUKPHPZ-QFIPXVFZSA-N4.859 4 2 coronavir IC50 muM 0.06 CC=C1)C(=O)NC1=C(Cl)C Replicase =C(C=C1)N(=O)=O us polyprotein 1ab) [SARS coronavirus]

Severe Acute CC(OC(C)(C)C)[C@H](NC (=O)OCC1=CC=CC=C1)C( Respiratory SARS =O)N[C@@H](CC1CCCC 1.4E+07 1.4E+07 7.22 C32H48N4O7 600.756 YFUZVOLEKQFVCQ-OKCRAPNYSA-N4.541 2 0 Syndrome-Cov coronavir Inhibition constantKi (inhibition of compoundnM constant) (dissolved~ in DMSO) towards60 3CL Protease from Severe Acute Respiratory Syndrome Coronavirus expressed in Escherichia coli BL21(DE3) upon incubation in 50 mM HEPES, pH 7.5 for 30 minutes at RT C1)C(=O)N[C@@H](C[C 3Clpro [SARS us @@H]1CCNC1=O)C=O coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of C(O2)C2=CC=C(C=C2)N( 1.6E+07 1.6E+07 7.22 1007551-98-5 C16H9ClN2O5344.711 KVPGYJGIPXOKGJ-UHFFFAOYSA-N3.439 4 2 coronavir IC50 nM 60 Replicase =O)=O)=CN=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)OCC1=CC SARS =CC=C1)C(C)C)C(=O)N[C product of 2.5E+07 2.5E+07 7.22 C35H43N5O6S661.822 PJDLIABGYBCSQU-QFVIIZQESA-N4.017 2 0 coronavir Ki (inhibitionmuM constant) 0.06 @@H](C[C@@H]1CCNC Replicase 1=O)C(=O)C1=NC=C(S1) us C1=CC=CC=C1 polyprotein 1ab) [SARS coronavirus]

Severe Acute CNC1=CC=C(C=C1)C(=O) Respiratory SARS N[C@@H](CC1=CC=CC= 2.6E+07 2.6E+07 7.22 C23H21ClN4O4452.897 FQYWZMLECXJNLM-NRFANRHFSA-N4.296 4 2 Inhibitor Inhibitory activityIC50 againstmuM Severe acute= respiratory syndrome-Corona0.06 virus 3C-like protein (SARS-CoV 3CLpro) using fluorogenic tetradecapeptide substrate C1)C(=O)NC1=CC=C(C=C Syndrome-Cov coronavir 1Cl)N(=O)=O 3Clpro [SARS us coronavirus] 3C-like proteinase (cleavage SARS ClC1=CC=C(C=C1)C1=CC product of =C(O1)C(=O)OC1=CC(Cl) 1.1E+07 1.1E+07 7.2 C16H9Cl2NO3334.158 UICFGOSRHHZBHZ-UHFFFAOYSA-N4.169 4 2 coronavir IC50 nM 63 Replicase =CN=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC=C(C=C1)C1=CC product of =C(O1)C(=O)OC1=CC(Cl) 1.1E+07 1.1E+07 7.2 C16H9Cl2NO3334.158 UICFGOSRHHZBHZ-UHFFFAOYSA-N4.169 4 2 coronavir Inhibitor Inhibitory concentrationIC50 nM of compound= against SARS virus63 3C-like proteinase at 22 degree C using 20 mM Bis-TRIS as buffer, Abz-SVTLQSG-Tyr (NO2)R (10 uM) as substrate at pH 7.0 by fluorometric assay Replicase =CN=C1 us polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-2-(5- fluoropyridin-2-yl)-1-{[(1S)- CC(C)C[C@H](NC(=O)[C 3-methyl-1-{[(2S)-1-oxo-3- 3CL protease @H](CC1=NC=C(F)C=C1) Human NC(=O)OCC1=CC=CC=C [(3S)-2-oxopyrrolidin-3-yl]- [Human 3.3E+07 3.3E+07 7.2 C33H43FN6O7654.739 PYRJSQGXJRFNSK-OXCFDMGDSA-N2.383 2 0 coronavir Inhibitor pIC50 no unit 7.2 1)C(=O)N[C@@H](C[C@ 1-[(propan-2- coronavirus @H]1CCNC1=O)C(=O)C( us 229E =O)NC(C)C yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC=C(C=C1)C 1-[(propan-2- 3CL protease SARS (F)(F)F)NC(=O)OCC1=CC 3.3E+07 3.3E+07 7.2 C34H43F3N6O7704.747 PVEAZVRGSPKZRQ-OXCFDMGDSA-N3.147 2 0 Inhibitor pIC50 no unit 7.2 =CC=C1)C(=O)N[C@@H] yl)carbamoyl]propan-2- [SARS coronavir (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam coronavirus] us (=O)C(=O)NC(C)C oyl}-2-[5- (trifluoromethyl)pyridin-2- yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CC1=NC=C(C=C1)C 1-[(propan-2- Human (F)(F)F)NC(=O)OCC1=CC [Human 3.3E+07 3.3E+07 7.2 yl)carbamoyl]propan-2- C34H43F3N6O7704.747 PVEAZVRGSPKZRQ-OXCFDMGDSA-N3.147 2 0 coronavir Inhibitor pIC50 no unit 7.2 =CC=C1)C(=O)N[C@@H] coronavirus (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam us 229E 229E] (=O)C(=O)NC(C)C oyl}-2-[5- (trifluoromethyl)pyridin-2- yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-{[(1S)-1- CC(C)C[C@H](NC(=O)[C cyclohexylethyl]carbamoyl @H](CC1=NC=CC=C1)N C(=O)OCC1=CC=CC=C1) }-1-oxo-3-[(3S)-2- 3CL protease SARS C(=O)N[C@@H](C[C@@ 3.3E+07 3.3E+07 7.2 oxopyrrolidin-3-yl]propan- C38H52N6O7 704.867 KIPIKDUHBLLVGS-OOZDRQTLSA-N4.244 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.2 H]1CCNC1=O)C(=O)C(= 2-yl]carbamoyl}-3- coronavirus] us O)N[C@@H](C)C1CCCC C1 methylbutyl]carbamoyl}-2- (pyridin-2- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC=CC(=C1)C 1-[(propan-2- 3CL protease SARS (F)(F)F)NC(=O)OCC1=CC 3.3E+07 3.3E+07 7.2 C34H43F3N6O7704.747 SUGDGIXBUPVGCE-OXCFDMGDSA-N3.147 2 0 Inhibitor pIC50 no unit 7.2 =CC=C1)C(=O)N[C@@H] yl)carbamoyl]propan-2- [SARS coronavir (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam coronavirus] us (=O)C(=O)NC(C)C oyl}-2-[4- (trifluoromethyl)pyridin-2- yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- 3CL protease ](C[C@@H]1CCNC1=O) Human NC(=O)[C@H](CC(C)C)N oxopyrrolidin-3-yl]propan- [Human 3.3E+07 3.3E+07 7.2 C32H44N6O7S656.803 CFEMQHZOVFHKGC-GKXKVECMSA-N2.756 2 0 coronavir Inhibitor pIC50 no unit 7.2 C(=O)[C@H](CC1=CSC= 2-yl]carbamoyl}-3- coronavirus N1)NC(=O)OCC1=CC=CC us 229E =C1 methylbutyl]carbamoyl}-2- 229E] (1,3-thiazol-4- yl)ethyl]carbamate benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- 3CL protease ](C[C@@H]1CCNC1=O) Human NC(=O)[C@H](CC(C)C)N oxopyrrolidin-3-yl]propan- [Human 3.3E+07 3.3E+07 7.2 C33H46N6O8S 686.83 JYGUFLMVCACERI-GKXKVECMSA-N2.663 2 0 coronavir Inhibitor pIC50 no unit 7.2 C(=O)[C@H](CC1=CSC(O 2-yl]carbamoyl}-3- coronavirus C)=N1)NC(=O)OCC1=CC us 229E =CC=C1 methylbutyl]carbamoyl}-2- 229E] (2-methoxy-1,3-thiazol-4- yl)ethyl]carbamate

{4-[2-(piperidin-1- yl)ethoxy]phenyl}methyl N-

CC(C)C[C@H](NC(=O)[C [(1S)-1-{[(1S)-1-{[(2S)-1- @H](CC1=CC=CC2=CC= (tert-butylcarbamoyl)-1- 3CL protease Human CC=C12)NC(=O)OCC1=C oxo-3-[(3S)-2-oxopyrrolidin- [Human C=C(OCCN2CCCCC2)C=C 3.3E+07 3.3E+07 7.2 C46H62N6O8 827.034 SLCZPZZDHCMRDX-RIPFCACWSA-N5.7 1 0 coronavir Inhibitor pIC50 no unit 7.2 3-yl]propan-2- coronavirus 1)C(=O)N[C@@H](C[C@ us 229E @H]1CCNC1=O)C(=O)C( yl]carbamoyl}-3- 229E] =O)NC(C)(C)C methylbutyl]carbamoyl}-2- (naphthalen-1- yl)ethyl]carbamate

benzyl ((S)-1-(((S)-1-(((S)-4- (isopropylamino)-3,4-dioxo- 1-((S)-2-oxopyrrolidin-3- yl)butan-2-yl)amino)-4- CC(C)C[C@H](NC(=O)[C methyl-1-oxopentan-2- @H](CC1=NC(=CC=C1)C 3CL protease SARS (F)(F)F)NC(=O)OCC1=CC yl)amino)-1-oxo-3-(6- 3.3E+07 3.3E+07 7.2 C34H43F3N6O7704.747 DQTFXZMNCOWPBY-GKXKVECMSA-N3.236 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.2 =CC=C1)C(=O)N[C@@H] (trifluoromethyl)pyridin-2- (C[C@@H]1CCNC1=O)C coronavirus] us (=O)C(=O)NC(C)C yl)propan-2-yl)carbamate; benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- 1-[(propan-2-

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1- (cyclopentylcarbamoyl)-1- CC(C)C[C@H](NC(=O)[C oxo-3-[(3S)-2-oxopyrrolidin- @H](CN1CCC(CC1)C(F)( 3CL protease SARS F)F)NC(=O)OCC1=CC=CC 3-yl]propan-2- 3.3E+07 3.3E+07 7.2 C36H51F3N6O7736.832 OWNQCYXBLVUHSK-JSRHHAARSA-N3.909 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.2 =C1)C(=O)N[C@@H](C[ yl]carbamoyl}-3- C@@H]1CCNC1=O)C(= coronavirus] us O)C(=O)NC1CCCC1 methylbutyl]carbamoyl}-2- [4- (trifluoromethyl)piperidin- 1-yl]ethyl]carbamate

benzyl N-[(1S)-2-(4- fluorophenyl)-1-{[(1S)-3- CC(C)C[C@H](NC(=O)[C methyl-1-{[(2S)-1-oxo-3- @H](CC1=CC=C(F)C=C1) 3CL protease SARS NC(=O)OCC1=CC=CC=C [(3S)-2-oxopyrrolidin-3-yl]- 3.3E+07 3.3E+07 7.2 C34H44FN5O7653.751 ZUZMPCWEWWIPQX-VNNZRSTGSA-N3.546 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.2 1)C(=O)N[C@@H](C[C@ 1-[(propan-2- @H]1CCNC1=O)C(=O)C( coronavirus] us =O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CCC1=CC=CC=C1)N 3CL protease SARS C(=O)OCC1=CC=CC=C1) 1-[(propan-2- 3.3E+07 3.3E+07 7.2 C35H47N5O7 649.787 MHOCJTNYGRIPAR-DZUOILHNSA-N3.743 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.2 C(=O)N[C@@H](C[C@@ yl)carbamoyl]propan-2- H]1CCNC1=O)C(=O)C(= coronavirus] us O)NC(C)C yl]carbamoyl}butyl]carbam oyl}-3- phenylpropyl]carbamate

3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 7.19 C14H9ClN2O2272.691 LJTINUKMKJKLBT-UHFFFAOYSA-N3.06 4 2 coronavir IC50 nM 65 =CC3=CC=CC=C3N2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus] 3C-like proteinase (cleavage CC(OC(C)(C)C)[C@H](NC (=O)OCC1=CC=CC=C1)C( product of Human =O)N[C@@H](CC1CCCC 2.4E+07 2.4E+07 7.17 TG-0205221 C32H48N4O7 600.756 Replicase coronavir Ki (inhibitionmuM constant) 0.068 C1)C(=O)N[C@@H](C[C polyprotein 1ab) us 229E @@H]1CCNC1=O)C=O [Human coronavirus 229E]

N-[(benzyloxy)carbonyl]-L- CC(C)C[C@H](NC(=O)[C valyl-N1-((1S)-2-hydroxy-1- Sars Cov 3C-Like @@H](NC(=O)OCC1=CC Coronavir =CC=C1)C(C)C)C(=O)N[C 1.5E+07 1.5E+07 7.17 890648-83-6 {[(3S)-2-oxopyrrolidin-3- C26H40N4O6 504.627 GLZAWCKOCLSXEU-CMOCDZPBSA-N2.111 3 0 Protease Inhibitor Inhibitory activityIC50 againstnM SARS-CoV= 3C-like protease catalyzed68 cleavage of TAMRA- SITSAVLQSGFRKMK-(DABCYL)-OH to TAMRA - SITSAVLQ and SGFRKMK- (DABCYL)-OH using 4.0 uM FRET substrate with the compound dissolved in 4 DMSO, pH 7.0 (HEPES buffer) idae @H](CO)C[C@@H]1CCN yl]methyl}ethyl)-L- [Coronaviridae] C1=O leucinamide

3C-like [H]C(=O)[C@H](C[C@@ proteinase H]1CCNC1=O)NC(=O)[C (cleavage @H](CC1CCCCC1)NC(=O Coronavir 2.5E+07 2.5E+07 7.17 C32H48N4O7 600.756 YFUZVOLEKQFVCQ-SJSXQSQASA-N4.541 2 0 product of Radioligand (/ligand)In vitro bindingKi (inhibition affinity towardsmuM constant) human= coronavirus 0.068229E (H-CoV 229E) 3C-like protease (75 nM) expressed in Escherichia coli using 15 uM substrate peptide VSYGSTLQAGLRKMA in 20 mM Tris-HCl (pH 7.5) at 25 degree C for 30 min )[C@@H](NC(=O)OCC1= idae CC=CC=C1)[C@H](C)OC( Replicase C)(C)C polyprotein 1ab) [Coronaviridae]

{4-[2-(piperidin-1- yl)ethoxy]phenyl}methyl N-

CC(C)C[C@H](NC(=O)[C [(1S)-1-{[(1S)-1-{[(2S)-1- @H](CC1=CC=CC2=CC= (tert-butylcarbamoyl)-1- 3CL protease SARS CC=C12)NC(=O)OCC1=C oxo-3-[(3S)-2-oxopyrrolidin- C=C(OCCN2CCCCC2)C=C 3.3E+07 3.3E+07 7.1 C46H62N6O8 827.034 SLCZPZZDHCMRDX-RIPFCACWSA-N5.7 1 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 3-yl]propan-2- 1)C(=O)N[C@@H](C[C@ coronavirus] us @H]1CCNC1=O)C(=O)C( yl]carbamoyl}-3- =O)NC(C)(C)C methylbutyl]carbamoyl}-2- (naphthalen-1- yl)ethyl]carbamate

(4- {[cyclopropyl(methyl)amin

CC(C)C[C@H](NC(=O)[C o]methyl}phenyl)methyl N- @H](CC1=CC=C(F)C=C1) [(1S)-2-(4-fluorophenyl)-1- 3CL protease SARS NC(=O)OCC1=CC=C(CN( {[(1S)-3-methyl-1-{[(2S)-1- C)C2CC2)C=C1)C(=O)N[ 3.3E+07 3.3E+07 7.1 C39H53FN6O7736.884 MEQYIGWAROMELZ-XGKFQTDJSA-N3.84 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 oxo-3-[(3S)-2-oxopyrrolidin- C@@H](C[C@@H]1CCN coronavirus] us C1=O)C(=O)C(=O)NC(C) 3-yl]-1-[(propan-2- C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

(5-methyl-1,2-oxazol-3- yl)methyl N-[(S)-{[(1S)-1- {[(2S)-1-(tert- CC(C)C[C@H](NC(=O)[C butylcarbamoyl)-1-oxo-3- @@H](NC(=O)OCC1=N 3CL protease SARS OC(C)=C1)C1CC2=CC=C [(3S)-2-oxopyrrolidin-3- 3.3E+07 3.3E+07 7.1 C35H48N6O8 680.802 BETCAOZGWASAGQ-WHHDSKRTSA-N2.793 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 C=C2C1)C(=O)N[C@@H] yl]propan-2-yl]carbamoyl}- (C[C@@H]1CCNC1=O)C coronavirus] us (=O)C(=O)NC(C)(C)C 3- methylbutyl]carbamoyl}(2, 3-dihydro-1H-inden-2- yl)methyl]carbamate

(5-methyl-1,2-oxazol-3- yl)methyl N-[(S)-{[(1S)-1- {[(2S)-1-(tert- CC(C)C[C@H](NC(=O)[C butylcarbamoyl)-1-oxo-3- 3CL protease @@H](NC(=O)OCC1=N Human OC(C)=C1)C1CC2=CC=C [(3S)-2-oxopyrrolidin-3- [Human 3.3E+07 3.3E+07 7.1 C35H48N6O8 680.802 BETCAOZGWASAGQ-WHHDSKRTSA-N2.793 2 0 coronavir Inhibitor pIC50 no unit 7.1 C=C2C1)C(=O)N[C@@H] yl]propan-2-yl]carbamoyl}- coronavirus (C[C@@H]1CCNC1=O)C us 229E (=O)C(=O)NC(C)(C)C 3- 229E] methylbutyl]carbamoyl}(2, 3-dihydro-1H-inden-2- yl)methyl]carbamate

benzyl N-[(2S)-1-oxo-1- [(3S)-3-{[(2S)-1-oxo-3-[(3S)- CC(C)NC(=O)C(=O)[C@H 2-oxopyrrolidin-3-yl]-1- ](C[C@@H]1CCNC1=O) [(propan-2- 3CL protease SARS NC(=O)[C@@H]1CC2(C 3.3E+07 3.3E+07 7.1 C36H46N6O7 674.797 BYAQBIUKMUHXDM-AMEOFWRWSA-N2.502 2 0 Inhibitor pIC50 no unit 7.1 CCC2)CN1C(=O)[C@H](C yl)carbamoyl]propan-2- [SARS coronavir C1=NC=CC=C1)NC(=O)O yl]carbamoyl}-2- coronavirus] us CC1=CC=CC=C1 azaspiro[4.4]nonan-2-yl]-3- (pyridin-2-yl)propan-2- yl]carbamate

benzyl ((S)-1-(((S)-1-(((S)-4- (isopropylamino)-3,4-dioxo- 1-((S)-2-oxopyrrolidin-3- yl)butan-2-yl)amino)-4- CC(C)C[C@H](NC(=O)[C methyl-1-oxopentan-2- 3CL protease @H](CC1=NC(=CC=C1)C Human (F)(F)F)NC(=O)OCC1=CC yl)amino)-1-oxo-3-(6- [Human 3.3E+07 3.3E+07 7.1 C34H43F3N6O7704.747 DQTFXZMNCOWPBY-GKXKVECMSA-N3.236 2 0 coronavir Inhibitor pIC50 no unit 7.1 =CC=C1)C(=O)N[C@@H] (trifluoromethyl)pyridin-2- coronavirus (C[C@@H]1CCNC1=O)C us 229E (=O)C(=O)NC(C)C yl)propan-2-yl)carbamate; 229E] benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- 1-[(propan-2- benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CN1CCCCC1)NC(= 3CL protease SARS O)OCC1=CC=CC=C1)C(= 1-[(propan-2- 3.3E+07 3.3E+07 7.1 C33H50N6O7 642.796 YAPXNEGFZWHFBS-FWEHEUNISA-N2.234 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 O)N[C@@H](C[C@@H] yl)carbamoyl]propan-2- 1CCNC1=O)C(=O)C(=O) coronavirus] us NC(C)C yl]carbamoyl}butyl]carbam oyl}-2-(piperidin-1- yl)ethyl]carbamate

benzyl N-[(1S)-2-(4,4- difluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- @H](CN1CCC(F)(F)CC1) 3CL protease SARS NC(=O)OCC1=CC=CC=C oxo-3-[(3S)-2-oxopyrrolidin- 3.3E+07 3.3E+07 7.1 C33H48F2N6O7678.777 FCTXOXQWSVOWIA-CQJMVLFOSA-N2.757 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 1)C(=O)N[C@@H](C[C@ 3-yl]-1-[(propan-2- @H]1CCNC1=O)C(=O)C( coronavirus] us =O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-2-(4,4- difluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- 3CL protease @H](CN1CCC(F)(F)CC1) Human NC(=O)OCC1=CC=CC=C oxo-3-[(3S)-2-oxopyrrolidin- [Human 3.3E+07 3.3E+07 7.1 C33H48F2N6O7678.777 FCTXOXQWSVOWIA-CQJMVLFOSA-N2.757 2 0 coronavir Inhibitor pIC50 no unit 7.1 1)C(=O)N[C@@H](C[C@ 3-yl]-1-[(propan-2- coronavirus @H]1CCNC1=O)C(=O)C( us 229E =O)NC(C)C yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-2-(4- fluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- 3CL protease @H](CN1CCC(F)CC1)NC( Human =O)OCC1=CC=CC=C1)C( oxo-3-[(3S)-2-oxopyrrolidin- [Human 3.3E+07 3.3E+07 7.1 C33H49FN6O7660.786 HLWOHQINQVCEIR-MNUOIFNESA-N2.378 2 0 coronavir Inhibitor pIC50 no unit 7.1 =O)N[C@@H](C[C@@H 3-yl]-1-[(propan-2- coronavirus ]1CCNC1=O)C(=O)C(=O) us 229E NC(C)C yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7.1 C35H51F3N6O7724.821 ZHJLTDNPCWVXNY-VNNZRSTGSA-N4 2 0 Inhibitor pIC50 no unit 7.1 C(=O)[C@H](CN1CCC(C 2-yl]carbamoyl}-3- [SARS coronavir C1)C(F)(F)F)NC(=O)OCC methylbutyl]carbamoyl}-2- coronavirus] us 1=CC=CC=C1 [4- (trifluoromethyl)piperidin- 1-yl]ethyl]carbamate

benzyl N-[(2S)-1-[(2S)-4,4- diethyl-2-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CCC1(CC)C[C@H](N(C1) 1-[(propan-2- C(=O)[C@H](CN1CCC(C 3CL protease SARS C1)C(F)(F)F)NC(=O)OCC yl)carbamoyl]propan-2- 3.3E+07 3.3E+07 7.1 C37H53F3N6O7750.859 MXYZABAJFSFIJU-AMEOFWRWSA-N4.153 2 0 [SARS coronavir Inhibitor pIC50 no unit 7.1 1=CC=CC=C1)C(=O)N[C yl]carbamoyl}pyrrolidin-1- @@H](C[C@@H]1CCNC coronavirus] us 1=O)C(=O)C(=O)NC(C)C yl]-1-oxo-3-[4- (trifluoromethyl)piperidin- 1-yl]propan-2- yl]carbamate

benzyl N-[(1S)-2-(4- fluorophenyl)-1-{[(1S)-3- CC(C)C[C@H](NC(=O)[C methyl-1-{[(2S)-1-oxo-3- 3CL protease @H](CC1=CC=C(F)C=C1) Human NC(=O)OCC1=CC=CC=C [(3S)-2-oxopyrrolidin-3-yl]- [Human 3.3E+07 3.3E+07 7.1 C34H44FN5O7653.751 ZUZMPCWEWWIPQX-VNNZRSTGSA-N3.546 2 0 coronavir Inhibitor pIC50 no unit 7.1 1)C(=O)N[C@@H](C[C@ 1-[(propan-2- coronavirus @H]1CCNC1=O)C(=O)C( us 229E =O)NC(C)C yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- 3CL protease @H](CCC1=CC=CC=C1)N Human C(=O)OCC1=CC=CC=C1) 1-[(propan-2- [Human 3.3E+07 3.3E+07 7.1 C35H47N5O7 649.787 MHOCJTNYGRIPAR-DZUOILHNSA-N3.743 2 0 coronavir Inhibitor pIC50 no unit 7.1 C(=O)N[C@@H](C[C@@ yl)carbamoyl]propan-2- coronavirus H]1CCNC1=O)C(=O)C(= us 229E O)NC(C)C yl]carbamoyl}butyl]carbam 229E] oyl}-3- phenylpropyl]carbamate

3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 7.02 C14H8ClNO2S 289.742 MNUHXGJUYTWVLU-UHFFFAOYSA-N3.294 4 2 coronavir IC50 nM 95 =CC3=CC=CC=C3S2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

Severe Acute CC(C)[C@H](NC(=O)[C@ @H](NC(C)=O)C(C)O)C(= Respiratory SARS O)N[C@@H](CC1CCCCC 2.4E+07 2.4E+07 7.01 C26H42N6O6 534.656 ZECWIGXEKGOONP-ASYUYLQXSA-N1.62 1 0 Syndrome-Cov coronavir Inhibitor Inhibitory concentrationIC50 nM of compound= against recombinant98 Severe acute respiratory syndrome coronavirus R188I mutant 3CL protease (120 nM) upon incubation in 40 mM Sodium acetate buffer, pH 4.0 1)C(=O)N[C@@H](CC1= 3Clpro [SARS us CNC=N1)C=O coronavirus]

CC(C)[C@H](NC(=O)[C@ @H](NC(C)=O)C(C)O)C(= SARS-CoV 3CL SARS O)N[C@@H](CC1CCCCC 2.4E+07 2.4E+07 7.01 C26H42N6O6 534.656 ZECWIGXEKGOONP-ASYUYLQXSA-N1.62 1 0 protease [SARS coronavir Inhibitor IC50 muM 0.098 1)C(=O)N[C@@H](CC1= coronavirus] us CNC=N1)C=O 3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)OCC1=CC SARS =CC=C1)C(C)OC(C)(C)C) product of 2.5E+07 2.5E+07 7 TG-0205486 C35H51N3O7 625.806 CPRMAACZQNGUOT-ILDWYHNZSA-N4.063 3 1 coronavir Ki (inhibitionmuM constant) 0.099 C(=O)C[C@@H](C[C@@ Replicase H]1CCNC1=O)C=CC(=O) us C1CC1 polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC(=CC=N1)C 1-[(propan-2- 3CL protease SARS (F)(F)F)NC(=O)OCC1=CC 3.3E+07 3.3E+07 7 C33H42F3N7O7705.734 FSEJHJVNCFRYOB-ZJZGAYNASA-N2.195 2 0 Inhibitor pIC50 no unit 7 =CC=C1)C(=O)N[C@@H] yl)carbamoyl]propan-2- [SARS coronavir (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam coronavirus] us (=O)C(=O)NC(C)C oyl}-2-[4- (trifluoromethyl)pyrimidin- 2-yl]ethyl]carbamate

benzyl N-[(1S)-2-(5- fluoropyridin-2-yl)-1-{[(1S)- CC(C)C[C@H](NC(=O)[C 3-methyl-1-{[(2S)-1-oxo-3- @H](CC1=NC=C(F)C=C1) 3CL protease SARS NC(=O)OCC1=CC=CC=C [(3S)-2-oxopyrrolidin-3-yl]- 3.3E+07 3.3E+07 7 C33H43FN6O7654.739 PYRJSQGXJRFNSK-OXCFDMGDSA-N2.383 2 0 [SARS coronavir Inhibitor pIC50 no unit 7 1)C(=O)N[C@@H](C[C@ 1-[(propan-2- @H]1CCNC1=O)C(=O)C( coronavirus] us =O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CC1=CC(C)=CC=C1) 1-[(propan-2- Human NC(=O)OCC1=CC=CC=C [Human 3.3E+07 3.3E+07 7 yl)carbamoyl]propan-2- C35H47N5O7 649.787 PVFWUORFJWPPGL-DZUOILHNSA-N3.822 2 0 coronavir Inhibitor pIC50 no unit 7 1)C(=O)N[C@@H](C[C@ coronavirus @H]1CCNC1=O)C(=O)C( yl]carbamoyl}butyl]carbam us 229E 229E] =O)NC(C)C oyl}-2-(3- methylphenyl)ethyl]carba mate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC(OC(F)(F)F) 1-[(propan-2- 3CL protease SARS =CC=C1)NC(=O)OCC1=C 3.3E+07 3.3E+07 7 C34H43F3N6O8720.746 SDGSGHDLEGVDQD-GKXKVECMSA-N4.117 2 0 Inhibitor pIC50 no unit 7 C=CC=C1)C(=O)N[C@@ yl)carbamoyl]propan-2- [SARS coronavir H](C[C@@H]1CCNC1=O yl]carbamoyl}butyl]carbam coronavirus] us )C(=O)C(=O)NC(C)C oyl}-2-[6- (trifluoromethoxy)pyridin- 2-yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease SARS NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 7 C34H44F3N7O7719.761 ICROBMCDYGRSIW-GKXKVECMSA-N2.573 2 0 Inhibitor pIC50 no unit 7 C(=O)[C@H](CC1=NC=C( 2-yl]carbamoyl}-3- [SARS coronavir C=N1)C(F)(F)F)NC(=O)O methylbutyl]carbamoyl}-2- coronavirus] us CC1=CC=CC=C1 [5- (trifluoromethyl)pyrimidin- 2-yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(tert- CC(C)C[C@H](NC(=O)[C butylcarbamoyl)-1-oxo-3- @H](CN(C)C)NC(=O)OC [(3S)-2-oxopyrrolidin-3- 3CL protease SARS C1=CC=CC=C1)C(=O)N[C 3.3E+07 3.3E+07 7 C31H48N6O7 616.758 RBXUCWGAXPCWJY-ZJZGAYNASA-N1.787 2 0 Inhibitor pIC50 no unit 7 @@H](C[C@@H]1CCNC yl]propan-2-yl]carbamoyl}- [SARS coronavir 1=O)C(=O)C(=O)NC(C)(C 3-methylbutyl]carbamoyl}- coronavirus] us )C 2- (dimethylamino)ethyl]carb amate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CN1CCOCC1)NC(= 3CL protease SARS O)OCC1=CC=CC=C1)C(= 1-[(propan-2- 3.3E+07 3.3E+07 7 C32H48N6O8 644.769 QPWPPKQBNBGAKA-CQJMVLFOSA-N0.97 2 0 [SARS coronavir Inhibitor pIC50 no unit 7 O)N[C@@H](C[C@@H] yl)carbamoyl]propan-2- 1CCNC1=O)C(=O)C(=O) coronavirus] us NC(C)C yl]carbamoyl}butyl]carbam oyl}-2-(morpholin-4- yl)ethyl]carbamate

benzyl N-[(1S)-2-(4- fluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- @H](CN1CCC(F)CC1)NC( 3CL protease SARS =O)OCC1=CC=CC=C1)C( oxo-3-[(3S)-2-oxopyrrolidin- 3.3E+07 3.3E+07 7 C33H49FN6O7660.786 HLWOHQINQVCEIR-MNUOIFNESA-N2.378 2 0 [SARS coronavir Inhibitor pIC50 no unit 7 =O)N[C@@H](C[C@@H 3-yl]-1-[(propan-2- ]1CCNC1=O)C(=O)C(=O) coronavirus] us NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1- (cyclopentylcarbamoyl)-1- CC(C)C[C@H](NC(=O)[C oxo-3-[(3S)-2-oxopyrrolidin- 3CL protease @H](CN1CCC(CC1)C(F)( Human F)F)NC(=O)OCC1=CC=CC 3-yl]propan-2- [Human 3.3E+07 3.3E+07 7 C36H51F3N6O7736.832 OWNQCYXBLVUHSK-JSRHHAARSA-N3.909 2 0 coronavir Inhibitor pIC50 no unit 7 =C1)C(=O)N[C@@H](C[ yl]carbamoyl}-3- coronavirus C@@H]1CCNC1=O)C(= us 229E O)C(=O)NC1CCCC1 methylbutyl]carbamoyl}-2- 229E] [4- (trifluoromethyl)piperidin- 1-yl]ethyl]carbamate benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(tert- CC(C)(C)NC(=O)C(=O)[C butylcarbamoyl)-1-oxo-3- @H](C[C@@H]1CCNC1 =O)NC(=O)[C@H](CC1C [(3S)-2-oxopyrrolidin-3- 3CL protease SARS CCC1)NC(=O)[C@H](CC1 3.3E+07 3.3E+07 7 yl]propan-2-yl]carbamoyl}- C40H50N6O7 726.873 VCUZBAJGPFKDDV-XGKFQTDJSA-N4.703 2 0 [SARS coronavir Inhibitor pIC50 no unit 7 =C2C=CC=NC2=CC=C1) 2- coronavirus] us NC(=O)OCC1=CC=CC=C 1 cyclopentylethyl]carbamoy l}-2-(quinolin-5- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(tert- CC(C)(C)NC(=O)C(=O)[C butylcarbamoyl)-1-oxo-3- @H](C[C@@H]1CCNC1 3CL protease [(3S)-2-oxopyrrolidin-3- Human =O)NC(=O)[C@H](CC1C [Human CCC1)NC(=O)[C@H](CC1 3.3E+07 3.3E+07 7 yl]propan-2-yl]carbamoyl}- C40H50N6O7 726.873 VCUZBAJGPFKDDV-XGKFQTDJSA-N4.703 2 0 coronavir Inhibitor pIC50 no unit 7 coronavirus =C2C=CC=NC2=CC=C1) 2- us 229E NC(=O)OCC1=CC=CC=C 229E] 1 cyclopentylethyl]carbamoy l}-2-(quinolin-5- yl)ethyl]carbamate

benzyl N-[(1S)-3-methyl-1- {[(1S)-3-methyl-1-{[(2S)-1- CC(C)C[C@H](NC(=O)OC 3CL protease oxo-3-[(3S)-2-oxopyrrolidin- Human C1=CC=CC=C1)C(=O)N[C [Human @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 7 3-yl]-1-[(propan-2- C31H47N5O7 601.743 HEVXFSPURLYARR-QORCZRPOSA-N3.375 2 0 coronavir Inhibitor pIC50 no unit 7 coronavirus @@H](C[C@@H]1CCNC yl)carbamoyl]propan-2- us 229E 1=O)C(=O)C(=O)NC(C)C 229E] yl]carbamoyl}butyl]carbam oyl}butyl]carbamate

benzyl N-[2-(6- methoxypyridin-2-yl)-1- COC1=CC=CC(CC(NC(=O {[(1S)-3-methyl-1-{[(2S)-1- )OCC2=CC=CC=C2)C(=O) 3CL protease SARS N[C@@H](CC(C)C)C(=O) oxo-3-[(3S)-2-oxopyrrolidin- 3.3E+07 3.3E+07 7 C34H46N6O8 666.775 QNSIYJPYGSKKOD-SNDIYCSQSA-N2.865 2 0 [SARS coronavir Inhibitor pIC50 no unit 7 N[C@@H](C[C@@H]2C 3-yl]-1-[(propan-2- CNC2=O)C(=O)C(=O)NC( coronavirus] us C)C)=N1 yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

3C-like proteinase (cleavage 5-chloro-3-pyridyl 2-oxo- SARS ClC1=CN=CC(OC(=O)C2 product of =CC3=CC=CC=C3OC2=O 8492554 8492554 6.97 2H-1-benzopyran-3- C15H8ClNO4 301.686 SGHKVFYMZNVFKN-UHFFFAOYSA-N2.564 4 2 coronavir IC50 nM 108 Replicase )=C1 carboxylate us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS NC(=O)C1=CC=C2N(CC3 product of =CC4=C(C=CC=C4)C=C3) 7597721 7597721 6.92 C20H14N2O3 330.343 NTNYHMJYSGPGCQ-UHFFFAOYSA-N2.59 4 2 coronavir Ki (inhibitionM constant) 1.20E-07 Replicase C(=O)C(=O)C2=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=C3C product of =CC=CC3=CC=C2)=CN=C 1.6E+07 1.6E+07 6.91 1007552-07-9 C16H10ClNO2283.714 MBLPTPFVBVNBEX-UHFFFAOYSA-N4.16 4 2 coronavir IC50 nM 124 Replicase 1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(=C(C=C1)C1=C product of C=C(O1)C(=O)OC1=CN= 1.6E+07 1.6E+07 6.91 1007551-99-6 C16H8Cl2N2O5379.156 YEGHZGNCUKGRIS-UHFFFAOYSA-N4.061 4 2 coronavir IC50 nM 122 Replicase CC(Cl)=C1)N(=O)=O us polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CC1=NC=CC(=C1)C 1-[(propan-2- Human (F)(F)F)NC(=O)OCC1=CC [Human 3.3E+07 3.3E+07 6.9 yl)carbamoyl]propan-2- C34H43F3N6O7704.747 SUGDGIXBUPVGCE-OXCFDMGDSA-N3.147 2 0 coronavir Inhibitor pIC50 no unit 6.9 =CC=C1)C(=O)N[C@@H] coronavirus (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam us 229E 229E] (=O)C(=O)NC(C)C oyl}-2-[4- (trifluoromethyl)pyridin-2- yl]ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- 1-oxo-3-[(3S)-2- CCCCNC(=O)C(=O)[C@H 3CL protease ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- Human NC(=O)[C@H](CC(C)C)N [Human 3.3E+07 3.3E+07 6.9 2-yl]carbamoyl}-3- C34H44F3N7O7719.761 ICROBMCDYGRSIW-GKXKVECMSA-N2.573 2 0 coronavir Inhibitor pIC50 no unit 6.9 C(=O)[C@H](CC1=NC=C( coronavirus C=N1)C(F)(F)F)NC(=O)O methylbutyl]carbamoyl}-2- us 229E 229E] CC1=CC=CC=C1 [5- (trifluoromethyl)pyrimidin- 2-yl]ethyl]carbamate benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- 3CL protease @H](CN1CCOCC1)NC(= Human O)OCC1=CC=CC=C1)C(= 1-[(propan-2- [Human 3.3E+07 3.3E+07 6.9 C32H48N6O8 644.769 QPWPPKQBNBGAKA-CQJMVLFOSA-N0.97 2 0 coronavir Inhibitor pIC50 no unit 6.9 O)N[C@@H](C[C@@H] yl)carbamoyl]propan-2- coronavirus 1CCNC1=O)C(=O)C(=O) us 229E NC(C)C yl]carbamoyl}butyl]carbam 229E] oyl}-2-(morpholin-4- yl)ethyl]carbamate

benzyl N-[(1S,2S)-2- methoxy-1-{[(1S)-3-methyl- CO[C@@H](C)[C@H](N 1-{[(2S)-1-oxo-3-[(3S)-2- 3CL protease C(=O)OCC1=CC=CC=C1) Human C(=O)N[C@@H](CC(C)C) oxopyrrolidin-3-yl]-1- [Human 3.3E+07 3.3E+07 6.9 C30H45N5O8 603.716 LYNTYGQCINXZAN-DUSBTPNUSA-N1.787 2 0 coronavir Inhibitor pIC50 no unit 6.9 C(=O)N[C@@H](C[C@@ [(propan-2- coronavirus H]1CCNC1=O)C(=O)C(= us 229E O)NC(C)C yl)carbamoyl]propan-2- 229E] yl]carbamoyl}butyl]carbam oyl}propyl]carbamate

benzyl N-[(1S)-2- [(cyclopropylmethyl)(meth CC(C)C[C@H](NC(=O)[C yl)amino]-1-{[(1S)-3- @H](CN(C)CC1CC1)NC(= methyl-1-{[(2S)-1-oxo-3- O)OCC1=CC=CC=C1)C(= 3CL protease Coronavir 3.3E+07 3.3E+07 6.84 [(3S)-2-oxopyrrolidin-3-yl]- C33H50N6O7 642.796 KEVALLZBFLSUMS-FWEHEUNISA-N2.108 2 0 Inhibitor pIC50 no unit 6.84 O)N[C@@H](C[C@@H] [Coronavirinae] inae 1CCNC1=O)C(=O)C(=O) 1-[(propan-2- NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

[Na+].OC([C@H](C[C@ @H]1CCNC1=O)NC(=O)[ 3C-like protease Coronavir C@H](CC1CCCCC1)NC(= 3.2E+07 3.2E+07 6.82 C24H33ClN3O8S*Na582.05 QBZITZQGIUHVSG-GAPUZUELSA-M2.314 2 0 Inhibitor IC50 muM 0.15 O)OCC1=CC(Cl)=CC=C1) [Coronavirinae] inae S([O-])(=O)=O

C[C@@H](N1CCC(CC1)C (R)-N-(3-fluorobenzyl)-1-(1- Papain-like SARS (=O)NCC1=CC(F)=CC=C1 2.7E+07 2.7E+07 6.82 1581755-45-4 C25H27FN2O 390.501 XJTWGMHOQKGBDO-GOSISDBHSA-N5.142 3 2 IC50 muM 0.15 )C1=CC=CC2=CC=CC=C1 (naphthalen-1-yl)ethyl)- protease [SARS coronavir 2 piperidine-4-carboxamide coronavirus] us

Severe Acute (Pyridin-3- Respiratory SARS ClC1=CC(CSC(=S)NCC2= ylmethyl)dithiocarbamic 1.4E+07 1.4E+07 6.8 370065-68-2 C12H10Cl2N2S3349.329 DGYDYUNBWSVWEX-UHFFFAOYSA-N2.528 4 2 Syndrome-Cov coronavir Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS0.16 CORONAVIRUS 3CL PROTEASE upon incubation in 50 mM HEPES, pH 7.5 for 1 hr at RT was determined CC=CN=C2)=C(Cl)S1 acid 2,5-dichloro-thiophen- 3Clpro [SARS us 3-ylmethyl ester coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CC1=NC(=CC=N1)C 1-[(propan-2- Human (F)(F)F)NC(=O)OCC1=CC [Human 3.3E+07 3.3E+07 6.8 yl)carbamoyl]propan-2- C33H42F3N7O7705.734 FSEJHJVNCFRYOB-ZJZGAYNASA-N2.195 2 0 coronavir Inhibitor pIC50 no unit 6.8 =CC=C1)C(=O)N[C@@H] coronavirus (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam us 229E 229E] (=O)C(=O)NC(C)C oyl}-2-[4- (trifluoromethyl)pyrimidin- 2-yl]ethyl]carbamate

benzyl N-[(1S)-2-(4,4- difluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- @H](CN1CCC(F)(F)CC1) oxo-3-[(3S)-2-oxopyrrolidin- 3CL protease Coronavir NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 6.8 C33H48F2N6O7678.777 FCTXOXQWSVOWIA-CQJMVLFOSA-N2.757 2 0 Inhibitor pIC50 no unit 6.8 1)C(=O)N[C@@H](C[C@ 3-yl]-1-[(propan-2- [Coronavirinae] inae @H]1CCNC1=O)C(=O)C( =O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- 1-oxo-3-[(3S)-2- CCCCNC(=O)C(=O)[C@H 3CL protease ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- Human NC(=O)[C@H](CC(C)C)N [Human 3.3E+07 3.3E+07 6.8 2-yl]carbamoyl}-3- C35H51F3N6O7724.821 ZHJLTDNPCWVXNY-VNNZRSTGSA-N4 2 0 coronavir Inhibitor pIC50 no unit 6.8 C(=O)[C@H](CN1CCC(C coronavirus C1)C(F)(F)F)NC(=O)OCC methylbutyl]carbamoyl}-2- us 229E 229E] 1=CC=CC=C1 [4- (trifluoromethyl)piperidin- 1-yl]ethyl]carbamate benzyl N-[(1S,2S)-2- methoxy-1-{[(1S)-3-methyl- CO[C@@H](C)[C@H](N 1-{[(2S)-1-oxo-3-[(3S)-2- C(=O)OCC1=CC=CC=C1) 3CL protease SARS C(=O)N[C@@H](CC(C)C) oxopyrrolidin-3-yl]-1- 3.3E+07 3.3E+07 6.8 C30H45N5O8 603.716 LYNTYGQCINXZAN-DUSBTPNUSA-N1.787 2 0 [SARS coronavir Inhibitor pIC50 no unit 6.8 C(=O)N[C@@H](C[C@@ [(propan-2- H]1CCNC1=O)C(=O)C(= coronavirus] us O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}propyl]carbamate

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of 1.6E+07 1.6E+07 6.79 1007552-02-4 C11H7ClN2O2234.642 DPPNJVAWFLHUGI-UHFFFAOYSA-N1.642 4 2 coronavir IC50 nM 164 NC=C2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

zinc pyrithione; 1- hydroxypyridine-2-thione, Zn(II) complex; bis(N- oxopyridine-2-thionato) Sars Cov 3C-Like SARS [Zn++].[S- 1.1E+07 1.1E+07 6.77 13463-41-7 2C5H4NOS*Zn317.708 PURMLSMXFJKREH-UHFFFAOYSA-M1.645 4 2 Radioligand (/ligand)Binding affinityKi (inhibition of the compoundmuM constant) towards= SARS-CoV 3C-like0.17 protease ]C1=N(=O)C=CC=C1 zinc(II); 1-hydroxypyridine- Protease [SARS coronavir 2-thione zinc salt; zinc 2- coronavirus] us mercaptopyridine N-oxide; pyrithione zinc; zinc- pyrithion

zinc pyrithione; 1- 3C-like hydroxypyridine-2-thione, proteinase Zn(II) complex; bis(N- (cleavage oxopyridine-2-thionato) SARS [Zn++].[S- product of 1.1E+07 1.1E+07 6.77 13463-41-7 zinc(II); 1-hydroxypyridine- 2C5H4NOS*Zn317.708 PURMLSMXFJKREH-UHFFFAOYSA-M1.645 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.17 protease from SARS-CoV ]C1=N(=O)C=CC=C1 Replicase 2-thione zinc salt; zinc 2- us polyprotein 1ab) mercaptopyridine N-oxide; [SARS pyrithione zinc; zinc- coronavirus] pyrithion

pyrithione zinc; 2- pyridylthiol-1-oxide zinc; Pyrithione zinc; 1- Severe Acute

S1C2=CC=CC=N2=[O][Zn hydroxypyridine-2-thione Respiratory SARS ]11SC2=N(C=CC=C2)=[O 1.1E+07 1.1E+07 6.77 zinc salt; bis(2- C10H8N2O2S2Zn317.708 OTPSWLRZXRHDNX-UHFFFAOYSA-L3 2 Syndrome-Cov coronavir Inhibitor Inhibition constantKi (inhibition againstmuM constant) Severe acute= respiratory syndrome-Corona0.17 virus 3C-like protein (SARS-CoV 3CLpro) was measured; Competitive inhibition ]1 pyridylthio)zinc 1,1'- 3Clpro [SARS us dioxide; 1-hydroxypyridine- coronavirus] 2-thione zinc; bis(2- pyridylthio-1-oxide)zinc

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC3 product of =C(O2)C=CC=C3)=CN=C 1.1E+07 1.1E+07 6.77 C14H8ClNO3 273.675 QHBWMDVARYUYJW-UHFFFAOYSA-N2.95 4 2 coronavir IC50 nM 170 Replicase 1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS (=CC=C1)N(C)C)C(C)C)C( product of 2.5E+07 2.5E+07 6.77 C37H48N6O6S704.891 SAUDUBFZQXQOPS-IAGMFGRWSA-N3.744 2 0 coronavir Ki (inhibitionmuM constant) 0.17 =O)N[C@@H](C[C@@H Replicase ]1CCNC1=O)C(=O)C1=N us C=C(S1)C1=CC=CC=C1 polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- NC(=O)[C@H](CC(C)C)N 3CL protease Coronavir 3.3E+07 3.3E+07 6.71 2-yl]carbamoyl}-3- C35H51F3N6O7724.821 ZHJLTDNPCWVXNY-VNNZRSTGSA-N4 2 0 Inhibitor pIC50 no unit 6.71 C(=O)[C@H](CN1CCC(C [Coronavirinae] inae C1)C(F)(F)F)NC(=O)OCC methylbutyl]carbamoyl}-2- 1=CC=CC=C1 [4- (trifluoromethyl)piperidin- 1-yl]ethyl]carbamate

RNA dependent Middle (1R,2S,3S,4R,5R)-3-(6- RNA polymerase East amino-9H-purin-9-yl)-4- [Middle East respirator NC1=NC=NC2=C1N=CN fluoro-5- respiratory 2[C@H]1[C@H](O)[C@H y 1E+07 1E+07 6.7 (hydroxymethyl)cyclopent C11H14FN5O3283.262 LFSGVDMIBZBPPJ-QCFOWSJWSA-N-0.667 4 2 syndrome Inhibitor EC50 muM 0.2 ](O)[C@@H](CO)[C@H] syndrome 1F ane-1,2-diol; (-)-6?-beta- coronavirus]; coronavir fluoro-aristeromycin; 6'- Adenosylhomoc us; beta-fluoroaristeromycin ysteinase human [human]

sodium (2S)-2-{(S)-2-[({[1- Middle (tert- 3C-like protease East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- [Middle East respirator =O)OC1CCN(CC1)C(=O) 4-yl]oxy} carbonyl)amino]- OC(C)(C)C)C(=O)N[C@@ 3.2E+07 3.2E+07 6.7 C24H41N4O10S*Na600.666 MVNGOUPOTIVRRK-FCSMXUNPSA-M0.271 2 0 respiratory y Inhibitor EC50 muM 0.2 4-methylpentanamido}-1- H](C[C@@H]1CCNC1=O syndrome syndrome )C(O)S([O-])(=O)=O hydroxy-3-[(S)-2- coronavirus] coronavir oxopyrrolidin-3-yl]propane- us 1-sulfonate

RNA dependent Middle RNA polymerase (1R,2S,3S,5R)-3-(6-amino- East [Middle East 9H-purin-9-yl)-4,4-difluoro- respirator NC1=C2N=CN([C@H]3[C respiratory @H](O)[C@H](O)[C@@ 5- y 3.5E+07 3.5E+07 6.7 C11H13F2N5O3301.253 XSXKATMUCWUUFZ-JBBNEOJLSA-N-0.288 4 2 syndrome Inhibitor EC50 muM 0.2 H](CO)C3(F)F)C2=NC=N (hydroxymethyl)cyclopent syndrome 1 coronavirus]; ane-1,2-diol; 6',6'- coronavir Adenosylhomoc difluoroaristeromycin us; ysteinase human [human] 3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of C(O2)C2=C(C=CC=C2)N( 1.6E+07 1.6E+07 6.68 1007552-00-2 C16H9ClN2O5344.711 OGRUFOQJVSKQTN-UHFFFAOYSA-N3.439 4 2 coronavir IC50 nM 208 Replicase =O)=O)=CN=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS =CN=C1)C(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 6.66 1383922-92-6 C32H40N6O6S636.772 VOKLNKGFAWURBK-GGHZGINBSA-N2.055 2 0 coronavir Ki (inhibitionmuM constant) 0.22 @@H](C[C@@H]1CCNC Replicase 1=O)C(=O)C1=NC2=CC= us CC=C2S1 polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)CNC1=CC SARS =CC=C1)C(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 6.66 1383922-55-1 C33H42N6O5S 634.8 PPHLPUPOOAKMQM-WWZJJOFDSA-N3.038 2 0 coronavir Ki (inhibitionmuM constant) 0.22 @@H](C[C@@H]1CCNC Replicase 1=O)C(=O)C1=NC2=CC= us CC=C2S1 polyprotein 1ab) [SARS coronavirus]

benzyl ((S)-1-(((S)-1-(((S)-4- (isopropylamino)-3,4-dioxo- 1-((S)-2-oxopyrrolidin-3- yl)butan-2-yl)amino)-4- CC(C)C[C@H](NC(=O)[C @H](CN1CCC(CC1)C(F)( methyl-1-oxopentan-2- F)F)NC(=O)OCC1=CC=CC yl)amino)-1-oxo-3-(4- 3CL protease Coronavir 3.3E+07 3.3E+07 6.66 C34H49F3N6O7710.794 SACDDFOVSMEVSC-MNUOIFNESA-N3.533 2 0 Inhibitor pIC50 no unit 6.66 =C1)C(=O)N[C@@H](C[ (trifluoromethyl)piperidin- [Coronavirinae] inae C@@H]1CCNC1=O)C(= O)C(=O)NC(C)C 1-yl)propan-2- yl)carbamate; benzyl N- [(1S)-1-{[(1S)-3-methyl-1- {[(2S)-1-oxo-3-[(3S)-2- oxopyrrolidin-3-yl]-1-

3C-like (1-{3-methyl-1-[2-oxo-1-(2- proteinase oxo-pyrrolidin-3- CC(C)C[C@H](NC(=O)[C (cleavage @H](CC1=CC=CC2=C1C ylmethyl)ethylcarbamoyl]b SARS =CC=C2)NC(=O)OCC1=C product of 2.4E+07 2.4E+07 6.64 utylcarbamoyl}-2- C34H40N4O6 600.715 UULYLRNRQOWCOR-ZHTHUIBPSA-N4.738 3 0 coronavir IC50 muM 0.23 C=CC=C1)C(=O)N[C@@ Replicase H](C[C@@H]1CCNC1=O naphthalen-1-yl- us polyprotein 1ab) )C=O ethyl)carbamic acid benzyl [SARS ester coronavirus]

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-{[(1S)-1- CC(C)C[C@H](NC(=O)[C cyclohexylethyl]carbamoyl @H](CC1=NC=CC=C1)N 3CL protease }-1-oxo-3-[(3S)-2- Human C(=O)OCC1=CC=CC=C1) [Human C(=O)N[C@@H](C[C@@ 3.3E+07 3.3E+07 6.6 oxopyrrolidin-3-yl]propan- C38H52N6O7 704.867 KIPIKDUHBLLVGS-OOZDRQTLSA-N4.244 2 0 coronavir Inhibitor pIC50 no unit 6.6 coronavirus H]1CCNC1=O)C(=O)C(= 2-yl]carbamoyl}-3- us 229E O)N[C@@H](C)C1CCCC 229E] C1 methylbutyl]carbamoyl}-2- (pyridin-2- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- CC(C)C[C@H](NC(=O)[C 3CL protease @H](CC1=NC(OC(F)(F)F) 1-[(propan-2- Human =CC=C1)NC(=O)OCC1=C [Human 3.3E+07 3.3E+07 6.6 yl)carbamoyl]propan-2- C34H43F3N6O8720.746 SDGSGHDLEGVDQD-GKXKVECMSA-N4.117 2 0 coronavir Inhibitor pIC50 no unit 6.6 C=CC=C1)C(=O)N[C@@ coronavirus H](C[C@@H]1CCNC1=O yl]carbamoyl}butyl]carbam us 229E 229E] )C(=O)C(=O)NC(C)C oyl}-2-[6- (trifluoromethoxy)pyridin- 2-yl]ethyl]carbamate

{4-[3-(morpholin-4- yl)propoxy]phenyl}methyl

CC(C)(C)NC(=O)C(=O)[C N-[(1S)-1-{[(1S)-1-{[(2S)-1- @H](C[C@@H]1CCNC1 (tert-butylcarbamoyl)-1- 3CL protease SARS =O)NC(=O)[C@H](CC1C oxo-3-[(3S)-2-oxopyrrolidin- CCCC1)NC(=O)[C@H](C 3.3E+07 3.3E+07 6.6 C49H66N6O9 883.098 RKUQPVSRHDTBRE-HPSVALOHSA-N6.161 1 0 [SARS coronavir Inhibitor pIC50 no unit 6.6 3-yl]propan-2- C1=CC=CC2=CC=CC=C1 coronavirus] us 2)NC(=O)OCC1=CC=C(O yl]carbamoyl}-2- CCCN2CCOCC2)C=C1 cyclohexylethyl]carbamoyl }-2-(naphthalen-1- yl)ethyl]carbamate

{4-[3-(morpholin-4- yl)propoxy]phenyl}methyl

CC(C)(C)NC(=O)C(=O)[C N-[(1S)-1-{[(1S)-1-{[(2S)-1- @H](C[C@@H]1CCNC1 (tert-butylcarbamoyl)-1- 3CL protease Human =O)NC(=O)[C@H](CC1C oxo-3-[(3S)-2-oxopyrrolidin- [Human CCCC1)NC(=O)[C@H](C 3.3E+07 3.3E+07 6.6 C49H66N6O9 883.098 RKUQPVSRHDTBRE-HPSVALOHSA-N6.161 1 0 coronavir Inhibitor pIC50 no unit 6.6 3-yl]propan-2- coronavirus C1=CC=CC2=CC=CC=C1 us 229E 2)NC(=O)OCC1=CC=C(O yl]carbamoyl}-2- 229E] CCCN2CCOCC2)C=C1 cyclohexylethyl]carbamoyl }-2-(naphthalen-1- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- NC(=O)[C@H](CC(C)C)N 3CL protease Coronavir 3.3E+07 3.3E+07 6.59 2-yl]carbamoyl}-3- C36H50N6O8 694.828 LLWOBJFCQNTMQC-AMEOFWRWSA-N3.769 2 0 Inhibitor pIC50 no unit 6.59 C(=O)[C@H](CC1=NC(O [Coronavirinae] inae C)=CC(C)=C1)NC(=O)OC methylbutyl]carbamoyl}-2- C1=CC=CC=C1 (6-methoxy-4- methylpyridin-2- yl)ethyl]carbamate

CSCC[C@H](NC(=O)[C@ H](CCC(O)=O)NC(=O)[C @H](CC1=CC=C(O)C=C1 )NC(=O)[C@@H](NC(=O )[C@H](CC(C)C)NC(=O)[ Middle C@H](CC(O)=O)NC(=O)[ spike protein East C@H](CC(C)C)NC(C)=O)[ C@@H](C)O)C(=O)N[C [Middle East respirator @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 6.59 C118H189N25O35S2550.01 XJXOKQDAPSDNJV-MXTOWPHFSA-N0.598 1 0 respiratory y Inhibitor EC50 muM 0.26 @@H](CO)C(=O)N[C@ syndrome syndrome @H](CC(C)C)C(=O)N[C@ @H](CCC(N)=O)C(=O)N[ coronavirus] coronavir C@@]1(C)CCCC=CCCC[C us @](C)(NC(=O)[C@H](CC CCN)NC(=O)[C@@H](N C(=O)[C@@H](NC1=O)C (C)C)C(C)C)C(=O)N[C@ 3C-like proteinase (cleavage SARS ClC1=CN=CC(OC(=O)C2 product of 1.1E+07 1.1E+07 6.57 C9H5ClN2O2S 240.67 CSEAAOWXHPFATP-UHFFFAOYSA-N1.798 4 2 coronavir IC50 nM 270 =CSC=N2)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase COC1=CC=C(OCC(=O)N[ (cleavage C@@H](C(C)C)C(=O)N[C SARS @@H](CC(C)C)C(=O)N[C product of 2.5E+07 2.5E+07 6.57 C36H45N5O7S691.849 WEJYZSSFVCVPIQ-GGCIBVLUSA-N3.45 3 0 coronavir Ki (inhibitionmuM constant) 0.27 @@H](C[C@@H]2CCNC Replicase 2=O)C(=O)C2=NC=C(S2) us C2=CC=CC=C2)C=C1 polyprotein 1ab) [SARS coronavirus]

[Na+].OC([C@H](C[C@ @H]1CCNC1=O)NC(=O)[ 3C-like protease Coronavir C@H](CC1CCCCC1)NC(= 3.2E+07 3.2E+07 6.54 C24H33ClN3O8S*Na582.05 QBZITZQGIUHVSG-GAPUZUELSA-M2.314 2 0 Inhibitor IC50 muM 0.29 O)OCC1=CC(Cl)=CC=C1) [Coronavirinae] inae S([O-])(=O)=O

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage SARS @@H](NC(=O)[C@H](C) product of NC(=O)OCC1=CC=CC=C 1.9E+07 1.9E+07 6.54 1034140-83-4 C32H41F3N4O6634.696 PDLFIYNGGUUVLF-GLMUFQRRSA-N5.092 2 0 coronavir Radioligand (/ligand)Binding affinityKi (inhibition of the compoundmuM constant) towards= SARS-CoV 3C-like0.29 protease in 20 mM Bis-Tris buffer, pH 7.0 at 25 degree C for 4 h Replicase 1)C(C)C)C(=O)NC(CC1=C us C=CC=C1)C(=O)C(F)(F)F polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS Benzyloxycarbonyl- product of No Structure 2.5E+07 2.5E+07 6.54 coronavir Ki (inhibitionmuM constant) 0.29 AVLF(D/L)-Trifluoromethyl Replicase us polyprotein 1ab) [SARS coronavirus]

Phenylmercuric nitrate; phenylmercury (1+); nitrate; Phenylquecksilber(1+); Sars Cov 3C-Like SARS O=N(=O)O[Hg]C1=CC=C 3770377 3770377 6.52 55-68-5 C6H5HgNO3 339.701 PDTFCHSETJBPTR-UHFFFAOYSA-N2.466 4 2 Radioligand (/ligand)Binding affinityKi (inhibition of the compoundmuM constant) towards= SARS-CoV 3C-like0.3 protease C=C1 Nitrat; phenylmercury Protease [SARS coronavir nitrate; phenyl mercuric coronavirus] us nitrate; phenyl mercury nitrate; Phenylmercurinitrat

Phenylmercuric nitrate; 3C-like phenylmercury (1+); proteinase nitrate; (cleavage Phenylquecksilber(1+); SARS O=N(=O)O[Hg]C1=CC=C product of 3770377 3770377 6.52 55-68-5 Nitrat; phenylmercury C6H5HgNO3 339.701 PDTFCHSETJBPTR-UHFFFAOYSA-N2.466 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.3 protease from SARS-CoV C=C1 Replicase nitrate; phenyl mercuric us polyprotein 1ab) nitrate; phenyl mercury [SARS nitrate; coronavirus] Phenylmercurinitrat

3C-like proteinase 2-[(2,4-dichloro-5- (cleavage CC1=C(Cl)C=C(Cl)C(=C1) SARS S(=O)(=O)C1=C(C=C(C=C methylphenyl)sulfonyl]-1,3- product of 1.1E+07 1.1E+07 6.52 C14H7Cl2F3N2O6S459.187 INAZPZCJNPPHGV-UHFFFAOYSA-N5.175 3 2 coronavir IC50 muM 0.3 1N(=O)=O)C(F)(F)F)N(=O dinitro-5- Replicase )=O us (trifluoromethyl)benzene polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage CN(C)C1=CC=C(C=C1)C( SARS =O)NC(CC1=CC=CC=C1) product of 2.5E+07 2.5E+07 6.52 C24H23ClN4O4466.924 NBBWJEWPUKPHPZ-UHFFFAOYSA-N4.859 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.3 protease from SARS-CoV C(=O)NC1=CC=C(C=C1Cl Replicase )N(=O)=O us polyprotein 1ab) [SARS coronavirus]

sodium (2S)-2-{(S)-2-[({[1- Middle (tert- 3C-like protease East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- [Middle East respirator =O)OC1CCN(CC1)C(=O) 4-yl]oxy} carbonyl)amino]- OC(C)(C)C)C(=O)N[C@@ 3.2E+07 3.2E+07 6.52 C24H41N4O10S*Na600.666 MVNGOUPOTIVRRK-FCSMXUNPSA-M0.271 2 0 respiratory y Inhibitor IC50 muM 0.3 4-methylpentanamido}-1- H](C[C@@H]1CCNC1=O syndrome syndrome )C(O)S([O-])(=O)=O hydroxy-3-[(S)-2- coronavirus] coronavir oxopyrrolidin-3-yl]propane- us 1-sulfonate

Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C [Middle East respirator )NC(=O)OC2CCC(CC2)C2 3.3E+07 3.3E+07 6.52 C26H38N3O8S*Na575.659 OOMCVQYVJKFVMJ-NEEZWBNRSA-M1.823 2 0 respiratory y Inhibitor EC50 muM 0.3 =CC=CC=C2)C(O)S([O- syndrome syndrome ])(=O)=O)CCNC1=O coronavirus] coronavir us Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ [Middle East respirator H](NC(=O)[C@H](CC(C)C 3.3E+07 3.3E+07 6.52 C20H36N3O8S*Na501.577 PNIWTLYNBHGOTC-XZKYERAWSA-M1.103 2 0 Inhibitor EC50 muM 0.3 )NC(=O)OCCCCCC)C(O)S respiratory y ([O-])(=O)=O)CCNC1=O syndrome syndrome coronavirus] coronavir us

(S)-benzyl (4-chloro-3-oxo- 1-phenylbutan-2- yl)carbamate; (S)-(1-benzyl- 3C-like 3-chloro-2- proteinase oxopropyl)carbamic acid (cleavage SARS [H][C@@](CC1=CC=CC= benzyl ester; (3S)-1-chloro- product of C1)(NC(=O)OCC1=CC=C 4264876 4264876 6.51 26049-94-5 C18H18ClNO3331.799 OYHLRJGDELITAF-INIZCTEOSA-N3.446 4 2 coronavir Ki (inhibitionnM constant) 306 2-oxo-3-N- Replicase C=C1)C(=O)CCl us benzyloxycarbonylamino-4- polyprotein 1ab) phenylbutane; N- [SARS carbobenzyloxy-L- coronavirus] phenylalanyl chloromethyl ketone; (3S)-3-

1-[(R)-1-(1-naphthyl)ethyl]- C[C@@H](N1CCC(CC1)C 4-[3,4- Papain-like SARS (=O)NCC1=CC2=C(OCO2 2.1E+07 2.1E+07 6.49 1234195-91-5 C26H28N2O3 416.52 IVXBCFLWMPMSAP-GOSISDBHSA-N4.47 4 2 IC50 muM 0.32 )C=C1)C1=C2C=CC=CC2 (methylenedioxy)benzylam protease [SARS coronavir =CC=C1 ino]carbonylpiperidine; coronavirus] us GRL-0667S

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- NC(=O)[C@H](CC(C)C)N 3CL protease Coronavir 3.3E+07 3.3E+07 6.49 2-yl]carbamoyl}-3- C33H43F3N6O7S724.802 SQARSOUMWKXROA-ZJZGAYNASA-N3.306 2 0 Inhibitor pIC50 no unit 6.49 C(=O)[C@H](CC1=NC(=C [Coronavirinae] inae S1)C(F)(F)F)NC(=O)OCC1 methylbutyl]carbamoyl}-2- =CC=CC=C1 [4-(trifluoromethyl)-1,3- thiazol-2- yl]ethyl]carbamate

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=C(C product of =CC=C2)N(=O)=O)=CN= 1.6E+07 1.6E+07 6.48 1007552-05-7 C12H7ClN2O4278.652 BWJAVTAYGYCMFB-UHFFFAOYSA-N2.786 4 2 coronavir IC50 nM 333 Replicase C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS (=CC=C1)N(C)C)C(C)C)C( product of 2.5E+07 2.5E+07 6.48 C32H46N6O6S 642.82 CEZLCCHFGRIUBL-DJESZUOASA-N2.03 2 0 coronavir Ki (inhibitionmuM constant) 0.33 =O)N[C@@H](C[C@@H Replicase ]1CCNC1=O)C(=O)C1=N us C=C(C)S1 polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- NC(=O)[C@H](CC(C)C)N 3CL protease Coronavir 3.3E+07 3.3E+07 6.48 2-yl]carbamoyl}-3- C35H48N6O7S696.868 JOVXDSIHEMZZIU-MNUOIFNESA-N2.266 2 0 Inhibitor pIC50 no unit 6.48 C(=O)[C@H](CC1=NC2= [Coronavirinae] inae C(CCC2)S1)NC(=O)OCC1 methylbutyl]carbamoyl}-2- =CC=CC=C1 {4H,5H,6H- cyclopenta[d][1,3]thiazol-2- yl}ethyl]carbamate

1-[(R)-1-(1-naphthyl)ethyl]- COC1=CC=C(CNC(=O)C2 Papain-like SARS CCN(CC2)[C@H](C)C2=C 4-(4- 2.1E+07 2.1E+07 6.47 1233939-86-0 C26H30N2O2 402.536 NTMTVRCCLOAJST-LJQANCHMSA-N4.896 4 2 protease [SARS coronavir IC50 muM 0.34 C=CC3=C2C=CC=C3)C=C methoxybenzylamino)carb 1 coronavirus] us onylpiperidine 1-[(R)-1-(1-naphthyl)ethyl]- COC1=CC(CNC(=O)C2CC Papain-like SARS N(CC2)[C@H](C)C2=CC= 4-(3- 2.1E+07 2.1E+07 6.47 1233939-85-9 C26H30N2O2 402.536 QKYBTDRNPVPOGN-LJQANCHMSA-N4.896 4 2 protease [SARS coronavir IC50 muM 0.34 CC3=C2C=CC=C3)=CC=C methoxybenzylamino)carb 1 coronavirus] us onylpiperidine

3C-like proteinase (cleavage SARS COC1=CC(=CC=C1)C(=O) product of 1.1E+07 1.1E+07 6.47 C13H10ClNO3 263.68 UIXQHURPUVBNCZ-UHFFFAOYSA-N2.809 4 2 coronavir IC50 nM 340 OC1=CC(Cl)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

(R)-N-((2-methoxypyridin-4- COC1=NC=CC(CNC(=O)C yl)methyl)-1-(1- Papain-like SARS 2CCN(CC2)[C@H](C)C2= 2.7E+07 2.7E+07 6.46 1581755-52-3 C25H29N3O2 403.524 MMIABLSMKGWQKD-GOSISDBHSA-N4.372 4 2 IC50 muM 0.35 CC=CC3=CC=CC=C23)=C (naphthalen-1- protease [SARS coronavir 1 yl)ethyl)piperidine-4- coronavirus] us carboxamide

3C-like proteinase (cleavage SARS NC(=O)C1=CC=C2N(CC3 product of =CC4=C(C=CC=C4)C=C3) 7597721 7597721 6.43 C20H14N2O3 330.343 NTNYHMJYSGPGCQ-UHFFFAOYSA-N2.59 4 2 coronavir IC50 muM 0.37 Replicase C(=O)C(=O)C2=C1 us polyprotein 1ab) [SARS coronavirus]

Severe Acute

NC(=O)C1=CC=C2N(CC3 Respiratory SARS =CC4=C(C=CC=C4)C=C3) 7597721 7597721 6.43 C20H14N2O3 330.343 NTNYHMJYSGPGCQ-UHFFFAOYSA-N2.59 4 2 Syndrome-Cov coronavir Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS0.37 CORONAVIRUS 3CL PROTEASE (0.5 uM) expressed in Escherichia coli BL21 (DE3) cells using 16 uM AVLQSGFRKK as substrate upon incubation in 50 mM Tris-HCl, pH 7.3 at 37 degree C by FLUORESCENCE RESONANCE ENERGY TRANSFER (FRET) ASSAY C(=O)C(=O)C2=C1 3Clpro [SARS us coronavirus]

3C-like proteinase (cleavage benzyl [3-chloro-1(S)-[(2- SARS ClCC(=O)[C@H](CC1=CC product of 2=CC=CC=C2C=C1)NC(= 1.2E+07 1.2E+07 6.43 naphthyl)methyl]-2- C22H20ClNO3381.859 BMGGQIBPEMUTCE-FQEVSTJZSA-N4.712 4 2 coronavir Ki (inhibitionnM constant) 371 Replicase O)OCC1=CC=CC=C1 oxopropyl] carbamate us polyprotein 1ab) [SARS coronavirus]

3C-like (3S)-3- proteinase benzyloxycarbonylamino-1- (cleavage chloro-4-(p-fluorophenyl)- SARS FC1=CC=C(C[C@H](NC(= product of O)OCC2=CC=CC=C2)C(= 9935262 9935262 6.42 400771-48-4 2-butanone; [N- C18H17ClFNO3349.789 SSXSAFSLNOWRIX-INIZCTEOSA-N3.607 4 2 coronavir Ki (inhibitionnM constant) 380 Replicase O)CCl)C=C1 (benzyloxycarbonyl)-3-(4- us polyprotein 1ab) fluorophenyl)-DL- [SARS alanyl]methyl chloride coronavirus]

(R)-N-(3-acetamidobenzyl)- C[C@@H](N1CCC(CC1)C Papain-like SARS (=O)NCC1=CC(NC(C)=O) 1-(1-(naphthalen-1- 2.7E+07 2.7E+07 6.41 1581755-39-6 C27H31N3O2 429.562 YQRGVYYHRJBSOR-LJQANCHMSA-N4.235 4 2 protease [SARS coronavir IC50 muM 0.39 =CC=C1)C1=CC=CC2=CC yl)ethyl)-piperidine-4- =CC=C12 coronavirus] us carboxamide

(S)-3- benzyloxycarbonylamino-5- bromo-4-oxo-pentanoic 3C-like acid tert-butyl ester; (3S)-3- proteinase (N- (cleavage SARS CC(C)(C)OC(=O)C[C@H]( benzyloxycarbonyl)amino- product of NC(=O)OCC1=CC=CC=C 6820432 6820432 6.4 153088-76-7 C17H22BrNO5400.269 PBVFTOAYKLEQQO-ZDUSSCGKSA-N3.077 4 1 coronavir Ki (inhibitionnM constant) 400 5-bromo-4-oxopentanoic Replicase 1)C(=O)CBr us acid tert-butyl ester; (S)-3- polyprotein 1ab) benzyloxycarbonylamino-5- [SARS bromo-4-oxopentanoic coronavirus] acid tert-butyl ester; (S)- tert-butyl 3-

sodium (2S)-2-{(S)-2-[({[1- Middle (tert- Replicase East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- polyprotein 1ab respirator =O)OC1CCN(CC1)C(=O) 4-yl]oxy} carbonyl)amino]- [Middle East OC(C)(C)C)C(=O)N[C@@ 3.2E+07 3.2E+07 6.4 C24H41N4O10S*Na600.666 MVNGOUPOTIVRRK-FCSMXUNPSA-M0.271 2 0 y Inhibitor IC50 muM 0.4 4-methylpentanamido}-1- respiratory H](C[C@@H]1CCNC1=O syndrome )C(O)S([O-])(=O)=O hydroxy-3-[(S)-2- syndrome coronavir oxopyrrolidin-3-yl]propane- coronavirus] us 1-sulfonate benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- NC(=O)[C@H](CC(C)C)N 3CL protease Coronavir 3.3E+07 3.3E+07 6.4 2-yl]carbamoyl}-3- C35H45F3N6O8734.773 BRFLNKODYPAWQW-MNUOIFNESA-N4.584 2 0 Inhibitor pIC50 no unit 6.4 C(=O)[C@H](CC1=NC(O [Coronavirinae] inae C(F)(F)F)=CC=C1)NC(=O) methylbutyl]carbamoyl}-2- OCC1=CC=CC=C1 [6- (trifluoromethoxy)pyridin- 2-yl]ethyl]carbamate

[Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C 3C-like protease Coronavir )NC(=O)OCC2=CC(Cl)=C 3.3E+07 3.3E+07 6.4 C21H29ClN3O8S*Na541.985 QERRPHDKVCOWJG-OPOLGWMESA-M0.947 2 0 Inhibitor EC50 muM 0.4 C=C2)C(O)S([O- [Coronavirinae] inae ])(=O)=O)CCNC1=O

[Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C 3C-like protease Coronavir )NC(=O)OC2CCC(CC2)C2 3.3E+07 3.3E+07 6.4 C26H38N3O8S*Na575.659 OOMCVQYVJKFVMJ-NEEZWBNRSA-M1.823 2 0 Inhibitor EC50 muM 0.4 =CC=CC=C2)C(O)S([O- [Coronavirinae] inae ])(=O)=O)CCNC1=O

[Na+].OC([C@H](C[C@ @H]1CCNC1=O)NC(=O)[ 3C-like protease Coronavir C@H](CC1CCCCC1)NC(= 3.2E+07 3.2E+07 6.38 C24H34N3O8S*Na547.605 QIIXTKHVLHZPQZ-SJZJPLIYSA-M1.692 2 0 Inhibitor IC50 muM 0.42 O)OCC1=CC=CC=C1)S([ [Coronavirinae] inae O-])(=O)=O

3C-like proteinase (cleavage SARS ClC1=CC=C(C=C1)C(=O) product of 1.6E+07 1.6E+07 6.36 1007552-04-6 C12H7Cl2NO2268.099 KLXHMZDATSPDMW-UHFFFAOYSA-N3.516 4 2 coronavir IC50 nM 434 OC1=CN=CC(Cl)=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC(OC(F)(F)F) 1-[(propan-2- =CC=C1)NC(=O)OCC1=C 3CL protease Coronavir 3.3E+07 3.3E+07 6.36 yl)carbamoyl]propan-2- C34H43F3N6O8720.746 SDGSGHDLEGVDQD-GKXKVECMSA-N4.117 2 0 Inhibitor pIC50 no unit 6.36 C=CC=C1)C(=O)N[C@@ [Coronavirinae] inae H](C[C@@H]1CCNC1=O yl]carbamoyl}butyl]carbam )C(=O)C(=O)NC(C)C oyl}-2-[6- (trifluoromethoxy)pyridin- 2-yl]ethyl]carbamate

C[C@@H](NC(=O)C1=C( 5-methylamino-2-methyl- Papain-like SARS C)C=CC(CN)=C1)C1=CC= 2E+07 2E+07 6.34 1184301-69-6N-[(R)-1-(1- C21H22N2O 318.418 BIKTWHWUIKAJAT-OAHLLOKOSA-N4.488 4 2 protease [SARS coronavir IC50 muM 0.46 CC2=CC=CC=C12 naphthyl)ethyl]benzamide coronavirus] us

3C-like

COC1=CC=C(OCC(=O)N[ proteinase C@@H](C(C)C)C(=O)N[C (cleavage SARS @@H](CC(C)C)C(=O)N[C product of @@H](C[C@@H]2CCNC 2.5E+07 2.5E+07 6.33 C37H47N5O8S721.875 BWUPIUXLXYQDPH-IHAGIBJBSA-N3.365 3 0 coronavir Ki (inhibitionmuM constant) 0.47 Replicase 2=O)C(=O)C2=NC=C(S2) us C2=C(OC)C=CC=C2)C=C polyprotein 1ab) 1 [SARS coronavirus]

CCC1=CC=C(CNC(=O)C2 (R)-N-(4-ethylbenzyl)-1-(1- Papain-like SARS CCN(CC2)[C@H](C)C2=C 2.7E+07 2.7E+07 6.33 1581755-35-2 C27H32N2O 400.564 XPZZHYRWRVPSGO-HXUWFJFHSA-N5.882 3 2 IC50 muM 0.47 C=CC3=C2C=CC=C3)C=C (naphthalen-1-yl)ethyl)- protease [SARS coronavir 1 piperidine-4-carboxamide coronavirus] us

benzyl N-[(2S)-1- [(1S,3aR,6aS)-1-{[(2S)-1- [H][C@@]12CCC[C@]1([ oxo-3-[(3S)-2-oxopyrrolidin- H])[C@H](N(C2)C(=O)[C 3-yl]-1-[(propan-2- @H](CC1=CC=C(F)C=C1) 3CL protease Coronavir NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 6.33 yl)carbamoyl]propan-2- C36H44FN5O7677.773 GCSPVCXSCCUGET-HBESODNUSA-N3.159 2 0 Inhibitor pIC50 no unit 6.33 [Coronavirinae] inae 1)C(=O)N[C@@H](C[C@ yl]carbamoyl}octahydrocyc @H]1CCNC1=O)C(=O)C( =O)NC(C)C lopenta[c]pyrrol-2-yl]-3-(4- fluorophenyl)-1-oxopropan- 2-yl]carbamate

5-amino-2-methyl-N-[(R)-1- (1- Papain-like C[C@@H](NC(=O)C1=C( naphthyl)ethyl]benzamide; Coronavir C)C=CC(N)=C1)C1=C2C= 2E+07 2E+07 6.31 1093070-16-6 C20H20N2O 304.392 UVERBUNNCOKGNZ-CQSZACIVSA-N4.549 4 2 protease BiodistributionKi (inhibition of ~ 0.63muM MBqconstant) compound= in KIDNEY TISSUE0.49 at 24 hour in NCr nude mouse bearing LNCaP xenografts GRL-0617S; 5-Amino-2- idae CC=CC2=CC=C1 [Coronaviridae] methyl-N-[(R)-1-(1- naphthyl)ethyl]benzamide

C[C@@H](N1CCC(CC1)C (R)-N-(4-fluorobenzyl)-1-(1- Papain-like SARS (=O)NCC1=CC=C(F)C=C1 2.7E+07 2.7E+07 6.31 1581755-44-3 C25H27FN2O 390.501 VTAUBQMDNJOEAK-GOSISDBHSA-N5.142 3 2 IC50 muM 0.49 )C1=CC=CC2=CC=CC=C1 (naphthalen-1-yl)ethyl)- protease [SARS coronavir 2 piperidine-4-carboxamide coronavirus] us 3C-like mercury ion; Mercury; proteinase mercury(II) chloride; (cleavage SARS mercury(II) cation; product of [Hg] 3587187 3587187 6.3 Hg 200.59 QSHDDOUJBYECFT-UHFFFAOYSA-N0 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.5 protease from SARS-CoV mercury(II) ion; Replicase us mercury(II)(2+); polyprotein 1ab) mercury(II)-ion [SARS coronavirus] Severe Acute Respiratory ClC1=CC(OC(=O)C2=CC= Coronavir 1.9E+07 1.9E+07 6.3 219929-01-8 C10H6ClNO2S 239.682 PAVJYVVZIJTAHT-UHFFFAOYSA-N1.956 4 2 Syndrome-Cov Inhibitor Inhibitory concentrationIC50 muM of the compound= against Severe0.5 acute respiratory syndrome-CoV 3CLpro using 2-aminobenzoyl-SVTLQSG-Tyr(NO2)-R as substrate in 100 mM potassium phosphate, pH 8.0 by FRET assay CS2)=CN=C1 idae 3Clpro [Coronaviridae] Sars Cov 3C-Like SARS ClC1=CC(OC(=O)C2=CC= 1.9E+07 1.9E+07 6.3 219929-01-8 C10H6ClNO2S 239.682 PAVJYVVZIJTAHT-UHFFFAOYSA-N1.956 4 2 Inhibitor Inhibitory concentrationIC50 muM against SARS-CoV= 3C-like protease0.5 with 2-aminobenzoyl-SVTLQSG-Tyr(NO2)-R as substrate in 100 mM potassium phosphate buffer, pH 8 done at RT using fluorescence resonance energy transfer assay CS2)=CN=C1 Protease [SARS coronavir coronavirus] us

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of 1.9E+07 1.9E+07 6.3 219929-01-8 C10H6ClNO2S 239.682 PAVJYVVZIJTAHT-UHFFFAOYSA-N1.956 4 2 coronavir Inhibitor In vitro inhibitoryIC50 concentrationmuM of the= compound against0.5 3C-like protease from SARS-CoV CS2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC= product of C(O2)C2=CC(=CC=C2)N( 1.6E+07 1.6E+07 6.3 1007552-01-3 C16H9ClN2O5344.711 FFZBRNPLWVOTBP-UHFFFAOYSA-N3.439 4 2 coronavir IC50 nM 500 Replicase =O)=O)=CN=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CCOC(=O)\C=C\C(CC1=C (cleavage SARS C=CC=C1)NC(=O)[C@H]( product of CC1=CC=CC=C1)NC(=O) 2.6E+07 2.6E+07 6.3 C33H37N3O4 539.674 JWPLKCWYGMPRGX-OZJPHXNQSA-N5.753 2 1 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.5 protease from SARS-CoV Replicase \C=C\C1=CC=C(C=C1)N( us C)C polyprotein 1ab) [SARS coronavirus]

Severe Acute Respiratory SARS BrC1=CC(OC(=O)C2=CC= 2.6E+07 2.6E+07 6.3 C10H6BrNO2S284.133 DBZLJJMKJAMBRF-UHFFFAOYSA-N2.132 4 2 Inhibitory concentrationIC50 muM of compound (dissolved in DMSO)0.5 against 3CL Protease from Severe Acute Respiratory Syndrome Coronavirus expressed in Escherichia coli BL21(DE3) upon incubation in 50 mM HEPES, pH 7.5 for 30 minutes at RT CS2)=CN=C1 Syndrome-Cov coronavir 3Clpro [SARS us coronavirus]

Severe Acute Respiratory SARS BrC1=CC(OC(=O)C2=CC= 2.6E+07 2.6E+07 6.3 C10H6BrNO2S284.133 DBZLJJMKJAMBRF-UHFFFAOYSA-N2.132 4 2 Inhibitor Inhibitory concentrationIC50 muM of compound= against SEVERE ACUTE0.5 RESPIRATORY SYNDROME CORONAVIRUS 3CL PROTEASE (1 uM) using 100 uM ABZ-SVTLQSG-TYR(NO2)R as substrate upon incubation in 100 mM potassium phosphate, pH 8.0 at RT by FRET assay CS2)=CN=C1 Syndrome-Cov coronavir 3Clpro [SARS us coronavirus]

sodium (2S)-1-hydroxy-2- Middle {(S)-4-methyl-2-[({[1- 3C-like protease East [Na+].CC(C)C[C@H](NC( (methylsulfonyl)piperidin- [Middle East respirator =O)OC1CCN(CC1)S(C)(= 4- O)=O)C(=O)N[C@@H](C 3.2E+07 3.2E+07 6.3 C20H35N4O10S2*Na578.64 OXYUFTIDAUNJGP-KEWDJMNSSA-M-1.395 2 0 respiratory y Inhibitor IC50 muM 0.5 yl]oxy}carbonyl)amino]pen [C@@H]1CCNC1=O)C(O syndrome syndrome )S([O-])(=O)=O tanamido}-3-[(S)-2- coronavirus] coronavir oxopyrrolidin-3-yl]propane- us 1-sulfonate

[Bi+3].[O- ]N(=O)=O.COC1=CC(=CC (OC)=C1OC)C1=C2[N- ]C(\C=C/2)=C(/C2=N/C(/ SARS C=C2)=C(\C2=CC=C([N- helicase [SARS 1.6E+07 1.6E+07 6.3 Bi*C56H52N4O12*NO31244.03 GUVHQKNLOYUAJE-FROCSNILSA-N1 0 coronavir Effect : enzyme;IC50 inhib. ofmuM Bioassay : control: DMSO; AM/MG:0.5 malachite green and molybdate test-system (0.2-0.7 pmol) incub. with 1 mM ATP for 10 min at 25 deg C; reaction stopped by adding 0.5 M EDTA; AM/MG reagent added followed by trisodium citrate; absorbance at 630 nm reported; ATPase activity determ. ]2)/C(=C2/C=CC\1=N/2) coronavirus] C1=CC(OC)=C(OC)C(OC) us =C1)C1=CC(OC)=C(OC)C (OC)=C1)C1=CC(OC)=C( OC)C(OC)=C1

3C-like proteinase (cleavage SARS ClC1=CC(CC(=O)C2=CC= product of 2.6E+07 2.6E+07 6.3 1222829-75-5 C11H8ClNOS 237.71 HKMXTOFQPPXPPD-UHFFFAOYSA-N1.86 4 2 coronavir Inhibitor In vitro inhibitoryIC50 concentrationmuM of the= compound against0.5 SARS-CoV main protease CS2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

sodium (2S)-2-{(S)-2-[({[1- Middle Replicase (ethoxycarbonyl)piperidin- East [Na+].CCOC(=O)N1CCC( polyprotein 1ab 4-yl]oxy}carbonyl)amino]-4- respirator CC1)OC(=O)N[C@@H](C [Middle East C(C)C)C(=O)N[C@@H](C 3.2E+07 3.2E+07 6.3 methylpentanamido}-1- C22H37N4O10S*Na572.612 FTLUCMWMNGOWPX-OPOLGWMESA-M-0.606 2 0 y Inhibitor IC50 muM 0.5 respiratory [C@@H]1CCNC1=O)C(O hydroxy-3-[(S)-2- syndrome )S([O-])(=O)=O syndrome oxopyrrolidin-3-yl]propane- coronavir coronavirus] 1-sulfonate us Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C [Middle East respirator )NC(=O)OCCC2=CC=CC( 3.3E+07 3.3E+07 6.3 C22H31ClN3O8S*Na556.012 ZIVZAVLWWUPQGT-FCSMXUNPSA-M1.105 2 0 respiratory y Inhibitor EC50 muM 0.5 Cl)=C2)C(O)S([O- syndrome syndrome ])(=O)=O)CCNC1=O coronavirus] coronavir us

[Na+].[H][C@@]1(C[C@ 3C-like protease Coronavir H](NC(=O)[C@H](CC(C)C 3.3E+07 3.3E+07 6.3 C20H36N3O8S*Na501.577 PNIWTLYNBHGOTC-XZKYERAWSA-M1.103 2 0 Inhibitor EC50 muM 0.5 )NC(=O)OCCCCCC)C(O)S [Coronavirinae] inae ([O-])(=O)=O)CCNC1=O

COC(=O)C[C@H](NC(=O SARS )[C@@H](NC(=O)OCC1= Protease [SARS 2.5E+07 2.5E+07 6.29 C19H25FN2O6396.416 coronavir Inhibitor Equilibrium Kiinhibition (inhibition constantnM constant) of compound= against recombinant512 SARS coronavirus (SARS-CoV) Protease 3CLpro expressed in E. coli BL21 Star DE3 cells incubated using Dabcyl-Lys-Thr-Ser-Ala-Val-Leu-Gln-Ser-Gly-Phe-Arg-Lys-Met-Gln-Edans substrate at 25 degree C in 10 mM sodium phosphate, pH 7.4 CC=CC=C1)C(C)C)C(=O)C coronavirus] F us

3C-like proteinase benzyloxycarbonyl-L-Val- (cleavage DL-Asp(OMe)- SARS COC(=O)CC(NC(=O)[C@ product of @H](NC(=O)OCC1=CC= 9654802 9654802 6.29 fluoromethylketone; Z-Val- C19H25FN2O6396.416 DPHACENAZHGWHS-JRZJBTRGSA-N1.655 4 1 coronavir Ki (inhibitionnM constant) 512 Replicase CC=C1)C(C)C)C(=O)CF DL-Asp(OMe)- us polyprotein 1ab) fluoromethylketone [SARS coronavirus]

2-((4- Main proteinase SARS ClC1=CC=C(SSC2=NN=C 3.1E+07 3.1E+07 6.29 C8H5ClN2OS2 244.725 YANPJRMMERZAJG-UHFFFAOYSA-N4.021 4 2 Inhibitor IC50 muM 0.516 O2)C=C1 chlorophenyl)disulfanyl)- (Mpro) [SARS coronavir 1,3,4-oxadiazole coronavirus] us

3C-like proteinase CCOC(=O)\C=C\[C@H](C (cleavage SARS C1=CC=CC=C1)NC(=O)[C product of @H](CC1=CC=CC=C1)NC 1.1E+07 1.1E+07 6.28 C33H37N3O4 539.674 JWPLKCWYGMPRGX-ZIIPDIQWSA-N5.753 2 1 coronavir Ki (inhibitionmuM constant) 0.52 Replicase (=O)\C=C\C1=CC=C(C=C us 1)N(C)C polyprotein 1ab) [SARS coronavirus]

Severe Acute CCOC(=O)\C=C\[C@H](C C1=CC=CC=C1)NC(=O)[C Respiratory SARS @H](CC1=CC=CC=C1)NC 1.1E+07 1.1E+07 6.28 C33H37N3O4 539.674 JWPLKCWYGMPRGX-ZIIPDIQWSA-N5.753 2 1 Syndrome-Cov coronavir Radioligand (/ligand)Inhibition constantKi (inhibition againstmuM constant) Severe acute respiratory syndrome-Corona0.52 virus 3C-like protein (SARS-CoV 3CLpro) was determined (=O)\C=C\C1=CC=C(C=C 3Clpro [SARS us 1)N(C)C coronavirus]

CCOC(=O)\C=C\C(CC1=C C=CC=C1)NC(=O)[C@H]( Sars Cov 3C-Like SARS CC1=CC=CC=C1)NC(=O) 2.6E+07 2.6E+07 6.28 C33H37N3O4 539.674 JWPLKCWYGMPRGX-OZJPHXNQSA-N5.753 2 1 Protease [SARS coronavir Radioligand (/ligand)Binding affinityKi (inhibition of the compoundmuM constant) towards= SARS-CoV 3C-like0.52 protease (50 nM) using 6 uM fluorogenic substrate \C=C\C1=CC=C(C=C1)N( coronavirus] us C)C

SARS CC1=NC(I)=C(C(O)=O)C( helicase [SARS =C1O)[C@@]12OC3(O)C 2.5E+07 2.5E+07 6.27 C14H14INO9 467.171 HCDBOXMXKHRPSB-UDAZWBJDSA-N-0.336 4 1 coronavir Inhibitor Inhibition ofIC50 ATPase activitymuM of SARS= coronavirus helicase0.54 coronavirus] C(O)(CC(O)(C3)O1)O2 us

5-amino-2-methyl-N-[(R)-1- (1- Papain-like SARS C[C@@H](NC(=O)C1=C( naphthyl)ethyl]benzamide; C)C=CC(N)=C1)C1=C2C= 2E+07 2E+07 6.25 1093070-16-6 C20H20N2O 304.392 UVERBUNNCOKGNZ-CQSZACIVSA-N4.549 4 2 protease [SARS coronavir IC50 muM 0.56 GRL-0617S; 5-Amino-2- CC=CC2=CC=C1 coronavirus] us methyl-N-[(R)-1-(1- naphthyl)ethyl]benzamide 1-[(S)-1-(1-naphthyl)ethyl]- C[C@H](N1CCC(CC1)C(= 4-[3,4- Papain-like SARS O)NCC1=CC2=C(OCO2)C 2.1E+07 2.1E+07 6.25 1233939-90-6 C26H28N2O3 416.52 IVXBCFLWMPMSAP-SFHVURJKSA-N4.47 4 2 IC50 muM 0.56 =C1)C1=C2C=CC=CC2=C (methylenedioxy)benzylam protease [SARS coronavir C=C1 ino]carbonylpiperidine; coronavirus] us GRL-0737S

1-[(S)-1-(1-naphthyl)ethyl]- C[C@H](N1CCC(CC1)C(= 4-[3,4- Papain-like SARS O)NCC1=CC2=C(OCO2)C 2.1E+07 2.1E+07 6.25 1233939-90-6 C26H28N2O3 416.52 IVXBCFLWMPMSAP-SFHVURJKSA-N4.47 4 2 Inhibitor Inhibitory concentrationIC50 muM of compound= against SARS coronavirus0.56 papain-like protease expressed in Escherichia coliBL21(DE3) using 50 uM RLRGG-AMC as substrate upon incubation at 25 degree C =C1)C1=C2C=CC=CC2=C (methylenedioxy)benzylam protease [SARS coronavir C=C1 ino]carbonylpiperidine; coronavirus] us GRL-0737S

Papain-like C[C@@H](NC(=O)C1=C( Coronavir C)C=CC=C1NC(C)=O)C1= 2.5E+07 2.5E+07 6.25 C22H22N2O2 346.429 OQBMJEFDHAVIAH-OAHLLOKOSA-N5.049 3 2 protease Inhibitor Inhibitory concentrationIC50 muM of the compound= against coronavirus0.56 papain-like protease (125 nM) expressed in Escherichia coli upon incubation in 50 mM HEPES, pH 7.5 using fluorogeneic peptide RLRGGAMC substrate (50 uM) idae CC=CC2=CC=CC=C12 [Coronaviridae]

C[C@@H](N1CCC(CC1)C (R)-N-(4-chlorobenzyl)-1-(1- Papain-like SARS (=O)NCC1=CC=C(Cl)C=C 2.7E+07 2.7E+07 6.24 1581755-42-1 C25H27ClN2O406.955 WYSVTAFOGXZFNZ-GOSISDBHSA-N5.603 3 2 IC50 muM 0.58 1)C1=CC=CC2=CC=CC=C (naphthalen-1-yl)ethyl)- protease [SARS coronavir 12 piperidine-4-carboxamide coronavirus] us

[Na+].OC([C@H](C[C@ @H]1CCNC1=O)NC(=O)[ 3C-like protease Coronavir C@H](CC1CCCCC1)NC(= 3.2E+07 3.2E+07 6.23 C24H33ClN3O8S*Na582.05 QBZITZQGIUHVSG-GAPUZUELSA-M2.314 2 0 Inhibitor IC50 muM 0.59 O)OCC1=CC(Cl)=CC=C1) [Coronavirinae] inae S([O-])(=O)=O

phenylmethyl-N-[(2S)-1- [[(2S)-1-[[(2S,3R,4R,5S)-3,4- dihydroxy-5-[[(2S)-3- CC(C)[C@H](NC(=O)[C@ methyl-2-[[(2S)-2- H](C)NC(=O)OCC1=CC=C Severe Acute C=C1)C(=O)N[C@@H](C (phenylmethoxycarbonyla Respiratory SARS C1=CC=CC=C1)[C@@H]( mino)propanoyl]amino]but O)[C@H](O)[C@H](CC1= 8250026 8250026 6.22 204907-85-7 C50H64N6O10909.092 BJJPNOGMLLUCER-KUTQPOQPSA-N5.54 0 0 Syndrome-Cov coronavir Radioligand (/ligand)Inhibition constantKi (inhibition againstmuM constant) Severe acute= respiratory syndrome-Corona0.6 virus 3C-like protein (SARS-CoV 3CLpro) was measured anoyl]amino]-1,6- CC=CC=C1)NC(=O)[C@ 3Clpro [SARS us @H](NC(=O)[C@H](C)N di(phenyl)hexan-2- C(=O)OCC1=CC=CC=C1) coronavirus] C(C)C yl]amino]-3-methyl-1- oxobutan-2-yl]amino]-1- oxopropan-2- yl]carbamate; TL3; TL-3 phenylmethyl-N-[(2S)-1- [[(2S)-1-[[(2S,3R,4R,5S)-3,4- dihydroxy-5-[[(2S)-3- 3C-like CC(C)[C@H](NC(=O)[C@ H](C)NC(=O)OCC1=CC=C methyl-2-[[(2S)-2- proteinase C=C1)C(=O)N[C@@H](C (phenylmethoxycarbonyla (cleavage SARS C1=CC=CC=C1)[C@@H]( mino)propanoyl]amino]but product of O)[C@H](O)[C@H](CC1= 8250026 8250026 6.22 204907-85-7 C50H64N6O10909.092 BJJPNOGMLLUCER-KUTQPOQPSA-N5.54 0 0 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.6 protease from SARS-CoV anoyl]amino]-1,6- Replicase CC=CC=C1)NC(=O)[C@ us @H](NC(=O)[C@H](C)N di(phenyl)hexan-2- polyprotein 1ab) C(=O)OCC1=CC=CC=C1) [SARS C(C)C yl]amino]-3-methyl-1- oxobutan-2-yl]amino]-1- coronavirus] oxopropan-2- yl]carbamate; TL3; TL-3

5-amino-2-methyl-N-[(R)-1- (1- Papain-like C[C@@H](NC(=O)C1=C( naphthyl)ethyl]benzamide; Coronavir C)C=CC(N)=C1)C1=C2C= 2E+07 2E+07 6.22 1093070-16-6 C20H20N2O 304.392 UVERBUNNCOKGNZ-CQSZACIVSA-N4.549 4 2 protease Minimum inhibitoryIC50 concentrationmuM of= the compound (dissolved0.6 in DMSO) against SALMONELLA TYPHI MTCC 98 upon incubation for overnight at 37 degree C GRL-0617S; 5-Amino-2- idae CC=CC2=CC=C1 [Coronaviridae] methyl-N-[(R)-1-(1- naphthyl)ethyl]benzamide

5-amino-2-methyl-N-[(R)-1- Severe Acute (1- Respiratory SARS C[C@@H](NC(=O)C1=C( naphthyl)ethyl]benzamide; C)C=CC(N)=C1)C1=C2C= 2E+07 2E+07 6.22 1093070-16-6 C20H20N2O 304.392 UVERBUNNCOKGNZ-CQSZACIVSA-N4.549 4 2 Syndrome-Cov coronavir Inhibitory concentrationIC50 nM of compound (dissolved in DMSO)600 against 3CL Protease from Severe Acute Respiratory Syndrome Coronavirus expressed in Escherichia coli BL21(DE3) upon incubation in 50 mM HEPES, pH 7.5 for 30 minutes at RT GRL-0617S; 5-Amino-2- CC=CC2=CC=C1 3Clpro [SARS us methyl-N-[(R)-1-(1- coronavirus] naphthyl)ethyl]benzamide

5-amino-2-methyl-N-[(R)-1- (1- Papain-like SARS C[C@@H](NC(=O)C1=C( naphthyl)ethyl]benzamide; C)C=CC(N)=C1)C1=C2C= 2E+07 2E+07 6.22 1093070-16-6 C20H20N2O 304.392 UVERBUNNCOKGNZ-CQSZACIVSA-N4.549 4 2 protease [SARS coronavir Inhibitor Inhibitory concentrationIC50 muM of compound= against SARS coronavirus0.6 papain-like protease expressed in Escherichia coliBL21(DE3) using 50 uM RLRGG-AMC as substrate upon incubation at 25 degree C GRL-0617S; 5-Amino-2- CC=CC2=CC=C1 coronavirus] us methyl-N-[(R)-1-(1- naphthyl)ethyl]benzamide

[H][C@@]1(C[C@H](NC( =O)[C@H](CC(C)C)NC(= Severe Acute O)[C@@H](NC(=O)[C@ Respiratory SARS @H](NC(C)=O)C(C)C)[C 9892814 9892814 6.22 C40H52N8O11 820.9 TYWILPQKGVLDRA-YIJKKHBBSA-N3.013 1 0 Inhibitor Inhibitory activityIC50 againstmuM Severe acute= respiratory syndrome-Corona0.6 virus 3C-like protein (SARS-CoV 3CLpro) was determined @@H](C)OCC2=CC=CC= Syndrome-Cov coronavir C2)C(=O)CN2NC(=O)C3= 3Clpro [SARS us C(C=CC=C3N(=O)=O)C2 coronavirus] =O)CCNC1=O [H][C@@]1(C[C@H](NC( =O)[C@H](CC(C)C)NC(= O)[C@@H](NC(=O)[C@ Sars Cov 3C-Like SARS @H](NC(C)=O)C(C)C)[C 9892814 9892814 6.22 C40H52N8O11 820.9 TYWILPQKGVLDRA-YIJKKHBBSA-N3.013 1 0 Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS-CoV0.6 3C-like protease @@H](C)OCC2=CC=CC= Protease [SARS coronavir C2)C(=O)CN2NC(=O)C3= coronavirus] us C(C=CC=C3N(=O)=O)C2 =O)CCNC1=O

sodium (2S)-2-{(S)-2-[({[4- Middle benzyl-1-(tert- 3C-like protease East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- =O)OC1(CC2=CC=CC=C2 [Middle East respirator )CCN(CC1)C(=O)OC(C)(C 4-yl]oxy}carbonyl)amino]-4- 3.2E+07 3.2E+07 6.22 C31H47N4O10S*Na690.791 GODLXHBNULFSDU-WYYMQYPJSA-M2.133 2 0 respiratory y Inhibitor IC50 muM 0.6 )C)C(=O)N[C@@H](C[C methylpentanamido}-1- @@H]1CCNC1=O)C(O)S syndrome syndrome hydroxy-3-[(S)-2- ([O-])(=O)=O coronavirus] coronavir oxopyrrolidin-3-yl]propane- us 1-sulfonate

sodium (2S)-1-hydroxy-2- Middle {(S)-4-methyl-2-[({[1- Replicase East [Na+].CC(C)C[C@H](NC( (methylsulfonyl)piperidin- polyprotein 1ab respirator =O)OC1CCN(CC1)S(C)(= 4- [Middle East O)=O)C(=O)N[C@@H](C 3.2E+07 3.2E+07 6.22 C20H35N4O10S2*Na578.64 OXYUFTIDAUNJGP-KEWDJMNSSA-M-1.395 2 0 y Inhibitor IC50 muM 0.6 yl]oxy}carbonyl)amino]pen respiratory [C@@H]1CCNC1=O)C(O syndrome )S([O-])(=O)=O tanamido}-3-[(S)-2- syndrome coronavir oxopyrrolidin-3-yl]propane- coronavirus] us 1-sulfonate

[Bi+3].[O-]N(=O)=O.[N- ]1C2=CC=C1\C(C1=CC=C SARS C=C1)=C1\C=CC(=N\1)/ helicase [SARS C(C1=CC=CC=C1)=C1[N- 1.6E+07 1.6E+07 6.22 Bi*C44H28N4*NO3883.718 ZUMUQSXKNNURNJ-YKKPBKTHSA-N2 2 coronavir Effect : enzyme;IC50 inhib. ofmuM Bioassay : control: DMSO; AM/MG:0.6 malachite green and molybdate test-system (0.2-0.7 pmol) incub. with 1 mM ATP for 10 min at 25 deg C; reaction stopped by adding 0.5 M EDTA; AM/MG reagent added followed by trisodium citrate; absorbance at 630 nm reported; ATPase activity determ. coronavirus] ]C(/C=C\1)=C(\C1=N\C(\ us C=C1)=C/2C1=CC=CC=C 1)C1=CC=CC=C1

3C-like proteinase Acetyl-VT(O-(Benzyl))LA(3- (cleavage ((S)-2-oxopyrrolidin-3-yl))- SARS product of No Structure 2.4E+07 2.4E+07 6.22 (1,4-dioxo-2,3-dihydro-5- coronavir IC50 muM 0.6 Replicase nitro-phthalazine-2- us polyprotein 1ab) yl)methyl [SARS coronavirus]

3C-like proteinase Acetyl-VS(O-(Benzyl))LA(3- (cleavage ((R)-2-oxo-3-pyrrolidyl))- SARS product of No Structure 2.5E+07 2.5E+07 6.22 (1,4-dioxo-2,3-dihydro-5- coronavir IC50 muM 0.6 Replicase nitro-phthalazine-2- us polyprotein 1ab) yl)methyl [SARS coronavirus]

3C-like CC(C)C[C@H](NC(=C)[C proteinase @@H](NC(=O)[C@@H]( (cleavage NC(C)=O)C(C)C)[C@@H] SARS (C)OCC1=CC=CC=C1)C(= product of 2.6E+07 2.6E+07 6.22 1350215-80-3 C41H54N8O10818.927 SJIZFTYKKAAHOM-SKPWYZPUSA-N4.094 1 0 coronavir Inhibitor In vitro inhibitoryIC50 concentrationmuM of the= compound against0.6 3C-like protease from SARS-CoV O)N[C@@H](CC1CCNC1 Replicase =O)C(=O)CN1NC(=O)C2 us =C(C=CC=C2N(=O)=O)C polyprotein 1ab) 1=O [SARS coronavirus]

(R)-N-(4- CNC(=O)C1=CC=C(CNC( (methylcarbamoyl)benzyl)- Papain-like SARS =O)C2CCN(CC2)[C@H](C 2.7E+07 2.7E+07 6.22 1581755-36-3 C27H31N3O2 429.562 CLOQJEWVRBXFRU-LJQANCHMSA-N4.386 4 2 IC50 muM 0.6 )C2=CC=CC3=CC=CC=C2 1-(1-(naphthalen-1-yl)- protease [SARS coronavir 3)C=C1 ethyl)piperidine-4- coronavirus] us carboxamide

Middle tert-butyl 4-({[(S)-4-methyl- Replicase East 1-oxo-1-({(S)-1-oxo-3-[(S)-2- polyprotein 1ab CC(C)C[C@H](NC(=O)OC respirator 1CCN(CC1)C(=O)OC(C)(C oxopyrrolidin-3-yl]propan- [Middle East 3.2E+07 3.2E+07 6.22 C24H40N4O7 496.604 SBHUNCJSGGMNPS-LNLFQRSKSA-N2.275 3 0 y Inhibitor IC50 muM 0.6 )C)C(=O)N[C@@H](C[C 2-yl}amino)pentan-2- respiratory @@H]1CCNC1=O)C=O syndrome yl]carbamoyl}oxy)piperidin syndrome coronavir e-1-carboxylate coronavirus] us

Middle ethyl 4-([{(S)-4-methyl-1- Replicase East oxo-1-[{(S)-1-oxo-3-[(S)-2- polyprotein 1ab CCOC(=O)N1CCC(CC1)O respirator C(=O)N[C@@H](CC(C)C) oxopyrrolidin-3-yl]propan- [Middle East 3.2E+07 3.2E+07 6.22 C22H36N4O7 468.55 YYTRYFVBTGDGMR-BQFCYCMXSA-N1.398 3 0 y Inhibitor IC50 muM 0.6 C(=O)N[C@@H](C[C@@ 2-yl}amino]pentan-2- respiratory H]1CCNC1=O)C=O syndrome yl}carbamoyl]oxy)piperidin syndrome coronavir e-1-carboxylate coronavirus] us

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-(butylcarbamoyl)- CCCCNC(=O)C(=O)[C@H 1-oxo-3-[(3S)-2- ](C[C@@H]1CCNC1=O) oxopyrrolidin-3-yl]propan- 3CL protease Coronavir NC(=O)[C@H](CC(C)C)N 3.3E+07 3.3E+07 6.22 C33H46N6O7S 670.83 GKSGNHPHNGKDME-CQJMVLFOSA-N1.908 2 0 Inhibitor pIC50 no unit 6.22 C(=O)[C@H](CC1=NC=C( 2-yl]carbamoyl}-3- [Coronavirinae] inae C)S1)NC(=O)OCC1=CC= CC=C1 methylbutyl]carbamoyl}-2- (5-methyl-1,3-thiazol-2- yl)ethyl]carbamate Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C [Middle East respirator )NC(=O)OC2CCC(CC2)C2 3.3E+07 3.3E+07 6.22 C26H38N3O8S*Na575.659 OOMCVQYVJKFVMJ-NEEZWBNRSA-M1.823 2 0 respiratory y Inhibitor IC50 muM 0.6 =CC=CC=C2)C(O)S([O- syndrome syndrome ])(=O)=O)CCNC1=O coronavirus] coronavir us

[Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C 3C-like protease Coronavir )NC(=O)OCCC2=CC=CC( 3.3E+07 3.3E+07 6.22 C22H31ClN3O8S*Na556.012 ZIVZAVLWWUPQGT-FCSMXUNPSA-M1.105 2 0 Inhibitor EC50 muM 0.6 Cl)=C2)C(O)S([O- [Coronavirinae] inae ])(=O)=O)CCNC1=O

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @H](CC1=CC=CC2=C1C SARS =CC=C2)NC(=O)OCC1=C product of 2.4E+07 2.4E+07 6.21 C38H47N5O7 685.82 GCYUVLWAEVVUEN-MCEBTLFFSA-N4.651 2 0 coronavir IC50 muM 0.61 C=CC=C1)C(=O)N[C@@ Replicase H](C[C@@H]1CCNC1=O us )C(=O)C(=O)NC(C)C polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=CC(C)=CC=C1) 1-[(propan-2- NC(=O)OCC1=CC=CC=C 3CL protease Coronavir 3.3E+07 3.3E+07 6.21 yl)carbamoyl]propan-2- C35H47N5O7 649.787 PVFWUORFJWPPGL-DZUOILHNSA-N3.822 2 0 Inhibitor pIC50 no unit 6.21 1)C(=O)N[C@@H](C[C@ [Coronavirinae] inae @H]1CCNC1=O)C(=O)C( yl]carbamoyl}butyl]carbam =O)NC(C)C oyl}-2-(3- methylphenyl)ethyl]carba mate

benzyl N-[(2S)-1-[(2S)-4,4- diethyl-2-{[(2S)-1-oxo-3- CCC1(CC)C[C@H](N(C1) [(3S)-2-oxopyrrolidin-3-yl]- C(=O)[C@H](CC1=CC=C( 1-[(propan-2- 3CL protease Coronavir F)C=C1)NC(=O)OCC1=C 3.3E+07 3.3E+07 6.21 C37H48FN5O7693.816 AFQMPDIGRFCOHN-SYKYGTKKSA-N4.166 2 0 Inhibitor pIC50 no unit 6.21 C=CC=C1)C(=O)N[C@@ yl)carbamoyl]propan-2- [Coronavirinae] inae H](C[C@@H]1CCNC1=O )C(=O)C(=O)NC(C)C yl]carbamoyl}pyrrolidin-1- yl]-3-(4-fluorophenyl)-1- oxopropan-2-yl]carbamate

ClC1=CC=CC(COC(=O)N[ 3C-like protease Coronavir C@@H](CC2CCCCC2)C( 3.2E+07 3.2E+07 6.2 C24H32ClN3O5477.988 FXHORQMDGKYJLY-JBACZVJFSA-N4.318 4 1 Inhibitor IC50 muM 0.63 =O)N[C@@H](C[C@@H [Coronavirinae] inae ]2CCNC2=O)C=O)=C1

(R)-N-(3- CNC(=O)C1=CC=CC(CNC (methylcarbamoyl)benzyl)- Papain-like SARS (=O)C2CCN(CC2)[C@H]( 2.7E+07 2.7E+07 6.2 1581755-37-4 C27H31N3O2 429.562 SCVNWDHTXJYWQM-LJQANCHMSA-N4.386 4 2 IC50 muM 0.63 C)C2=CC=CC3=CC=CC=C 1-(1-(naphthalen-1-yl)- protease [SARS coronavir 23)=C1 ethyl)piperidine-4- coronavirus] us carboxamide

CCCC[C@H](NC(=O)[C@ H](CCC(O)=O)NC(=O)[C @H](CC1=CC=C(O)C=C1 )NC(=O)[C@@H](NC(=O )[C@H](CC(C)C)NC(=O)[ Middle C@H](CC(O)=O)NC(=O)[ spike protein East C@H](CC(C)C)NC(C)=O)[ C@@H](C)O)C(=O)N[C [Middle East respirator @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 6.2 C119H191N25O352531.97 FTNDXEAVLOXOEU-WPJBOECXSA-N1.123 1 0 respiratory y Inhibitor EC50 muM 0.63 @@H](CO)C(=O)N[C@ syndrome syndrome @H](CC(C)C)C(=O)N[C@ @H](CCC(N)=O)C(=O)N[ coronavirus] coronavir C@@]1(C)CCCC=CCCC[C us @](C)(NC(=O)[C@H](CC CCN)NC(=O)[C@@H](N C(=O)[C@@H](NC1=O)C (C)C)C(C)C)C(=O)N[C@

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage @@H](NC(=O)COC1=CC SARS =C(C=C1)N(C)C)C(C)C)C( product of 2.3E+07 2.3E+07 6.19 1383923-00-9 C35H46N6O6S678.853 VEMALIBHQMNWOA-GCIMQLSOSA-N3.516 2 0 coronavir IC50 muM 0.65 =O)N[C@@H](C[C@@H Replicase ]1CCNC1=O)C(=O)C1=N us C2=CC=CC=C2S1 polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CCOC(=O)\C=C\[C@H](C (cleavage [C@@H]1CCNC1=O)NC( Coronavir =O)[C@H](CC(C)C)NC(= 1.1E+07 1.1E+07 6.18 C30H44N4O7 572.702 WDMSWWUPIMEGNZ-SGFFKCJDSA-N3.617 2 0 product of Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards Coronavirus0.66 (SARS CoV) GST-3C-like protease (75 nM) expressed in Escherichia coli using 15 uM SITSAVLQSGFRKMA substrate in 20 mM Tris-HCl (pH 7.5) at 25 degree C for 30 min idae O)[C@@H](NC(=O)OCC Replicase 1=CC=CC=C1)C(C)C polyprotein 1ab) [Coronaviridae] 3C-like proteinase CCOC(=O)\C=C\[C@H](C (cleavage SARS [C@@H]1CCNC1=O)NC( product of =O)[C@H](CC(C)C)NC(= 2.4E+07 2.4E+07 6.18 C30H44N4O7 572.702 coronavir Ki (inhibitionmuM constant) 0.66 Replicase O)[C@@H](NC(=O)OCC us 1=CC=CC=C1)C(C)C polyprotein 1ab) [SARS coronavirus]

1-[(R)-1-(1-naphthyl)ethyl]- C[C@@H](N1CCC(CC1)C 4-[3,4- Papain-like SARS (=O)NCC1=CC2=C(OCO2 2.1E+07 2.1E+07 6.17 1234195-91-5 C26H28N2O3 416.52 IVXBCFLWMPMSAP-GOSISDBHSA-N4.47 4 2 IC50 muM 0.67 )C=C1)C1=C2C=CC=CC2 (methylenedioxy)benzylam protease [SARS coronavir =CC=C1 ino]carbonylpiperidine; coronavirus] us GRL-0667S

SARS COC1=CC(=CC=C1O)C12 helicase [SARS OC3(O)CC(O)(CC(O)(C3) 2.5E+07 2.5E+07 6.17 C14H16O8 312.276 HEBOXBAVJPCGPL-UHFFFAOYSA-N-0.524 4 2 coronavir Inhibitor Inhibition ofIC50 ATPase activitymuM of SARS= coronavirus helicase0.68 coronavirus] O1)O2 us

2-((4- Main proteinase SARS ClC1=CC=C(SSC2=NC=C 3.1E+07 3.1E+07 6.16 C10H7ClN2S2 254.764 SPHGDOQAQWNVCF-UHFFFAOYSA-N2.89 4 2 Inhibitor IC50 muM 0.684 C=N2)C=C1 chlorophenyl)disulfanyl)py (Mpro) [SARS coronavir rimidine coronavirus] us

2-((4- Main proteinase SARS BrC1=CC=C(SSC2=NC=C 3.1E+07 3.1E+07 6.16 C10H7BrN2S2 299.215 OAGXVFKPJKFNDS-UHFFFAOYSA-N3.066 4 2 Inhibitor IC50 muM 0.697 C=N2)C=C1 bromophenyl)disulfanyl)py (Mpro) [SARS coronavir rimidine coronavirus] us

O=C[C@H](C[C@@H]1C 3C-like protease Coronavir CNC1=O)NC(=O)[C@H]( 3.2E+07 3.2E+07 6.16 C24H33N3O5 443.543 YDHLZYPCVKECFG-ACRUOGEOSA-N3.696 4 1 Inhibitor IC50 muM 0.69 CC1CCCCC1)NC(=O)OCC [Coronavirinae] inae 1=CC=CC=C1

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CN product of 1.6E+07 1.6E+07 6.16 1007552-03-5 C11H7ClN2O2234.642 ARSVVAZBFAERQJ-UHFFFAOYSA-N1.642 4 2 coronavir IC50 nM 697 =CC=C2)=CN=C1 Replicase us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS ClC1=CC(OC(=O)C2=CC( product of =CC=C2)N(=O)=O)=CN= 1.6E+07 1.6E+07 6.16 1007552-06-8 C12H7ClN2O4278.652 GDFHBGYIOKPUFO-UHFFFAOYSA-N2.786 4 2 coronavir IC50 nM 684 Replicase C1 us polyprotein 1ab) [SARS coronavirus]

phenylmercuric acetate; phenylmercury(II) acetate; Severe Acute phenyl mercuric acetate; Respiratory SARS CC(=O)O[Hg]C1=CC=CC= 3662930 3662930 6.15 62-38-4 C8H8HgO2 336.74 XEBWQGVWTUSTLN-UHFFFAOYSA-M2.254 4 2 Inhibitor Inhibition constantKi (inhibition againstmuM constant) Severe acute= respiratory syndrome-Corona0.7 virus 3C-like protein (SARS-CoV 3CLpro) was measured; Competitive inhibition C1 phenyl-mercuric acetate; Syndrome-Cov coronavir phenylmercury acetate; 3Clpro [SARS us phenylmercuriacetate; coronavirus] PMA

3C-like phenylmercuric acetate; proteinase phenylmercury(II) acetate; (cleavage phenyl mercuric acetate; SARS CC(=O)O[Hg]C1=CC=CC= product of 3662930 3662930 6.15 62-38-4 phenyl-mercuric acetate; C8H8HgO2 336.74 XEBWQGVWTUSTLN-UHFFFAOYSA-M2.254 4 2 coronavir Radioligand (/ligand)In vitro bindingKi (inhibition affinity ofmuM constant) the compound= towards 3C-like0.7 protease from SARS-CoV C1 Replicase phenylmercury acetate; us polyprotein 1ab) phenylmercuriacetate; [SARS PMA coronavirus]

Tanshinone I; 1,6-dimethyl- phenanthreno[1,2-b]furan- 10,11-diketone; 1,6- dimethylnaphtho[1,2- Papain-like SARS CC1=COC2=C1C(=O)C(= g][1]benzofuran-10,11- O)C1=C3C=CC=C(C)C3= 237369 237369 6.15 568-73-0 C18H12O3 276.291 AIGAZQPHXLWMOJ-UHFFFAOYSA-N3.769 4 2 protease [SARS coronavir IC50 muM 0.7 dione; 1,6- CC=C21 coronavirus] us dimethylphenanthro[1,2- b]furan-10,11-dione; tanshinone IIA; tanshinone I; tanshinone-1 sodium (2S)-2-((S)-2- (((benzyloxy)carbonyl)ami [Na+].CC(C)C[C@H](NC( no)-4-methylpentanamido)- 3C-like protease Coronavir =O)OCC1=CC=CC=C1)C( 2.3E+07 2.3E+07 6.15 1416992-39-6 C21H30N3O8S*Na507.54 BSPJDKCMFIPBAW-JPBGFCRCSA-M0.325 2 0 Inhibitor IC50 muM 0.7 =O)N[C@@H](CC1CCNC 1-hydroxy-3-(2- [Coronavirinae] inae 1=O)C(O)S([O-])(=O)=O oxopyrrolidin-3-yl)propane- 1-sulfonate

3CLpro (3- COC1=NC=CC=C1C1=CC chymotrypsin- SARS =C(C=C1)N(CC1=CSC=C1 2.4E+07 2.4E+07 6.15 C25H21N5O2S 455.54 NGIZLVDUIAGJQR-UHFFFAOYSA-N4.317 4 2 IC50 muM 0.7 )C(=O)CN1N=NC2=C1C= like protease) coronavir CC=C2 [SARS us coronavirus]

sodium (2S)-2-{(S)-2-[({[4- Middle benzyl-1-(tert- Replicase East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- polyprotein 1ab =O)OC1(CC2=CC=CC=C2 respirator )CCN(CC1)C(=O)OC(C)(C 4-yl]oxy}carbonyl)amino]-4- [Middle East 3.2E+07 3.2E+07 6.15 C31H47N4O10S*Na690.791 GODLXHBNULFSDU-WYYMQYPJSA-M2.133 2 0 y Inhibitor IC50 muM 0.7 )C)C(=O)N[C@@H](C[C methylpentanamido}-1- respiratory @@H]1CCNC1=O)C(O)S syndrome hydroxy-3-[(S)-2- syndrome ([O-])(=O)=O coronavir oxopyrrolidin-3-yl]propane- coronavirus] us 1-sulfonate

4-benzyl-1- Middle Replicase (methylsulfonyl)piperidin- East CC(C)C[C@H](NC(=O)OC polyprotein 1ab 4-yl {(S)-4-methyl-1-oxo-1- respirator 1(CC2=CC=CC=C2)CCN( [Middle East CC1)S(C)(=O)=O)C(=O)N 3.2E+07 3.2E+07 6.15 [{(S)-1-oxo-3-[(S)-2- C27H40N4O7S564.703 ZLOZUJAXLMKVNG-VABKMULXSA-N2.471 2 0 y Inhibitor IC50 muM 0.7 respiratory [C@@H](C[C@@H]1CC oxopyrrolidin-3-yl]propan- syndrome NC1=O)C=O syndrome 2-yl}amino]pentan-2- coronavir coronavirus] yl}carbamate us

1- Middle Replicase (methylsulfonyl)piperidin- East polyprotein 1ab CC(C)C[C@H](NC(=O)OC 4-yl {(S)-4-methyl-1-oxo-1- respirator 1CCN(CC1)S(C)(=O)=O)C [Middle East 3.2E+07 3.2E+07 6.15 [{(S)-1-oxo-3-[(S)-2- C20H34N4O7S474.579 POHZAMMIKLXFHR-ZOBUZTSGSA-N0.609 3 0 y Inhibitor IC50 muM 0.7 (=O)N[C@@H](C[C@@ respiratory H]1CCNC1=O)C=O oxopyrrolidin-3-yl]propan- syndrome syndrome 2-yl}amino]pentan-2- coronavir coronavirus] yl}carbamate us

Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C [Middle East respirator )NC(=O)OCCC2=CC=CC( 3.3E+07 3.3E+07 6.15 C22H31ClN3O8S*Na556.012 ZIVZAVLWWUPQGT-FCSMXUNPSA-M1.105 2 0 respiratory y Inhibitor IC50 muM 0.7 Cl)=C2)C(O)S([O- syndrome syndrome ])(=O)=O)CCNC1=O coronavirus] coronavir us

Middle 3C-like protease East [Na+].[H][C@@]1(C[C@ H](NC(=O)[C@H](CC(C)C [Middle East respirator )NC(=O)OCCCCCCCCCC) 3.3E+07 3.3E+07 6.15 C24H44N3O8S*Na557.684 HHNLARZINPTEJR-SJZJPLIYSA-M3.379 2 0 respiratory y Inhibitor EC50 muM 0.7 C(O)S([O- syndrome syndrome ])(=O)=O)CCNC1=O coronavirus] coronavir us

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage SARS @@H](NC(=O)[C@H](C) product of NC(=O)OCC1=CC=CC=C 1.9E+07 1.9E+07 6.14 1034140-83-4 C32H41F3N4O6634.696 PDLFIYNGGUUVLF-GLMUFQRRSA-N5.092 2 0 coronavir Radioligand (/ligand)Binding affinityKi (inhibition of the compoundmuM constant) towards= SARS-CoV 3C-like0.73 protease in 20 mM Bis-Tris buffer, pH 7.0 at 25 degree C for 2 h Replicase 1)C(C)C)C(=O)NC(CC1=C us C=CC=C1)C(=O)C(F)(F)F polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS Benzyloxycarbonyl- product of No Structure 2.5E+07 2.5E+07 6.14 coronavir Ki (inhibitionmuM constant) 0.73 AVLF(D/L)-Trifluoromethyl Replicase us polyprotein 1ab) [SARS coronavirus]

benzyl N-[(1S)-1-{[(1S)-1- {[(2S)-1-{[(1S)-1- CC(C)C[C@H](NC(=O)[C cyclohexylethyl]carbamoyl @H](CC1=NC=CC=C1)N }-1-oxo-3-[(3S)-2- C(=O)OCC1=CC=CC=C1) 3CL protease Coronavir C(=O)N[C@@H](C[C@@ 3.3E+07 3.3E+07 6.13 oxopyrrolidin-3-yl]propan- C38H52N6O7 704.867 KIPIKDUHBLLVGS-OOZDRQTLSA-N4.244 2 0 Inhibitor pIC50 no unit 6.13 [Coronavirinae] inae H]1CCNC1=O)C(=O)C(= 2-yl]carbamoyl}-3- O)N[C@@H](C)C1CCCC C1 methylbutyl]carbamoyl}-2- (pyridin-2- yl)ethyl]carbamate

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CN1CCCCC1)NC(= 1-[(propan-2- 3CL protease Coronavir O)OCC1=CC=CC=C1)C(= 3.3E+07 3.3E+07 6.13 C33H50N6O7 642.796 YAPXNEGFZWHFBS-FWEHEUNISA-N2.234 2 0 Inhibitor pIC50 no unit 6.13 O)N[C@@H](C[C@@H] yl)carbamoyl]propan-2- [Coronavirinae] inae 1CCNC1=O)C(=O)C(=O) NC(C)C yl]carbamoyl}butyl]carbam oyl}-2-(piperidin-1- yl)ethyl]carbamate 3C-like proteinase COC1=CC=CC(OCC(=O)N (cleavage [C@@H](C(C)C)C(=O)N[ SARS C@@H](CC(C)C)C(=O)N[ product of 2.3E+07 2.3E+07 6.12 1383922-88-0 C34H43N5O7S665.811 IWZSFDORUMHIJN-KXDOSHFCSA-N3.222 3 0 coronavir IC50 muM 0.75 C@@H](C[C@@H]2CCN Replicase C2=O)C(=O)C2=NC3=CC us =CC=C3S2)=C1 polyprotein 1ab) [SARS coronavirus]

(+/-)-cryptotanshinone; (+/- )-chryptotanshinone; cryptotanshinone; crytotanshinone; 1,6,6- trimethyl-1,2,6,7,8,9- SARS CC1COC2=C1C(=O)C(=O hexahydro-phenanthro[1,2- Plpro [SARS )C1=C3CCCC(C)(C)C3=C 288778 288778 6.1 17545-07-2; 35825-57-1 C19H20O3 296.366 GVKKJJOMQCNPGB-UHFFFAOYSA-N4.152 4 2 coronavir Inhibitory concentrationIC50 muM of the compound= against Severe0.8 acute respiratory syndrome Coronavirus (SARS CoV) Plpro (PL Protease, 54 nM) expressed in Escherichia coli BL21-CodonPlus(DE3)-RIL cells using 30 uM RLRGG-AMC (Arg-Leu-Arg-Gly-Gly-AMC) as a fluorogenic peptide substrate upon preincubation in 20 mM Tris-HCl, pH 6.8 at 37 degree C for 30 minutes b]furan-10,11-dione; 1,6,6- coronavirus] C=C21 us trimethyl-1,2,6,7,8,9- hexahydro-phenanthro[1,2- b]furan-10,11-quinone; 1,6,6-Trimethyl-1,2,6,7,8,9- hexahydro-phenanthro[1,2- (S)-3- benzyloxycarbonylamino-5- bromo-4-oxo-pentanoic 3C-like acid tert-butyl ester; (3S)-3- proteinase (N- (cleavage SARS CC(C)(C)OC(=O)C[C@H]( benzyloxycarbonyl)amino- product of NC(=O)OCC1=CC=CC=C 6820432 6820432 6.1 153088-76-7 C17H22BrNO5400.269 PBVFTOAYKLEQQO-ZDUSSCGKSA-N3.077 4 1 coronavir Radioligand (/ligand) Kd (dissociationnM constant) 800 5-bromo-4-oxopentanoic Replicase 1)C(=O)CBr us acid tert-butyl ester; (S)-3- polyprotein 1ab) benzyloxycarbonylamino-5- [SARS bromo-4-oxopentanoic coronavirus] acid tert-butyl ester; (S)- tert-butyl 3-

3C-like proteinase [H][C@@]12CC(C)=CC[C (cleavage SARS @]1(C)CC[C@]1(C)C3=C Iguesterin; iguesterin; product of C=C4C(C)=C(O)C(=O)C= 2184039 2184039 6.1 53527-47-2 C28H36O2 404.593 FLMDVQMCMIGPEK-IPTPSVHJSA-N8.906 3 2 coronavir Ki (inhibitionmuM constant) 0.8 iguestrin; Iguestresin Replicase C4[C@]3(C)CC[C@@]21 us C polyprotein 1ab) [SARS coronavirus]

3C-like proteinase CC(C)C[C@H](NC(=O)[C (cleavage SARS @@H](NC(=O)[C@H](C) product of NC(=O)OCC1=CC=CC=C 1.9E+07 1.9E+07 6.1 1034140-83-4 C32H41F3N4O6634.696 PDLFIYNGGUUVLF-GLMUFQRRSA-N5.092 2 0 coronavir Inhibitor Inhibitory concentrationIC50 muM of the compoud= against SARS-CoV0.8 3C-like protease in 20 mM Bis-Tris buffer, pH 7.0 at 25 degree C for 4 h Replicase 1)C(C)C)C(=O)NC(CC1=C us C=CC=C1)C(=O)C(F)(F)F polyprotein 1ab) [SARS coronavirus]

tert-butyl 4-benzyl-4-([{(S)- Middle Replicase 4-methyl-1-oxo-1-[{(S)-1- East CC(C)C[C@H](NC(=O)OC polyprotein 1ab oxo-3-[(S)-2-oxopyrrolidin- respirator 1(CC2=CC=CC=C2)CCN( [Middle East CC1)C(=O)OC(C)(C)C)C(= 3.2E+07 3.2E+07 6.1 3-yl]propan-2- C31H46N4O7 586.729 UGEDYCZHWKTZHO-SDHOMARFSA-N4.137 2 0 y Inhibitor IC50 muM 0.8 respiratory O)N[C@@H](C[C@@H] yl}amino]pentan-2- syndrome 1CCNC1=O)C=O syndrome yl}carbamoyl]oxy)piperidin coronavir coronavirus] e-1-carboxylate us

sodium (2S)-2-{(S)-2-[({[4- Middle benzyl-1-(tert- Replicase East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- polyprotein 1ab =O)OC1(CC2=CC=CC=C2 respirator )CCN(CC1)C(=O)OC(C)(C 4-yl]oxy}carbonyl)amino]-4- [Middle East 3.2E+07 3.2E+07 6.1 C31H47N4O10S*Na690.791 GODLXHBNULFSDU-WYYMQYPJSA-M2.133 2 0 y Inhibitor EC50 muM 0.8 )C)C(=O)N[C@@H](C[C methylpentanamido}-1- respiratory @@H]1CCNC1=O)C(O)S syndrome hydroxy-3-[(S)-2- syndrome ([O-])(=O)=O coronavir oxopyrrolidin-3-yl]propane- coronavirus] us 1-sulfonate

sodium (2S)-2-{(S)-2-[({[4- Middle benzyl-1-(tert- 3C-like protease East [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- =O)OC1(CC2=CC=CC=C2 [Middle East respirator )CCN(CC1)C(=O)OC(C)(C 4-yl]oxy}carbonyl)amino]-4- 3.2E+07 3.2E+07 6.1 C31H47N4O10S*Na690.791 GODLXHBNULFSDU-WYYMQYPJSA-M2.133 2 0 respiratory y Inhibitor EC50 muM 0.8 )C)C(=O)N[C@@H](C[C methylpentanamido}-1- @@H]1CCNC1=O)C(O)S syndrome syndrome hydroxy-3-[(S)-2- ([O-])(=O)=O coronavirus] coronavir oxopyrrolidin-3-yl]propane- us 1-sulfonate

sodium (2S)-2-{(S)-2-[({[4- benzyl-1-(tert- [Na+].CC(C)C[C@H](NC( butoxycarbonyl)piperidin- =O)OC1(CC2=CC=CC=C2 4-yl]oxy}carbonyl)amino]-4- 3C-like protease Coronavir )CCN(CC1)C(=O)OC(C)(C 3.2E+07 3.2E+07 6.1 C31H47N4O10S*Na690.791 GODLXHBNULFSDU-WYYMQYPJSA-M2.133 2 0 Inhibitor EC50 muM 0.8 )C)C(=O)N[C@@H](C[C methylpentanamido}-1- [Coronavirinae] inae @@H]1CCNC1=O)C(O)S ([O-])(=O)=O hydroxy-3-[(S)-2- oxopyrrolidin-3-yl]propane- 1-sulfonate

3C-like proteinase (cleavage SARS Benzyloxycarbonyl- product of No Structure 2.5E+07 2.5E+07 6.1 coronavir IC50 muM 0.8 AVLF(D/L)-Trifluoromethyl Replicase us polyprotein 1ab) [SARS coronavirus]

Severe Acute CC1=CC[C@]2(C)CC[C@] Respiratory 3(C)C4=CC=C5C(C)=C(O) Coronavir 2.6E+07 2.6E+07 6.1 C28H36O2 404.593 FLMDVQMCMIGPEK-VAPXRUTMSA-N8.906 3 2 Syndrome-Cov Inhibitor Inhibition constantKi (inhibition of themuM constant) compound= towards corona virus0.8 3CL protease using 10 uM Dabcyl-KNSTLQSGLRKE-Edans as peptide substrate upon incubation in 20 mM Bis-Tris buffer for 60 min at 25 degree C C(=O)C=C5[C@]4(C)CC[ idae C@@]3(C)C2C1 3Clpro [Coronaviridae] N-(4-(2-(1H- CC(C)C(=O)NC1=CC=C(C benzo[d][1,2,3]triazol-1-yl)- 3C-like protease SARS =C1)N(C(C(=O)NCC1=CC N-(2-(benzylamino)-1-(4- =CC=C1)C1=CC=C(Cl)C(F 3.2E+07 3.2E+07 6.1 C33H30ClFN6O3613.091 ISHXMYLDUPUTFN-UHFFFAOYSA-N4.924 3 1 [SARS coronavir Inhibitor IC50 muM 0.8 chloro-3-fluorophenyl)-2- )=C1)C(=O)CN1N=NC2= coronavirus] us CC=CC=C12 oxoethyl)acetamido)pheny l)isobutyramide

benzyl N-[(1S)-2-(4- fluorophenyl)-1-{[(1S)-3- CC(C)C[C@H](NC(=O)[C methyl-1-{[(2S)-1-oxo-3- @H](CC1=CC=C(F)C=C1) [(3S)-2-oxopyrrolidin-3-yl]- 3CL protease Coronavir NC(=O)OCC1=CC=CC=C 3.3E+07 3.3E+07 6.09 C34H44FN5O7653.751 ZUZMPCWEWWIPQX-VNNZRSTGSA-N3.546 2 0 Inhibitor pIC50 no unit 6.09 1)C(=O)N[C@@H](C[C@ 1-[(propan-2- [Coronavirinae] inae @H]1CCNC1=O)C(=O)C( =O)NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

[H][C@@]1(C[C@H](NC( =O)[C@H](CC(C)C)NC(= 3C-like protease Coronavir O)OCC2=CC=CC=C2)C(= 3.4E+07 3.4E+07 6.08 C28H40N4O6 528.649 XOIKFGSURVWBBG-PMVMPFDFSA-N3.187 3 0 Inhibitor IC50 muM 0.83 O)C(=O)NC2CCCCC2)CC [Coronavirinae] inae NC1=O

[Na+].OC([C@H](C[C@ @H]1CCNC1=O)NC(=O)[ 3C-like protease Coronavir C@H](CC1CCCCC1)NC(= 3.2E+07 3.2E+07 6.07 C24H34N3O8S*Na547.605 QIIXTKHVLHZPQZ-SJZJPLIYSA-M1.692 2 0 Inhibitor IC50 muM 0.86 O)OCC1=CC=CC=C1)S([ [Coronavirinae] inae O-])(=O)=O

[H][C@@]1(C[C@H](NC( 3C-like protease Coronavir =O)[C@H](CC(C)C)NC(= 3.4E+07 3.4E+07 6.06 C21H28ClN3O5437.923 ORVJRZJFKNTOQG-SZMVWBNQSA-N2.951 4 1 Inhibitor IC50 muM 0.88 O)OCC2=CC=CC(Cl)=C2) [Coronavirinae] inae C=O)CCNC1=O

Middle sodium (2S)-2-((S)-2- 3C-like protease East (((benzyloxy)carbonyl)ami [Na+].CC(C)C[C@H](NC( [Middle East respirator =O)OCC1=CC=CC=C1)C( no)-4-methylpentanamido)- 2.3E+07 2.3E+07 6.05 1416992-39-6 C21H30N3O8S*Na507.54 BSPJDKCMFIPBAW-JPBGFCRCSA-M0.325 2 0 respiratory y Inhibitor EC50 muM 0.9 =O)N[C@@H](CC1CCNC 1-hydroxy-3-(2- 1=O)C(O)S([O-])(=O)=O syndrome syndrome oxopyrrolidin-3-yl)propane- coronavirus] coronavir 1-sulfonate us

2-((2- nitrophenyl)disulfanyl)pyri midine; 2-(2-nitro- Main proteinase SARS O=N(=O)C1=C(SSC2=NC 804680 804680 6.05 C10H7N3O2S2265.316 ADRGABKQRZRTKB-UHFFFAOYSA-N2.16 4 2 Inhibitor IC50 muM 0.883 =CC=N2)C=CC=C1 phenyldisulfanyl)- (Mpro) [SARS coronavir pyrimidine; 2-(2'- coronavirus] us Nitrophenyldithio)- pyrimidin

3C-like proteinase (cleavage Cl\C(Cl)=C(\Cl)C(=O)OC1 SARS =CC=C(C=C1)S(=O)(=O)C product of 1.1E+07 1.1E+07 6.05 C18H8Cl6O6S 565.042 HXYPMMAPDRFFTM-UHFFFAOYSA-N6.49 2 2 coronavir IC50 muM 0.9 1=CC=C(OC(=O)C(\Cl)=C Replicase (/Cl)Cl)C=C1 us polyprotein 1ab) [SARS coronavirus]

sodium (2S)-2-{(S)-2-[({[4- Middle benzyl-1- Replicase East [Na+].CC(C)C[C@H](NC( (methylsulfonyl)piperidin- polyprotein 1ab =O)OC1(CC2=CC=CC=C2 respirator )CCN(CC1)S(C)(=O)=O)C( 4-yl]oxy}carbonyl)amino]-4- [Middle East 3.2E+07 3.2E+07 6.05 C27H41N4O10S2*Na668.765 PVFOFJYHUDKJAA-FLABFKKQSA-M0.467 2 0 y Inhibitor IC50 muM 0.9 =O)N[C@@H](C[C@@H methylpentanamido}-1- respiratory ]1CCNC1=O)C(O)S([O- syndrome hydroxy-3-[(S)-2- syndrome ])(=O)=O coronavir oxopyrrolidin-3-yl]propane- coronavirus] us 1-sulfonate

CSCC[C@H](NC(=O)[C@ H](CCC(O)=O)NC(=O)[C @H](CC1=CC=C(O)C=C1 )NC(=O)[C@@H](NC(=O )[C@H](CC(C)C)NC(=O)[ Middle C@H](CC(O)=O)NC(=O)[ spike protein East C@H](CC(C)C)NC(C)=O)[ C@@H](C)O)C(=O)N[C [Middle East respirator @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 6.05 C120H192N26O35S2591.06 ZEXNMYVOVAJSAS-PKYRURSASA-N0.906 1 0 respiratory y Inhibitor EC50 muM 0.89 @@H](CO)C(=O)N[C@ syndrome syndrome @H](CC(C)C)C(=O)N[C@ @H](CCC(N)=O)C(=O)N[ coronavirus] coronavir C@@H](CCC(N)=O)C(=O us )N[C@@H](C(C)C)C(=O) N[C@@H](C(C)C)C(=O) N[C@@H](CCCCN)C(=O) N[C@@]1(C)CCCC=CCC 4,6-dimethyl-2-((2- Main proteinase SARS CC1=CC(C)=NC(SSC2=CC 3.1E+07 3.1E+07 6.04 C12H11N3O2S2293.37 OXOOBQWVUHEGBI-UHFFFAOYSA-N2.79 4 2 Inhibitor IC50 muM 0.921 =CC=C2N(=O)=O)=N1 nitrophenyl)disulfanyl)pyri (Mpro) [SARS coronavir midine coronavirus] us

3C-like proteinase COC1=CC=C(OCC(=O)N[ (cleavage C@@H](C(C)C)C(=O)N[C SARS @@H](CC(C)C)C(=O)N[C product of 2.3E+07 2.3E+07 6.04 1383922-80-2 C34H43N5O7S665.811 DYFSDLMESFFYEO-KXDOSHFCSA-N3.222 3 0 coronavir IC50 muM 0.92 @@H](C[C@@H]2CCNC Replicase 2=O)C(=O)C2=NC3=CC= us CC=C3S2)C=C1 polyprotein 1ab) [SARS coronavirus]

benzyl ((S)-1-(((S)-1-(((S)-4- (isopropylamino)-3,4-dioxo- 1-((S)-2-oxopyrrolidin-3- yl)butan-2-yl)amino)-4- CC(C)C[C@H](NC(=O)[C @H](CC1=NC(=CC=C1)C methyl-1-oxopentan-2- (F)(F)F)NC(=O)OCC1=CC yl)amino)-1-oxo-3-(6- 3CL protease Coronavir 3.3E+07 3.3E+07 6.04 C34H43F3N6O7704.747 DQTFXZMNCOWPBY-GKXKVECMSA-N3.236 2 0 Inhibitor pIC50 no unit 6.04 =CC=C1)C(=O)N[C@@H] (trifluoromethyl)pyridin-2- [Coronavirinae] inae (C[C@@H]1CCNC1=O)C (=O)C(=O)NC(C)C yl)propan-2-yl)carbamate; benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- [(3S)-2-oxopyrrolidin-3-yl]- 1-[(propan-2-

Severe Acute

CN(CC(=O)NC1CCCC1)S( Respiratory SARS =O)(=O)C1=CC(Cl)=CC=C 2.7E+07 2.7E+07 6.03 853595-74-1 C14H19ClN2O3S330.835 Syndrome-Cov coronavir Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS0.94 CORONAVIRUS 3CL PROTEASE upon incubation in 50 mM HEPES, pH 7.5 for 1 hr at RT was determined 1 3Clpro [SARS us coronavirus]

benzyl N-[(1S)-1-{[(1S)-3- methyl-1-{[(2S)-1-oxo-3- CC(C)C[C@H](NC(=O)[C [(3S)-2-oxopyrrolidin-3-yl]- @H](CC1=NC=C(C=C1)C 1-[(propan-2- (F)(F)F)NC(=O)OCC1=CC 3CL protease Coronavir 3.3E+07 3.3E+07 6.03 yl)carbamoyl]propan-2- C34H43F3N6O7704.747 PVEAZVRGSPKZRQ-OXCFDMGDSA-N3.147 2 0 Inhibitor pIC50 no unit 6.03 =CC=C1)C(=O)N[C@@H] [Coronavirinae] inae (C[C@@H]1CCNC1=O)C yl]carbamoyl}butyl]carbam (=O)C(=O)NC(C)C oyl}-2-[5- (trifluoromethyl)pyridin-2- yl]ethyl]carbamate

benzyl N-[(1S)-2-(4- fluoropiperidin-1-yl)-1- CC(C)C[C@H](NC(=O)[C {[(1S)-3-methyl-1-{[(2S)-1- @H](CN1CCC(F)CC1)NC( oxo-3-[(3S)-2-oxopyrrolidin- 3CL protease Coronavir =O)OCC1=CC=CC=C1)C( 3.3E+07 3.3E+07 6.03 C33H49FN6O7660.786 HLWOHQINQVCEIR-MNUOIFNESA-N2.378 2 0 Inhibitor pIC50 no unit 6.03 =O)N[C@@H](C[C@@H 3-yl]-1-[(propan-2- [Coronavirinae] inae ]1CCNC1=O)C(=O)C(=O) NC(C)C yl)carbamoyl]propan-2- yl]carbamoyl}butyl]carbam oyl}ethyl]carbamate

benzyl N-[(1S)-3-methyl-1- {[(1S)-3-methyl-1-{[(2S)-1- CC(C)C[C@H](NC(=O)OC oxo-3-[(3S)-2-oxopyrrolidin- C1=CC=CC=C1)C(=O)N[C 3CL protease Coronavir @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 6.03 3-yl]-1-[(propan-2- C31H47N5O7 601.743 HEVXFSPURLYARR-QORCZRPOSA-N3.375 2 0 Inhibitor pIC50 no unit 6.03 [Coronavirinae] inae @@H](C[C@@H]1CCNC yl)carbamoyl]propan-2- 1=O)C(=O)C(=O)NC(C)C yl]carbamoyl}butyl]carbam oyl}butyl]carbamate

3C-like proteinase (cleavage SARS IC1=CC=C2N(CC3=CC4= product of CC=CC=C4S3)C(=O)C(=O 7594653 7594653 6.02 861216-06-0 C17H10INO2S 419.242 MAYSJMBSILUGEG-UHFFFAOYSA-N3.905 4 2 coronavir IC50 muM 0.95 Replicase )C2=C1 us polyprotein 1ab) [SARS coronavirus]

3C-like proteinase (cleavage SARS IC1=CC=C2N(CC3=CC4= product of CC=CC=C4S3)C(=O)C(=O 7594653 7594653 6.02 861216-06-0 C17H10INO2S 419.242 MAYSJMBSILUGEG-UHFFFAOYSA-N3.905 4 2 coronavir Inhibitor In vitro inhibitoryIC50 concentrationmuM of the= compound against0.95 3C-like protease from SARS-CoV Replicase )C2=C1 us polyprotein 1ab) [SARS coronavirus]

Severe Acute

IC1=CC=C2N(CC3=CC4= Respiratory SARS CC=CC=C4S3)C(=O)C(=O 7594653 7594653 6.02 861216-06-0 C17H10INO2S 419.242 MAYSJMBSILUGEG-UHFFFAOYSA-N3.905 4 2 Syndrome-Cov coronavir Inhibitor Inhibitory concentrationIC50 muM of the compound= against SARS0.95 CORONAVIRUS 3CL PROTEASE (0.5 uM) expressed in Escherichia coli BL21 (DE3) cells using 16 uM AVLQSGFRKK as substrate upon incubation in 50 mM Tris-HCl, pH 7.3 at 37 degree C by FLUORESCENCE RESONANCE ENERGY TRANSFER (FRET) ASSAY )C2=C1 3Clpro [SARS us coronavirus]

IC1=CC=C2N(CC3=CSC4 Sars Cov 3C-Like SARS =C3C=CC=C4)C(=O)C(=O 2.5E+07 2.5E+07 6.02 C17H10INO2S 419.242 BQVHRIFPQQYIGO-UHFFFAOYSA-N4.235 4 2 Protease [SARS coronavir Inhibitor Inhibitory concentrationIC50 muM against SARS-CoV= 3C-like protease0.95 was determined using 6 uM of fluorogenic substrate (Dabcyl-KTSAVLQSGFRKME-Edans) in 12 mM Tris-HCl buffer, pH 7.5 incubated at RT for 10 min by FRET method )C2=C1 coronavirus] us Severe Acute

IC1=CC=C2N(CC3=CSC4 Respiratory SARS =C3C=CC=C4)C(=O)C(=O 2.5E+07 2.5E+07 6.02 C17H10INO2S 419.242 BQVHRIFPQQYIGO-UHFFFAOYSA-N4.235 4 2 Syndrome-Cov coronavir Inhibitory concentrationIC50 muM of compound (dissolved in DMSO)0.95 against 3CL Protease from Severe Acute Respiratory Syndrome Coronavirus expressed in Escherichia coli BL21(DE3) upon incubation in 50 mM HEPES, pH 7.5 for 30 minutes at RT )C2=C1 3Clpro [SARS us coronavirus]

Severe Acute

IC1=CC=C2C(CC3=CC4= Respiratory SARS C(S3)C=CC=C4)C(=O)C(= 2.6E+07 2.6E+07 6.02 C18H11IO2S 418.255 CWBDSMSNJTZRSA-UHFFFAOYSA-N4.147 4 2 Syndrome-Cov coronavir Inhibitor Inhibitory activityIC50 againstmuM Severe acute= respiratory syndrome-Corona0.95 virus 3C-like protein (SARS-CoV 3CLpro) was determined O)C2=C1 3Clpro [SARS us coronavirus]

ClC1=CC=CC(COC(=O)N[ 3C-like protease Coronavir C@@H](CC2CCCCC2)C( 3.2E+07 3.2E+07 6.01 C24H32ClN3O5477.988 FXHORQMDGKYJLY-JBACZVJFSA-N4.318 4 1 Inhibitor IC50 muM 0.98 =O)N[C@@H](C[C@@H [Coronavirinae] inae ]2CCNC2=O)C=O)=C1

3CLpro (3- O=C(CN1N=NC2=C1C=C chymotrypsin- SARS C=C2)N(CC1=CSC=C1)C1 2.4E+07 2.4E+07 6.01 C24H19N5OS 425.514 LHBIUOYHJIXRST-UHFFFAOYSA-N3.674 4 2 IC50 muM 0.97 =CC=C(C=C1)C1=CC=CN like protease) coronavir =C1 [SARS us coronavirus]

3C-like proteinase (cleavage SARS BrC1=CC=CC2=C1N(CC1 product of =CC3=C(S1)C=CC=C3)C( 1E+07 1E+07 6.01 C17H10BrNO2S372.242 UFOWXDUBQLPEOX-UHFFFAOYSA-N3.635 4 2 coronavir IC50 muM 0.98 Replicase =O)C2=O us polyprotein 1ab) [SARS coronavirus]

Severe Acute

BrC1=C2C(CC3=CC4=C(S Respiratory SARS 3)C=CC=C4)C(=O)C(=O)C 2.6E+07 2.6E+07 6.01 C18H11BrO2S 371.254 XDCJGGHIPOQMLF-UHFFFAOYSA-N3.877 4 2 Syndrome-Cov coronavir Inhibitor Inhibitory activityIC50 againstmuM Severe acute= respiratory syndrome-Corona0.98 virus 3C-like protein (SARS-CoV 3CLpro) was determined 2=CC=C1 3Clpro [SARS us coronavirus]

BrC1=CC=CC2=C1N(CC1 Sars Cov 3C-Like SARS =CSC3=C1C=CC=C3)C(= 2.6E+07 2.6E+07 6.01 1347890-63-4 C17H10BrNO2S372.242 GSJXYXKSXPVDEN-UHFFFAOYSA-N3.965 4 2 Protease [SARS coronavir Inhibitor Inhibitory concentrationIC50 muM against SARS-CoV= 3C-like protease0.98 was determined using 6 uM of fluorogenic substrate (Dabcyl-KTSAVLQSGFRKME-Edans) in 12 mM Tris-HCl buffer, pH 7.5 incubated at RT for 10 min by FRET method O)C2=O coronavirus] us

Tanshinone I; 1,6-dimethyl- phenanthreno[1,2-b]furan- 10,11-diketone; 1,6- dimethylnaphtho[1,2- CC1=COC2=C1C(=O)C(= g][1]benzofuran-10,11- O)C1=C3C=CC=C(C)C3= 237369 237369 568-73-0 C18H12O3 276.291 AIGAZQPHXLWMOJ-UHFFFAOYSA-N3.769 4 2 CC=C21 dione; 1,6- dimethylphenanthro[1,2- b]furan-10,11-dione; tanshinone IIA; tanshinone I; tanshinone-1

[H][C@@]12CC(C)=CC[C @]1(C)CC[C@]1(C)C3=C Iguesterin; iguesterin; C=C4C(C)=C(O)C(=O)C= 2184039 2184039 53527-47-2 C28H36O2 404.593 FLMDVQMCMIGPEK-IPTPSVHJSA-N8.906 3 2 C4[C@]3(C)CC[C@@]21 iguestrin; Iguestresin C

BrC1=CC(OC(=O)C2=CC= 1.1E+07 1.1E+07 936371-58-3 C10H6BrNO3 268.067 HMICIXHTRIFAET-UHFFFAOYSA-N1.77 4 2 CO2)=CN=C1 (1R,2S,3S,4R,5R)-3-(6- amino-9H-purin-9-yl)-4- NC1=NC=NC2=C1N=CN fluoro-5- 2[C@H]1[C@H](O)[C@H 1E+07 1E+07 C11H14FN5O3283.262 LFSGVDMIBZBPPJ-QCFOWSJWSA-N-0.667 4 2 ](O)[C@@H](CO)[C@H] (hydroxymethyl)cyclopent 1F ane-1,2-diol; (-)-6?-beta- fluoro-aristeromycin; 6'- beta-fluoroaristeromycin

(1R,2S,3S,4R,5R)-3-(6- amino-9H-purin-9-yl)-4- NC1=NC=NC2=C1N=CN fluoro-5- 2[C@H]1[C@H](O)[C@H 1E+07 1E+07 C11H14FN5O3283.262 LFSGVDMIBZBPPJ-QCFOWSJWSA-N-0.667 4 2 ](O)[C@@H](CO)[C@H] (hydroxymethyl)cyclopent 1F ane-1,2-diol; (-)-6?-beta- fluoro-aristeromycin; 6'- beta-fluoroaristeromycin

ClC1=CC(OC(=O)C2=CC= 1.1E+07 1.1E+07 353257-73-5 C10H6ClNO3 223.616 DWJOEJDGHVXXEB-UHFFFAOYSA-N1.594 4 2 CO2)=CN=C1

ClC1=CN=CC(OC(=O)C2 1.1E+07 1.1E+07 C14H9ClN2O2272.691 LJTINUKMKJKLBT-UHFFFAOYSA-N3.06 4 2 =CC3=CC=CC=C3N2)=C1

2-((2- nitrophenyl)disulfanyl)pyri midine; 2-(2-nitro- O=N(=O)C1=C(SSC2=NC 804680 804680 C10H7N3O2S2265.316 ADRGABKQRZRTKB-UHFFFAOYSA-N2.16 4 2 =CC=N2)C=CC=C1 phenyldisulfanyl)- pyrimidine; 2-(2'- Nitrophenyldithio)- pyrimidin

CCOC(=O)\C=C\[C@H](C C1=CC=CC=C1)NC(=O)[C @H](CC1=CC=CC=C1)NC 1.1E+07 1.1E+07 C33H37N3O4 539.674 JWPLKCWYGMPRGX-ZIIPDIQWSA-N5.753 2 1 (=O)\C=C\C1=CC=C(C=C 1)N(C)C

CCOC(=O)\C=C\[C@H](C [C@@H]1CCNC1=O)NC( =O)[C@H](CC(C)C)NC(= 1.1E+07 1.1E+07 C30H44N4O7 572.702 WDMSWWUPIMEGNZ-SGFFKCJDSA-N3.617 2 0 O)[C@@H](NC(=O)OCC 1=CC=CC=C1)C(C)C

CCOC(=O)\C=C\[C@H](C [C@@H]1CCNC1=O)NC( =O)[C@H](CC(C)C)NC(= 1.1E+07 1.1E+07 C30H44N4O7 572.702 WDMSWWUPIMEGNZ-SGFFKCJDSA-N3.617 2 0 O)[C@@H](NC(=O)OCC 1=CC=CC=C1)C(C)C C[C@@H](NC(=O)C1=C( 5-methylamino-2-methyl- C)C=CC(CN)=C1)C1=CC= 2E+07 2E+07 1184301-69-6N-[(R)-1-(1- C21H22N2O 318.418 BIKTWHWUIKAJAT-OAHLLOKOSA-N4.488 4 2 CC2=CC=CC=C12 naphthyl)ethyl]benzamide

1-[(R)-1-(1-naphthyl)ethyl]- COC1=CC=C(CNC(=O)C2 4-(4- CCN(CC2)[C@H](C)C2=C 2.1E+07 2.1E+07 1233939-86-0 C26H30N2O2 402.536 NTMTVRCCLOAJST-LJQANCHMSA-N4.896 4 2 C=CC3=C2C=CC=C3)C=C methoxybenzylamino)carb 1 onylpiperidine

1-[(R)-1-(1-naphthyl)ethyl]- COC1=CC(CNC(=O)C2CC 4-(3- N(CC2)[C@H](C)C2=CC= 2.1E+07 2.1E+07 1233939-85-9 C26H30N2O2 402.536 QKYBTDRNPVPOGN-LJQANCHMSA-N4.896 4 2 CC3=C2C=CC=C3)=CC=C methoxybenzylamino)carb 1 onylpiperidine

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)OCC1=CC =CC=C1)C(C)C)C(=O)N[C 2.3E+07 2.3E+07 1359941-93-7 C33H41N5O6S635.784 KSCRVOKQPYZBHZ-IXPOFIJOSA-N3.789 2 0 @@H](C[C@@H]1CCNC 1=O)C(=O)C1=NC2=CC= CC=C2S1

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)COC1=CC (=CC=C1)N(C)C)C(C)C)C( 2.3E+07 2.3E+07 1417704-35-8 C35H46N6O6S678.853 CALSXGHSUKIJHM-GCIMQLSOSA-N3.516 2 0 =O)N[C@@H](C[C@@H ]1CCNC1=O)C(=O)C1=N C2=CC=CC=C2S1

(1-{3-methyl-1-[2-oxo-1-(2- CC(C)C[C@H](NC(=O)[C oxo-pyrrolidin-3- @H](CC1=CC=CC2=C1C ylmethyl)ethylcarbamoyl]b =CC=C2)NC(=O)OCC1=C 2.4E+07 2.4E+07 C34H40N4O6 600.715 UULYLRNRQOWCOR-ZHTHUIBPSA-N4.738 3 0 C=CC=C1)C(=O)N[C@@ utylcarbamoyl}-2- H](C[C@@H]1CCNC1=O naphthalen-1-yl- )C=O ethyl)carbamic acid benzyl ester

CN(C)C1=CC=C(C=C1)C( =O)N[C@@H](CC1=CC= 1E+07 1E+07 C24H23ClN4O4466.924 NBBWJEWPUKPHPZ-QFIPXVFZSA-N4.859 4 2 CC=C1)C(=O)NC1=C(Cl)C =C(C=C1)N(=O)=O

ClC1=CC(OC(=O)C2=CC3 =C(O2)C=CC=C3)=CN=C 1.1E+07 1.1E+07 C14H8ClNO3 273.675 QHBWMDVARYUYJW-UHFFFAOYSA-N2.95 4 2 1

ClC1=CC(OC(=O)C2=CC3 =C(O2)C=CC=C3)=CN=C 1.1E+07 1.1E+07 C14H8ClNO3 273.675 QHBWMDVARYUYJW-UHFFFAOYSA-N2.95 4 2 1 ClC1=CC(OC(=O)C2=CC3 =C(O2)C=CC=C3)=CN=C 1.1E+07 1.1E+07 C14H8ClNO3 273.675 QHBWMDVARYUYJW-UHFFFAOYSA-N2.95 4 2 1

ClC1=CN=CC(OC(=O)C2 1.1E+07 1.1E+07 C14H8ClNO2S 289.742 MNUHXGJUYTWVLU-UHFFFAOYSA-N3.294 4 2 =CC3=CC=CC=C3S2)=C1

ClC1=CN=CC(OC(=O)C2 1.1E+07 1.1E+07 C9H5ClN2O2S 240.67 CSEAAOWXHPFATP-UHFFFAOYSA-N1.798 4 2 =CSC=N2)=C1

COC1=CC(=CC=C1)C(=O) 1.1E+07 1.1E+07 C13H10ClNO3 263.68 UIXQHURPUVBNCZ-UHFFFAOYSA-N2.809 4 2 OC1=CC(Cl)=CN=C1

CC(C)C[C@H](NC(=O)[C @H](CC1=CC=CC2=C1C =CC=C2)NC(=O)OCC1=C 2.4E+07 2.4E+07 C38H47N5O7 685.82 GCYUVLWAEVVUEN-MCEBTLFFSA-N4.651 2 0 C=CC=C1)C(=O)N[C@@ H](C[C@@H]1CCNC1=O )C(=O)C(=O)NC(C)C

2-((4- ClC1=CC=C(SSC2=NC=C 3.1E+07 3.1E+07 C10H7ClN2S2 254.764 SPHGDOQAQWNVCF-UHFFFAOYSA-N2.89 4 2 C=N2)C=C1 chlorophenyl)disulfanyl)py rimidine

2-((4- BrC1=CC=C(SSC2=NC=C 3.1E+07 3.1E+07 C10H7BrN2S2 299.215 OAGXVFKPJKFNDS-UHFFFAOYSA-N3.066 4 2 C=N2)C=C1 bromophenyl)disulfanyl)py rimidine

2-((4- ClC1=CC=C(SSC2=NN=C 3.1E+07 3.1E+07 C8H5ClN2OS2 244.725 YANPJRMMERZAJG-UHFFFAOYSA-N4.021 4 2 O2)C=C1 chlorophenyl)disulfanyl)- 1,3,4-oxadiazole 4,6-dimethyl-2-((2- CC1=CC(C)=NC(SSC2=CC 3.1E+07 3.1E+07 C12H11N3O2S2293.37 OXOOBQWVUHEGBI-UHFFFAOYSA-N2.79 4 2 =CC=C2N(=O)=O)=N1 nitrophenyl)disulfanyl)pyri midine

(1R,2S,3S,5R)-3-(6-amino- 9H-purin-9-yl)-4,4-difluoro- NC1=C2N=CN([C@H]3[C 5- @H](O)[C@H](O)[C@@ 3.5E+07 3.5E+07 C11H13F2N5O3301.253 XSXKATMUCWUUFZ-JBBNEOJLSA-N-0.288 4 2 H](CO)C3(F)F)C2=NC=N (hydroxymethyl)cyclopent 1 ane-1,2-diol; 6',6'- difluoroaristeromycin

BrC1=CC=CC2=C1N(CC1 =CC3=C(S1)C=CC=C3)C( 1E+07 1E+07 C17H10BrNO2S372.242 UFOWXDUBQLPEOX-UHFFFAOYSA-N3.635 4 2 =O)C2=O

N-((S)-1-((S)-1-formyl-2- CC(C)C[C@H](NC(=O)C1 ((S)-2-oxopyrrolidin-3- =CC2=CC=CC=C2N1)C(= 1.3E+07 1.3E+07 C22H28N4O4 412.489 HXJZYYCILNIXEI-BQFCYCMXSA-N2.331 4 1 O)N[C@@H](C[C@@H] yl)ethylcarbamoyl)-3- 1CCNC1=O)C=O methylbutyl)-1H-indole-2- carboxamide

CC(C)C[C@H](NC(=O)[C N-[(benzyloxy)carbonyl]-L- @@H](NC(=O)OCC1=CC valyl-N1-{1-formyl-2-[(3S)- =CC=C1)C(C)C)C(=O)NC( 1.5E+07 1.5E+07 C26H38N4O6 502.611 RUHYGYHBVKWREW-UZVDJONISA-N2.682 3 0 C[C@@H]1CCNC1=O)C= 2-oxopyrrolidin-3-yl]ethyl}- O L-leucinamide

N-[(benzyloxy)carbonyl]-L- CC(C)C[C@H](NC(=O)[C @@H](NC(=O)OCC1=CC valyl-N1-((1S)-2-hydroxy-1- =CC=C1)C(C)C)C(=O)N[C 1.5E+07 1.5E+07 890648-83-6 {[(3S)-2-oxopyrrolidin-3- C26H40N4O6 504.627 GLZAWCKOCLSXEU-CMOCDZPBSA-N2.111 3 0 @H](CO)C[C@@H]1CCN yl]methyl}ethyl)-L- C1=O leucinamide

[Bi+3].[O- ]N(=O)=O.COC1=CC(=CC (OC)=C1OC)C1=C2[N- ]C(\C=C/2)=C(/C2=N/C(/ C=C2)=C(\C2=CC=C([N- 1.6E+07 1.6E+07 Bi*C56H52N4O12*NO31244.03 GUVHQKNLOYUAJE-FROCSNILSA-N1 0 ]2)/C(=C2/C=CC\1=N/2) C1=CC(OC)=C(OC)C(OC) =C1)C1=CC(OC)=C(OC)C (OC)=C1)C1=CC(OC)=C( OC)C(OC)=C1

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)COC1=CC =CC=C1)C(C)C)C(=O)N[C 2.3E+07 2.3E+07 1383922-52-8 C33H41N5O6S635.784 APIXGBAHHCHXMO-WWZJJOFDSA-N3.307 3 0 @@H](C[C@@H]1CCNC 1=O)C(=O)C1=NC2=CC= CC=C2S1

COC1=CC=CC(OCC(=O)N [C@@H](C(C)C)C(=O)N[ C@@H](CC(C)C)C(=O)N[ 2.3E+07 2.3E+07 1383922-88-0 C34H43N5O7S665.811 IWZSFDORUMHIJN-KXDOSHFCSA-N3.222 3 0 C@@H](C[C@@H]2CCN C2=O)C(=O)C2=NC3=CC =CC=C3S2)=C1

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)COC1=CC =C(O)C=C1)C(C)C)C(=O) 2.3E+07 2.3E+07 1359941-94-8 C33H41N5O7S651.784 ORLPJQUZUWTHRB-QIBSBUDHSA-N2.901 3 0 N[C@@H](C[C@@H]1C CNC1=O)C(=O)C1=NC2= CC=CC=C2S1 CC(C)C[C@H](NC(=O)[C @@H](NC(=O)COC1=CC =C(C=C1)N(C)C)C(C)C)C( 2.3E+07 2.3E+07 1383923-00-9 C35H46N6O6S678.853 VEMALIBHQMNWOA-GCIMQLSOSA-N3.516 2 0 =O)N[C@@H](C[C@@H ]1CCNC1=O)C(=O)C1=N C2=CC=CC=C2S1

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)COC1=CC =CN=C1)C(C)C)C(=O)N[C 2.3E+07 2.3E+07 1383922-92-6 C32H40N6O6S636.772 VOKLNKGFAWURBK-GGHZGINBSA-N2.055 2 0 @@H](C[C@@H]1CCNC 1=O)C(=O)C1=NC2=CC= CC=C2S1

CC(C)C[C@H](NC(=O)[C @@H](NC(=O)CNC1=CC =CC=C1)C(C)C)C(=O)N[C 2.3E+07 2.3E+07 1383922-55-1 C33H42N6O5S 634.8 PPHLPUPOOAKMQM-WWZJJOFDSA-N3.038 2 0 @@H](C[C@@H]1CCNC 1=O)C(=O)C1=NC2=CC= CC=C2S1

tert-butyl 4-({[(S)-4-methyl- 1-oxo-1-({(S)-1-oxo-3-[(S)-2- CC(C)C[C@H](NC(=O)OC oxopyrrolidin-3-yl]propan- 1CCN(CC1)C(=O)OC(C)(C 3.2E+07 3.2E+07 C24H40N4O7 496.604 SBHUNCJSGGMNPS-LNLFQRSKSA-N2.275 3 0 )C)C(=O)N[C@@H](C[C 2-yl}amino)pentan-2- @@H]1CCNC1=O)C=O yl]carbamoyl}oxy)piperidin e-1-carboxylate

4-benzyl-1- (methylsulfonyl)piperidin- CC(C)C[C@H](NC(=O)OC 1(CC2=CC=CC=C2)CCN( 4-yl {(S)-4-methyl-1-oxo-1- CC1)S(C)(=O)=O)C(=O)N 3.2E+07 3.2E+07 [{(S)-1-oxo-3-[(S)-2- C27H40N4O7S564.703 ZLOZUJAXLMKVNG-VABKMULXSA-N2.471 2 0 [C@@H](C[C@@H]1CC oxopyrrolidin-3-yl]propan- NC1=O)C=O 2-yl}amino]pentan-2- yl}carbamate

sodium (2S)-2-{(S)-2-[({[4- benzyl-1- [Na+].CC(C)C[C@H](NC( (methylsulfonyl)piperidin- =O)OC1(CC2=CC=CC=C2 4-yl]oxy}carbonyl)amino]-4- )CCN(CC1)S(C)(=O)=O)C( 3.2E+07 3.2E+07 C27H41N4O10S2*Na668.765 PVFOFJYHUDKJAA-FLABFKKQSA-M0.467 2 0 =O)N[C@@H](C[C@@H methylpentanamido}-1- ]1CCNC1=O)C(O)S([O- ])(=O)=O hydroxy-3-[(S)-2- oxopyrrolidin-3-yl]propane- 1-sulfonate

CCCC[C@H](NC(=O)[C@ H](CCC(O)=O)NC(=O)[C @H](CC1=CC=C(O)C=C1 )NC(=O)[C@@H](NC(=O )[C@H](CC(C)C)NC(=O)[ C@H](CC(O)=O)NC(=O)[ C@H](CC(C)C)NC(C)=O)[ C@@H](C)O)C(=O)N[C @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 C119H191N25O352531.97 FTNDXEAVLOXOEU-WPJBOECXSA-N1.123 1 0 @@H](CO)C(=O)N[C@ @H](CC(C)C)C(=O)N[C@ @H](CCC(N)=O)C(=O)N[ C@@]1(C)CCCC=CCCC[C @](C)(NC(=O)[C@H](CC CCN)NC(=O)[C@@H](N C(=O)[C@@H](NC1=O)C CSCC[C@H](NC(=O)[C@(C)C)C(C)C)C(=O)N[C@ H](CCC(O)=O)NC(=O)[C @H](CC1=CC=C(O)C=C1 )NC(=O)[C@@H](NC(=O )[C@H](CC(C)C)NC(=O)[ C@H](CC(O)=O)NC(=O)[ C@H](CC(C)C)NC(C)=O)[ C@@H](C)O)C(=O)N[C @@H](CC(C)C)C(=O)N[C 3.3E+07 3.3E+07 C118H189N25O35S2550.01 XJXOKQDAPSDNJV-MXTOWPHFSA-N0.598 1 0 @@H](CO)C(=O)N[C@ @H](CC(C)C)C(=O)N[C@ @H](CCC(N)=O)C(=O)N[ C@@]1(C)CCCC=CCCC[C @](C)(NC(=O)[C@H](CC CCN)NC(=O)[C@@H](N C(=O)[C@@H](NC1=O)C (C)C)C(C)C)C(=O)N[C@