Mitigating the Inhibition of Human Bile Salt Export Pump by Drugs

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Mitigating the inhibition of human Bile Salt Export Pump by drugs: opportunities provided by physicochemical property modulation, in-silico modeling and structural modification

Daniel J. Warner, Hongming Chen, Louis-David Cantin, J. Gerry Kenna, Simone Stahl, Clare L. Walker, Tobias Noeske Drug Metabolism and Disposition

Supplemental Data

Table S4. Complete list of all compounds used for this study.

BSEP Mean Compound Name SMILES IC50 (µM) ClogP MW Data Set Ion Class Class 1,3-BIS( 2-CHLOROETHYL)-N- 97.21 1.316 214.1 Test Neutral POS NITROSOUREA C(CCl)NC(=O)N(CCCl)N=O 4-AMINO BUTYLBENZOATE 181.1 2.981 193.2 Train Neutral POS CCCCOC(=O)c1ccc(cc1)N 4-CHLORO-3,5- 129.9 3.483 156.6 Train Acid POS DIMETHYLPHENOL Cc1cc(cc(c1Cl)C)O 5-FLUOROURACIL c1c(c(=O)[nH]c(=O)[nH]1)F >1000 -0.577 130.1 Test Neutral NEG 8-HYDROXY QUINOLINE c1cc2cccnc2c(c1)O >1000 2.077 145.2 Train Neutral NEG A-967079 CC/C(=N\O)/C(=C/c1ccc(cc1)F)/C 26.81 3.536 207.2 Train Neutral POS ACEPROMAZINE CC(=O)c1ccc2c(c1)N(c3ccccc3S2)CC 111.6 4.18 326.5 Test Base POS CN(C)C ACETAMINOPHEN CC(=O)Nc1ccc(cc1)O >1000 0.494 151.2 Train Neutral NEG ACETANILIDE CC(=O)Nc1ccccc1 >1000 1.161 135.2 Test Neutral NEG ACETARSONE >1000 -1.363 275.1 Train Acid NEG CC(=O)Nc1cc(ccc1O)[As](=O)(O)O ACETYL CHOLINE CC(=O)OCC[N+](C)(C)C >1000 -3.467 146.2 Train Cationic NEG ACNECLEAR c1cc(c(cc1Cl)Cl)COC(Cn2ccnc2)c3ccc <10 5.812 416.1 Train Base POS (cc3Cl)Cl ACTARIT CC(=O)Nc1ccc(cc1)CC(=O)O >1000 0.433 193.2 Test Acid NEG ACYCLOVIR c1nc2c(=O)[nH]c(nc2n1COCCO)N >1000 -2.422 225.2 Train Neutral NEG ADENINE c1[nH]c2c(ncnc2n1)N >1000 -0.148 135.1 Train Neutral NEG ADIPHENINE CCN(CC)CCOC(=O)C(c1ccccc1)c2cc 158.4 4.525 311.4 Train Base POS ccc2 ALBUTEROL >1000 0.061 239.3 Train Base NEG CC(C)(C)NCC(c1ccc(c(c1)CO)O)O ALMOKALANT CCCS(=O)CCCN(CC)CC(COc1ccc(cc 55.75 2.213 352.5 Train Base POS 1)C#N)O ALPHA-METHYLDOPA >1000 -2.264 211.2 Test Zwitterion NEG C[C@](Cc1ccc(c(c1)O)O)(C(=O)O)N ALPIDEM CCCN(CCC)C(=O)Cc1c(nc2n1cc(cc2) 9.155 5.581 404.3 Test Neutral POS Cl)c3ccc(cc3)Cl ALTRETAMINE CN(C)c1nc(nc(n1)N(C)C)N(C)C >1000 1.665 210.3 Train Neutral NEG Erlotinib COCCOc1cc2c(cc1OCCOC)ncnc2Nc3 <10 4.342 393.4 Train Neutral POS cccc(c3)C#C AMILORIDE >1000 -2.222 229.6 Test Base NEG c1(c(nc(c(n1)Cl)N)N)C(=O)NC(=N)N AMINOGLUTETHIMIDE >1000 0.766 232.3 Test Neutral NEG CCC1(CCC(=O)NC1=O)c2ccc(cc2)N AMINOHIPPURIC ACID c1cc(ccc1C(=O)NCC(=O)O)N >1000 -0.253 194.2 Train Acid NEG AMIODARONE CCCCc1c(c2ccccc2o1)C(=O)c3cc(c(c( <10 8.945 645.3 Test Base POS c3)I)OCCN(CC)CC)I AMLODIPINE CCOC(=O)C1=C(NC(=C(C1c2ccccc2 16 3.434 408.9 Train Base POS Cl)C(=O)OC)C)COCCN AMODIAQUINE CCN(CC)Cc1cc(ccc1O)Nc2ccnc3c2cc 77.76 5.465 355.9 Train Base POS c(c3)Cl AMOXAPINE c1ccc2c(c1)N=C(c3cc(ccc3O2)Cl)N4C 230.1 3.406 313.8 Test Base POS CNCC4 AMRINONE c1cnccc1c2cc(c(=O)[nH]c2)N 370.8 -0.689 187.2 Train Neutral NEG ANTAZOLINE >1000 4.112 265.4 Train Base NEG c1ccc(cc1)CN(CC2=NCCN2)c3ccccc3 ANTIPYRINE Cc1cc(=O)n(n1C)c2ccccc2 >1000 0.204 188.2 Train Neutral NEG APOMORPHINE CN1CCc2cccc- 211.5 2.49 267.3 Train Base POS 3c2[C@H]1Cc4c3c(c(cc4)O)O ARC 68475AA c1ccc(cc1)CCOCCS(=O)(=O)NCCNC 35.69 2.523 465.6 Test Base POS Cc2ccc(c3c2sc(=O)[nH]3)O ARECOLINE CN1CCC=C(C1)C(=O)OC >1000 0.903 155.2 Train Base NEG ARH047108 CCc1cccc(c1CNc2cc(cn3c2nc(c3C)C) <10 3.997 336.4 Test Neutral POS C(=O)N)C ARM 390 CCN(CC)C(=O)c1ccc(cc1)C(=C2CCN 105.8 3.529 348.5 Train Base POS CC2)c3ccccc3 Sorafenib CNC(=O)c1cc(ccn1)Oc2ccc(cc2)NC(= <10 5.455 464.8 Test Neutral POS O)Nc3ccc(c(c3)C(F)(F)F)Cl Dexamethasone C[C@@H]1C[C@H]2[C@@H]3CCC4 101.7 1.785 392.5 Train Neutral POS =CC(=O)C=C[C@@]4([C@]3([C@H]( C[C@@]2([C@]1(C(=O)CO)O)C)O)F) C ASPARTAME COC(=O)[C@H](Cc1ccccc1)NC(=O)[C >1000 -2.135 294.3 Train Zwitterion NEG @H](CC(=O)O)N ASTEMIZOLE COc1ccc(cc1)CCN2CCC(CC2)Nc3nc4 <10 5.837 458.6 Train Base POS ccccc4n3Cc5ccc(cc5)F AZ1 c1ccc(c(c1)C(=O)NCC(=O)O)N >1000 0.347 194.2 Train Acid NEG AZ10 Cc1ccc(cc1n2cnc3ccc(cc3c2=O)N4C <10 3.403 539.6 Train Base POS CN(CC4)C)NC(=O)c5ccnc(c5)N6CCO CC6 AZ100 CC[C@@H](c1ccccc1)NC(=O)c2c3cc <10 7.385 382.5 Train Acid POS ccc3nc(c2O)c4ccccc4 AZ101 CC1(O[C@@H]2CO[C@@]3([C@H]([ >1000 0.042 339.4 Train Neutral NEG C@@H]2O1)OC(O3)(C)C)COS(=O)(= O)N)C AZ102 16.42 2.411 376.5 Train Neutral POS C[C@@H]1C[C@H]2[C@@H]3CCC4 =CC(=O)C=C[C@@]4([C@]3([C@H]( C[C@@]2([C@H]1C(=O)CO)C)O)F)C AZ103 CCCC(=O)OCOC(=O)C1=C(NC(=C(C 36.35 5.53 456.3 Train Neutral POS 1c2cccc(c2Cl)Cl)C(=O)OC)C)C AZ104 CN1[C@@H]2C[C@H](C[C@H]1[C@ >1000 0.29 303.4 Test Base NEG H]3[C@@H]2O3)OC(=O)[C@H](CO)c 4ccccc4 AZ105 CCOC(=O)C(CCc1ccccc1)NC2CCc3c 74.86 1.824 424.5 Train Zwitterion POS cccc3N(C2=O)CC(=O)O AZ106 CN(C)c1c2c(ncn1)n(cn2)C3C(C(C(O3) >1000 -1.245 294.3 Train Base NEG CO)N)O AZ107 >1000 0.119 341.4 Train Neutral NEG CCCSc1nc(c2c(n1)n(cn2)[C@H]3[C@ @H]([C@@H]([C@H](O3)CO)O)O)N AZ108 CCC(=O)OC(C(C)C)OP(=O)(CCCCc1 <13.34 7.445 563.7 Test Acid POS ccccc1)CC(=O)N2CC(CC2C(=O)O)C3 CCCCC3 AZ109 Cc1c(c(n[nH]1)C)Cc2c(c3c(=O)n(c(=O 247.8 2.577 461.5 Test Neutral POS )n(c3s2)CC(C)C)C)C(=O)N4C[C@@H ](CO4)O AZ11 <12.85 1.929 478.9 Train Neutral POS C[C@@](C(=O)Nc1ccc(cc1Cl)S(=O)(= O)c2ccc(cc2)C(=O)N(C)C)(C(F)(F)F)O AZ110 Cc1c(c(n[nH]1)C)Cc2c(c3c(=O)n(c(=O 703 1.958 447.5 Test Neutral NEG )n(c3s2)C(C)C)C)C(=O)N4C[C@@H]( CO4)O AZ111 Cc1cc(on1)c2ccc(cc2F)N3C[C@@H]( >1000 1.017 343.3 Train Neutral NEG OC3=O)Cn4ccnn4 AZ112 >1000 -4.226 344.3 Test Neutral NEG C([C@@H]1[C@@H]([C@@H]([C@H ]([C@@H](O1)O[C@H]([C@@H](CO) O)[C@@H]([C@H](CO)O)O)O)O)O)O AZ113 c1ccc(c(c1)C(=O)NCCCCCCCC(=O)O >750.9 3.24 279.3 Test Acid NEG )O AZ114 CCOCCNS(=O)(=O)c1ccc(cc1)Nc2ncc <10 3.228 444.6 Train Neutral POS c(n2)c3cnc(n3C(C)C)C AZ115 COC(=O)NN=Cc1c[n+](c2ccccc2[n+]1[ >939.8 -1.839 262.2 Train Neutral NEG O-])[O-] AZ116 c1ccc(cc1)CCOCCCS(=O)(=O)CCCN 32.35 2.665 478.6 Train Base POS CCc2ccc(c3c2sc(=O)[nH]3)O AZ117 16.26 3.168 488.4 Test Neutral POS Cc1nc(c(n1Cc2c(c3c(=O)n(c(=O)n(c3s 2)CC(C)C)C)C(=O)N(C)OC)Cl)Cl AZ118 CNC[C@@H](Cc1ccc(c(c1)C(=O)NCC 133.2 4.008 391 Train Base POS 23CC4CC(C2)CC(C4)C3)Cl)O AZ119 c1cc(cnc1)CC[C@H](COc2ccc(cc2)c3 >1000 2.111 404.5 Test Neutral NEG ccc(s3)S(=O)(=O)N)O AZ12 Cc1ccc(cc1NC(=O)c2cccc(c2)CN3CC <10 5.259 532.6 Train Base POS N(CC3)C)NC(=O)c4cccc5c4oc6c5cccc 6 AZ120 59.51 3.937 437.6 Train Base POS Cc1ccc(cc1NC(=O)CC23CC4CC(C2)C C(C4)C3)C(=O)N5CC6CNCC(C5)O6 AZ121 Cc1ccc2c(c1)c(c(n2CC(=O)O)C)c3ccn <10 5.006 344.4 Train Acid POS c4c3cccc4C AZ122 19.09 2.696 413.9 Train Neutral POS c1ccc2c(c1)CC(C(=O)N2C[C@H](CO) O)NC(=O)c3cc4cc(ccc4[nH]3)Cl AZ123 164 0.888 654.8 Train Neutral POS CCCCCC(C1C(CC(CC(CC(CC(CC(CC (/C(=C/C=C/C=C/C=C/C=C/C(C(OC1= O)C)O)/C)O)O)O)O)O)O)O)O AZ124 CCCc1ncc(n1CC)c2ccnc(n2)Nc3ccc(c <10 3.588 444.6 Test Neutral POS c3)S(=O)(=O)NCCOC AZ125 CCc1ncc(n1C(C)C)c2ccnc(n2)Nc3ccc( <10 3.368 444.6 Train Neutral POS cc3)S(=O)(=O)NCCOC AZ126 Cc1ccc2c(c1)c(c(n2CC(=O)O)C)c3ccn <10 5.489 398.4 Train Acid POS c4c3cccc4C(F)(F)F AZ127 <10.95 2.402 419.9 Train Neutral POS c1ccc2c(c1)CC(C(=O)N2C[C@H](CO) O)NC(=O)c3cc4cc(sc4[nH]3)Cl AZ128 Cc1ccc2c(c1)c(c(n2CC(=O)O)C)c3ccn <10 5.271 364.8 Train Acid POS c4c3cccc4Cl AZ129 CN1[C@@H]2CC[C@H]1C[C@H](C2) 188.6 3.52 307.4 Train Base POS OC(c3ccccc3)c4ccccc4 AZ13 c1cc(c(cc1Cn2c3ccsc3cc2C(=O)O)Cl) 13.72 5.233 326.2 Train Acid POS Cl AZ130 C[C@@H](CN1c2ccccc2Sc3c1cc(cc3) 127 4.831 328.5 Test Base POS OC)CN(C)C AZ131 c1cc(ccc1c2ccc(o2)/C=N/N3CC(=O)N 145.5 1.631 314.3 Test Neutral POS C3=O)[N+](=O)[O-] AZ132 C[C@H]([C@@H]1[C@H]2CC(=C(N2 >1000 -1.353 299.3 Train Zwitterion NEG C1=O)C(=O)O)SCCNC=N)O AZ133 CN1CCC[C@H]1c2cccnc2 >1000 0.883 162.2 Train Base NEG AZ134 <10 2.21 455.5 Train Neutral POS c1ccc(cc1)C2=C(C(=O)N(C2=O)Cc3cc c(nc3)N)Nc4ccc(cc4)N5CCOCC5 AZ135 CC(C)(CO)[C@H](C(=O)NCCCO)O >1000 -1.648 205.3 Test Neutral NEG AZ136 CCCSc1nc(c2c(n1)n(cn2)[C@H]3[C@ >1000 0.391 648.2 Train Acid NEG @H]([C@@H]([C@H](O3)COP(=O)(O )OP(=O)(C(P(=O)(O)O)(Cl)Cl)O)O)O) N AZ137 C[C@H](CO)NCCCc1ccc(c(c1)C(=O) 65.56 4.916 419 Test Base POS NCC23CC4CC(C2)CC(C4)C3)Cl AZ138 CC(C)(C)NC[C@H](c1ccc(c(c1)CO)O) >1000 0.061 239.3 Train Base NEG O AZ139 CC(=O)Nc1ccccc1OC[C@](C)(CNC2C 71.54 2.285 446 Train Base POS CN(CC2)Cc3ccc(cc3)Cl)O AZ14 c1cc(c(cc1Cn2c3ccc(cc3cc2C(=O)O) 18.49 4.977 369.7 Train Acid POS O)C(F)(F)F)Cl AZ140 CC(=O)Nc1ccccc1OC[C@H](CNC2C 55.57 1.886 432 Test Base POS CN(CC2)Cc3ccc(cc3)Cl)O AZ141 CC[C@@H]1[C@@]([C@@H]([C@H] <12.88 2.374 748 Train Base POS (C(=O)[C@@H](C[C@]([C@@H]([C@ H]([C@H]([C@H](C(=O)O1)C)O[C@H] 2C[C@@]([C@H]([C@@H](O2)C)O)( C)OC)C)O[C@H]3[C@@H]([C@H](C[ C@H](O3)C)N(C)C)O)(C)OC)C)C)O)( C)O AZ142 CS(=O)(=O)Oc1ccc(cc1)OCCc2ccc(cc <13.36 4.823 516.6 Train Acid POS 2)C[C@@H](C(=O)O)SCCc3ccc(cc3) O AZ143 <10 1.262 469 Test Neutral POS c1cnc(nc1)CCC[C@@H](CS(=O)(=O) N2CCN(CC2)c3ccc(cn3)Cl)N(C=O)O AZ144 CC(=O)OC1C(Sc2ccccc2N(C1=O)CC 82.02 3.647 414.5 Test Base POS N(C)C)c3ccc(cc3)OC AZ145 <10 4.45 310.4 Train Neutral POS C[C@]12CC[C@@H]3c4ccc(cc4CC[C @H]3[C@@H]1CC[C@]2(C#C)O)OC AZ146 >1000 -6.523 615.6 Test Base NEG C1[C@H]([C@@H]([C@H]([C@@H]([ C@H]1N)O[C@@H]2[C@@H]([C@H] ([C@@H]([C@H](O2)CO)O)O)N)O[C @H]3[C@@H]([C@@H]([C@H](O3)C O)O[C@@H]4[C@@H]([C@H]([C@@ H]([C@@H](O4)CN)O)O)N)O)O)N AZ147 C[C@H]1C[C@H]2[C@@H]3CC[C@ 33.03 1.742 374.5 Train Neutral POS @]([C@]3(C[C@@H]([C@@H]2[C@ @]4(C1=CC(=O)C=C4)C)O)C)(C(=O) CO)O AZ148 C[C@H]1[C@@H]([C@H]([C@H]([C >1000 -1.901 584.7 Train Neutral NEG @@H](O1)O[C@H]2C[C@H]([C@@] 3([C@@H]4[C@@H](CC[C@@]3(C2) O)[C@]5(CC[C@@H]([C@]5(C[C@H] 4O)C)C6=CC(=O)OC6)O)CO)O)O)O) O AZ149 CCCCC[C@@H](/C=C/[C@H]1[C@@ >1000 2.013 352.5 Test Acid NEG H](CC(=O)[C@@H]1C/C=C\CCCC(=O )O)O)O AZ15 CCCC(c1ccccc1)(c2ccccc2)C(=O)OC <13.19 5.982 353.5 Test Base POS CN(CC)CC AZ150 C[C@]12C[C@@H]([C@]3(C(C1C[C 235.6 0.708 394.4 Train Neutral POS @H]([C@@]2(C(=O)CO)O)O)CCC4= CC(=O)C=C[C@@]43C)F)O AZ151 CCS(=O)(=O)c1ccc(c(c1)F)c2cc(ccc2 168.3 2.718 372.8 Test Acid POS OCC(=O)O)Cl AZ152 C[C@]12CC[C@H]3[C@H]([C@@H]1 <10 3.927 337.5 Train Neutral POS CC[C@]2(C#C)O)CCC4=Cc5c(cno5)C [C@]34C AZ153 <27.03 3.71 408.9 Train Base POS C[C@H](CC(=O)Nc1c2ccc(nc2ccc1Cl) N3CC[C@@H](C3)N)c4ccccc4 AZ154 234.8 2.959 404.4 Train Acid POS c1ccc(cc1)C(=O)N[C@@H](Cc2ccc(cc 2)O)C(=O)Nc3ccc(cc3)C(=O)O AZ155 c1cc(nc2c1c(c(cc2)Cl)C(=O)NCC3CC 106.9 3.489 386.9 Train Base POS CCC3)N4CC[C@@H](C4)N AZ156 c1ccc(c(c1)CCNC(=O)c2cc(ccc2Cl)n3 34.42 3.686 405.2 Train Neutral POS c(=O)[nH]c(=O)cn3)Cl AZ157 Cc1c(c2c3c4c1O[C@@](C4=O)(O/C= <10 3.71 822.9 Test Zwitterion POS C/[C@@H]([C@H]([C@H]([C@@H]([ C@@H]([C@@H]([C@H]([C@H](/C= C/C=C(\C(=O)Nc(c2O)c(c3O)/C=N/N5 CCN(CC5)C)/C)C)O)C)O)C)OC(=O)C) C)OC)C)O AZ158 CCOC(=O)[C@H](CCc1ccccc1)N[C@ 15.5 1.736 438.5 Test Zwitterion POS @H](C)C(=O)N2Cc3ccccc3C[C@H]2C (=O)O AZ159 Cc1c(c(no1)c2c(cccc2Cl)Cl)C(=O)N[C <10 2.981 470.3 Train Acid POS @H]3[C@@H]4N(C3=O)[C@H](C(S4) (C)C)C(=O)O AZ16 <10 5.76 519.6 Train Base POS Cc1ccc(cc1n2cnc3ccc(cc3c2=O)N4C CN(CC4)C)NC(=O)c5cccc(c5)c6ccco6 AZ160 C[C@]1(c2cccc(c2C(=O)C3=C([C@]4( >1000 -1.78 444.4 Test Zwitterion NEG C(CC31)[C@@H](C(=C(C4=O)C(=O) N)O)N(C)C)O)O)O)O AZ161 CN1[C@@H]2CC[C@H]1C[C@H](C2) >1000 1.299 289.4 Test Base NEG OC(=O)C(CO)c3ccccc3 AZ162 CN1[C@@H]2CC[C@H]1C[C@H](C2) >1000 1.427 275.3 Test Base NEG OC(=O)C(c3ccccc3)O AZ163 CN1CCN(CC1)c2ccccc2C=C3C(=O)N <10 5.668 448.4 Train Base POS (CCS3)c4ccc(c(c4)Cl)Cl AZ164 >1000 -3.75 547.6 Train Zwitterion NEG CC(C)(C(=O)O)O/N=C(/c1csc(n1)N)\C (=O)N[C@H]2[C@@H]3N(C2=O)C(=C (CS3)C[n+]4ccccc4)C(=O)O AZ165 >1000 -7.138 685.7 Train Base NEG C1[C@@H](C(=O)N[C@H](C(=O)N[C @H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[ C@H](C(=O)N1)C2CC(NC(=N)N2)O)C O)CO)NC(=O)CC(CCCN)N AZ166 C[C@H]([C@@H]1[C@H]2CC(=C(N2 >1000 -1.353 299.3 Train Zwitterion NEG C1=O)C(=O)O)SCCNC=N)O AZ167 CC1[C@@]([C@H](C(O1)OC2C(C(C( >1000 -4.279 581.6 Train Base NEG C(C2O)O)NC(=N)N)O)NC(=N)N)OC3[ C@@H]([C@H]([C@@H]([C@H](O3) CO)O)O)NC)(C=O)O AZ168 c1ccc(cc1)[C@@H]2C[C@H]2N >1000 1.478 133.2 Test Base NEG AZ169 C[C@]1([C@H]2CC[C@H](C2)C1(C)C >1000 2.825 167.3 Train Base NEG )NC AZ17 C=CC1CN2CCC1CC2C(c3ccnc4c3cc >1000 2.49 294.4 Train Base NEG cc4)O AZ170 COC(=O)[C@H]1[C@H](CC[C@@H]2 254 2.171 354.4 Train Base POS [C@@H]1C[C@H]3c4c(c5ccccc5[nH] 4)CCN3C2)O AZ171 CN1[C@@H]2CC[C@H]1C[C@H](C2) >1000 1.299 289.4 Train Base NEG OC(=O)[C@H](CO)c3ccccc3 AZ172 CC[C@@H](CO)NC(=O)[C@H]1CN([ 33.07 2.224 353.5 Test Base POS C@@H]2Cc3cn(c4c3c(ccc4)C2=C1)C )C AZ173 C[N+]1([C@@H]2C[C@H](C[C@H]1[ >1000 -1.706 392.5 Test Cationic NEG C@H]3[C@@H]2O3)OC(=O)C(c4cccs 4)(c5cccs5)O)C AZ174 c1cc(c2c3c1C[C@@H]4[C@]5([C@]3( >1000 0.359 341.4 Train Base NEG CCN4CC6CC6)[C@@H](O2)C(=O)CC 5)O)O AZ175 c1c(c(=O)[nH]c(=O)n1[C@H]2C[C@@ >1000 -0.413 296.2 Train Neutral NEG H]([C@H](O2)CO)O)C(F)(F)F AZ176 C[C@H](CCC(=O)O)[C@H]1CC[C@ <10 4.514 392.6 Train Acid POS @H]2[C@@]1(CC[C@H]3[C@H]2[C @H](C[C@H]4[C@@]3(CC[C@H](C4) O)C)O)C AZ177 549 0.159 327.4 Train Base NEG C=CCN1CC[C@]23c4c5ccc(c4O[C@ H]2C(=O)CC[C@]3([C@H]1C5)O)O AZ178 <10 2.707 430.4 Train Neutral POS C[C@](CS(=O)(=O)c1ccc(cc1)F)(C(=O )Nc2ccc(c(c2)C(F)(F)F)C#N)O AZ179 Cc1cccc(c1NC(=O)[C@H]2CCCCN2C >1000 2.104 246.4 Test Base NEG )C AZ18 Cc1ccc(cc1NC(=O)c2cccc(c2)OC3CC <10 6.048 561.7 Test Base POS N(CC3)C(C)C)NC(=O)c4cccc5c4oc6c 5cccc6 AZ180 <10 3.341 470.5 Train Acid POS Cc1ccc(c(c1)[N+](=O)[O- ])OC(C)(C)[C@H]2OC[C@H]([C@H]( O2)c3cccnc3)C/C=C\CCC(=O)O AZ181 CCCCCC(C)(/C=C/[C@H]1[C@@H](C 328.7 2.67 368.5 Train Acid NEG [C@@H]([C@@H]1C/C=C\CCCC(=O) O)O)O)O AZ182 CC1=C(N2C([C@@H](C2=O)NC(=O) >1000 -1.727 349.4 Test Zwitterion NEG C(C3=CCC=CC3)N)SC1)C(=O)O AZ183 CC1([C@@H](N2[C@H](S1)[C@@H]( >1000 -1.872 365.4 Train Zwitterion NEG C2=O)NC(=O)[C@@H](c3ccc(cc3)O) N)C(=O)O)C AZ184 CC[C@@H]1[C@@]([C@@H]([C@H] >983.1 1.611 733.9 Train Base NEG (C(=O)[C@@H](C[C@@]([C@@H]([C @H]([C@@H]([C@H](C(=O)O1)C)O[C @H]2C[C@@]([C@H]([C@@H](O2)C )O)(C)OC)C)O[C@H]3[C@@H]([C@H ](C[C@H](O3)C)N(C)C)O)(C)O)C)C)O )(C)O AZ185 COc1ccc2c(c1)c(ccn2)[C@H](C3CC4 98.83 2.785 324.4 Train Base POS CCN3CC4C=C)O AZ186 CN(C)c1c2c(ncn1)n(cn2)C3[C@@H]([ >787.1 0.268 471.5 Test Base NEG C@@H]([C@H](O3)CO)NC(=O)C(Cc4 ccc(cc4)OC)N)O AZ187 C[C@]12C[C@@H]([C@H]3[C@H]([C 91.47 1.423 360.4 Train Neutral POS @@H]1CC[C@@]2(C(=O)CO)O)CCC 4=CC(=O)C=C[C@]34C)O AZ188 C[C@]12CCC(=O)C=C1CC[C@@H]3[ 251.7 1.887 362.5 Train Neutral POS C@@H]2[C@H](C[C@]4([C@H]3CC[ C@@]4(C(=O)CO)O)C)O AZ189 <10 3.864 296.4 Train Neutral POS C[C@]12CC[C@@H]3c4ccc(cc4CC[C @H]3[C@@H]1CC[C@]2(C#C)O)O AZ19 CC12CCN(C1N(c3c2cc(cc3)OC(=O)N >1000 1.95 275.4 Test Base NEG C)C)C AZ190 C[C@]12CC[C@H]3[C@H]([C@@H]1 17.06 3.44 330.5 Train Neutral POS CC[C@@H]2C(=O)CO)CCC4=CC(=O )CC[C@]34C AZ191 35.84 3.61 456.4 Test Acid POS C[C@@H](C(=O)O)Oc1ccc(cc1c2ccc( c(c2)C(F)(F)F)S(=O)(=O)C)C(F)(F)F AZ192 C=CC1=C(N2[C@@H]([C@@H](C2= >1000 0.252 453.5 Test Acid NEG O)NC(=O)/C(=N\OCC(=O)O)/c3csc(n3 )N)SC1)C(=O)O AZ193 c1c(n(c(=N)nc1N2CCCCC2)O)N >1000 -2.134 209.3 Train Neutral NEG AZ194 <10 4.732 847 Train Zwitterion POS Cc1c(c2c3c4c1O[C@@](C4=O)(O/C= C/[C@@H]([C@H]([C@H]([C@@H]([ C@@H]([C@@H]([C@H]([C@H](/C= C/C=C(\C(=O)NC(=C5C3=NC6(N5)CC N(CC6)CC(C)C)C2=O)/C)C)O)C)O)C) OC(=O)C)C)OC)C)O AZ195 c1ccc(cc1)OCCC[N+]23CCC(CC2)[C 127.1 2.341 484.7 Test Cationic POS @H](C3)OC(=O)C(c4cccs4)(c5cccs5) O AZ196 C[C@]12CC[C@H]3[C@H]([C@@H]1 18.46 2.97 298.4 Test Neutral POS CC[C@]2(C#C)O)CCC4=CC(=O)CC[C @H]34 AZ197 471.9 1.659 361.4 Train Neutral NEG C[C@@H](C(=O)N[C@H]1c2ccccc2C CN(C1=O)C)NC(=O)[C@H](C(C)C)O AZ198 196.6 4.116 470.5 Train Neutral POS CC1(C(=O)Nc2c(ccc(n2)Nc3c(cnc(n3) Nc4cc(c(c(c4)OC)OC)OC)F)O1)C AZ199 CCCCCCCCCCCCc1ccc(cc1)S(=O)(= 21.04 7.114 409.6 Train Acid POS O)Nc2nncs2 AZ2 c1ccc(c(c1)C(=O)O)S >1000 2.438 154.2 Train Acid NEG AZ20 CC[C@@H]1[C@@]([C@@H]([C@H] >1000 2.638 749 Train Base NEG (N(C[C@@H](C[C@@]([C@@H]([C@ H]([C@@H]([C@H](C(=O)O1)C)O[C@ H]2C[C@@]([C@H]([C@@H](O2)C)O )(C)OC)C)O[C@H]3[C@@H]([C@H]( C[C@H](O3)C)N(C)C)O)(C)O)C)C)C) O)(C)O AZ200 <10 6.058 487.9 Train Acid POS Cc1cc(cc(c1c2[nH]c3cc(ccc3n2)c4nnc (o4)Nc5cccc(c5)Cl)C)CCC(=O)O AZ201 COc1cccc(c1)N2C(=NC(=NC23CCCC >1000 1.408 287.4 Test Base NEG C3)N)N AZ21 c1ccc(cc1)CCC(CS(=O)(=O)N2CCN(C <10 3.651 435.5 Train Neutral POS C2)c3ccc(cc3)F)N(C=O)O AZ22 c1cnc(nc1)CCCC(CS(=O)(=O)N2CCN( <16.42 1.726 451.5 Train Neutral POS CC2)c3ccc(cc3)F)N(C=O)O AZ23 Cc1cccc(c1NC(=O)NC(=N)NC)C >1000 1.249 220.3 Train Base NEG AZ24 CC(=O)NC[C@H]1CN(C(=O)O1)c2ccc >1000 0.168 337.3 Train Neutral NEG (c(c2)F)N3CCOCC3 AZ25 c1cnc(nc1)CCC(CS(=O)(=O)N2CCN(C <10 0.733 454.9 Train Neutral POS C2)c3ccc(cn3)Cl)N(C=O)O AZ26 CN(C)C(=N)NC(=N)N >1000 -1.633 129.2 Test Base NEG AZ27 CN1CCc2cc3c(c(c2C1C4c5ccc(c(c5C( 23.91 2.27 413.4 Train Base POS =O)O4)OC)OC)OC)OCO3 AZ28 c1cnc(nc1)CCCC(CS(=O)(=O)N2CCC( <10 1.29 484 Train Neutral POS CC2)Oc3ccc(cn3)Cl)N(C=O)O AZ29 CC1(CC(CC(N1[O])(C)C)O)C >1000 0.949 172.2 Train Neutral NEG AZ3 <10 3.776 509.4 Train Neutral POS Cc1cc(ncn1)N2CCN(CC2)C(=O)N3CC N(CC3)S(=O)(=O)c4ccc(cc4)Br AZ30 c1ccc2c(c1)[nH]c(n2)c3[nH]c4ccccc4n 31.33 3.505 234.3 Train Neutral POS 3 AZ31 CCOc1cc(ccc1C(=O)OC)NC(=O)C 478.5 1.938 237.3 Train Neutral NEG AZ32 202.2 2.325 402.5 Train Acid POS CC(CCC(=O)O)C1CCC2C1(C(=O)CC 3C2C(=O)CC4C3(CCC(=O)C4)C)C AZ33 CC(C)(C)c1cc2c(=O)cc(oc2c(c1)C(C)( <10 4.952 302.4 Train Acid POS C)C)C(=O)O AZ34 c1ccc(cc1)CCC(CS(=O)(=O)N2CCN(C <10 3.303 435.5 Train Neutral POS C2)c3ccc(cc3)F)C(=O)NO AZ35 c1c(cc(cc1[N+](=O)[O-])[N+](=O)[O- 184.5 0.627 211.1 Train Neutral POS ])C(=O)N AZ36 CCOCn1cnc2c1c(=O)n(c(=O)n2C)CC 304.9 0.846 338.4 Train Neutral NEG CCC(C)(C)O AZ37 CC1CC2C3CC(C4=CC(=O)C=CC4(C3 33.56 2.522 434.5 Test Neutral POS C(CC2(C1(C(=O)COC(=O)C)O)C)O)C) F AZ38 c1cc2c(cc(n2Cc3ccc(c(c3)Cl)Cl)C(=O) <14.01 4.833 394.3 Test Acid POS O)c(c1)OCCCO AZ39 CCCc1ncc(c(n1)N)C[n+]2ccccc2C >1000 -3.891 243.3 Test Cationic NEG AZ4 c1cc(oc1)c2nc3nc(nc(n3n2)N)NCCN4 >1000 1.055 330.4 Train Base NEG CCOCC4 AZ40 Cc1cc2c([nH]1)ccc(c2F)Oc3c4cc(c(cc 22.73 5.835 464.5 Train Base POS 4ncn3)OCCCN5CCCCC5)OC AZ41 CN1CCc2cc3c(cc2C1C4c5ccc(c(c5C( 65.64 2.278 383.4 Train Base POS =O)O4)OC)OC)OCO3 AZ42 CNCC(c1cccc(c1)O)O >1000 -0.088 167.2 Train Base NEG AZ43 c1ccc(cc1)CCC(CS(=O)(=O)N2CCN(C <10 3.187 453 Train Neutral POS C2)c3ccc(cn3)Cl)N(C=O)O AZ44 CN1CCc2cccc- 390.9 2.49 267.3 Train Base NEG 3c2C1Cc4c3c(c(cc4)O)O AZ45 CC(CO)c1ccc2cc(ccc2c1)OC 97.58 2.825 216.3 Test Neutral POS AZ46 CC(C)(C)NCC(COc1c(nsn1)N2CCOC >1000 1.214 316.4 Train Base NEG C2)O AZ47 >1000 0.7 200.6 Train Neutral NEG c1cc(c(cc1[N+](=O)[O-])Cl)C(=O)N AZ48 CC(C)(C)NCC(COc1cccc2c1CC(C(C2) >1000 0.379 309.4 Train Base NEG O)O)O AZ49 c1cc(cnc1)CCC(CS(=O)(=O)N2CCN(C <10 1.69 453.9 Test Neutral POS C2)c3ccc(cn3)Cl)N(C=O)O AZ5 c1ccnc(c1)CCC(CS(=O)(=O)N2CCN(C <10 1.69 453.9 Test Neutral POS C2)c3ccc(cn3)Cl)N(C=O)O AZ50 CC(=O)Oc1ccc2c(c1)cc(n2Cc3ccc(c(c 55.21 4.742 378.2 Train Acid POS 3)Cl)Cl)C(=O)O AZ51 >1000 0.041 409.4 Train Neutral NEG CC(=O)NC[C@H]1CN(C(=O)O1)c2cc( c(c(c2)F)C3=CCN(CC3)C(=O)CO)F AZ52 Cc1cc2c(o1)cc(n2Cc3ccc(c(c3)Cl)Cl)C 15.89 5.219 324.2 Train Acid POS (=O)O AZ53 27.55 1.761 412.8 Train Neutral POS CC(=O)NC[C@H]1CN(C(=O)O1)c2ccc (cc2)C(=O)c3cnc4n3cc(cc4)Cl AZ54 CC(=O)NC[C@H]1CN(C(=O)O1)c2ccc 349.2 1.373 397.2 Train Neutral NEG (c(c2)F)n3cc(nc3)Br AZ55 c1cc(cnc1)CCC(CS(=O)(=O)N2CCC(C <10 1.718 469 Train Neutral POS C2)Oc3ccc(cn3)Cl)N(C=O)O AZ56 c1cc(c(cc1Cn2c(cc3c2ncs3)C(=O)O)C 22.39 4.172 327.2 Train Acid POS l)Cl AZ57 COc1c2cc(ccc2n(c1C(=O)O)Cc3ccc(c 39.57 4.428 366.2 Train Acid POS (c3)Cl)Cl)O AZ58 CN(Cc1cnc2c(n1)c(nc(n2)N)N)c3ccc(c >1000 -0.529 454.4 Train Acid NEG c3)C(=O)N[C@@H](CCC(=O)O)C(=O) O AZ59 Cc1cc([nH]n1)Nc2c(cnc(n2)NCc3cc(n <10 2.939 382.8 Train Neutral POS o3)c4ccccn4)Cl AZ6 c1cc(c(cc1Cn2c3ccc(cc3cc2C(=O)O) 49.84 4.887 336.2 Train Acid POS O)Cl)Cl AZ60 CCN(CC)C(=O)c1ccc(cc1)C(=C2CCN 86.07 3.672 366.5 Train Base POS CC2)c3cccc(c3)F AZ61 CCC1C(COC1=O)Cc2cncn2C >1000 -0.203 208.3 Train Base NEG AZ62 C[N+](C)(C)CC(CC(=O)O)O >1000 -4.767 162.2 Train Zwitterion NEG AZ63 CC(=CCC1C(O1)(C)C2C(C(CCC23CO 25.59 2.913 458.5 Train Acid POS 3)OC(=O)C=CC=CC=CC=CC(=O)O)O C)C AZ64 c1cc(oc1C=NN2CC(=O)NC2=O)[N+](= >1000 -0.467 238.2 Test Neutral NEG O)[O-] AZ65 CC(C)N=c1cc- 134.9 7.699 473.4 Train Neutral POS 2n(c3ccccc3nc2cc1Nc4ccc(cc4)Cl)c5c cc(cc5)Cl AZ66 CNC(=C[N+](=O)[O- >1000 0.67 314.4 Train Base NEG ])NCCSCc1ccc(o1)CN(C)C AZ67 161.3 1.909 245.3 Test Base POS CC(C(C)(C)C)NC(=NC#N)Nc1ccncc1 AZ68 >1000 0.19 252.3 Train Base NEG Cc1c(nc[nH]1)CSCCN=C(NC)NC#N AZ69 C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN >1000 -6.466 614.6 Train Base NEG )O)O)N)OC3C(C(C(O3)CO)OC4C(C(C (C(O4)CN)O)O)N)O)O)N AZ7 27.35 2.242 466.9 Train Neutral POS C[C@@](C(=O)Nc1ccc(cc1Cl)S(=O)(= O)c2ccc(cc2)NCCO)(C(F)(F)F)O AZ70 C[n+]1ccccc1C=NO >1000 -3.666 137.2 Test Cationic NEG AZ71 CCCCCCCCC=CCCCCCCCC(=O)OC <16.04 12.16 787.1 Train Zwitterion POS C(COP(=O)(O)OCC[N+](C)(C)C)OC(= O)CCCCCCCC=CCCCCCCCC AZ72 CCN(c1ccccc1C)C(=O)C=CC 109.5 3.429 203.3 Train Neutral POS AZ73 <10 6.379 510.6 Train Acid POS CCCc1c(ccc(c1O)C(=O)C)OCCCOc2c cc3c(=O)cc(oc3c2CCC)CCC(=O)O AZ74 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)C 606.4 4.429 286.3 Train Acid NEG CCC2 AZ76 CN(C)N=Nc1c(nc[nH]1)C(=O)N >1000 0.467 182.2 Train Neutral NEG AZ77 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >892.2 3.886 361.7 Test Acid NEG cc(n2)C(=O)O)Cl AZ78 c1cc(c(cc1[C@H](CN)O)O)O >1000 -0.989 169.2 Test Base NEG AZ79 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >1000 2.102 398.4 Train Acid NEG cc(n2)C(=O)O)N(C)C(=O)C AZ8 <10 4.081 481 Test Neutral POS c1cc(ccc1c2ccncc2)C(=O)N3CCN(CC 3)S(=O)(=O)c4cc5cc(ccc5[nH]4)Cl AZ80 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >1000 0.893 343.3 Train Acid NEG =O)cc([nH]2)C(=O)O AZ81 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >1000 2.031 344.3 Test Acid NEG =O)cc(o2)C(=O)O AZ82 CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( 364.7 4.055 395.3 Test Acid NEG cc(n2)C(=O)O)C(F)(F)F AZ83 CC1=C([C@H](C(=C(N1)C)C(=O)OC( <10 3.916 371.4 Train Neutral POS C)C)c2cccc3c2non3)C(=O)OC AZ84 23.03 4.093 265.3 Train Neutral POS COc1ccc(cc1)Nc2ccn(n2)c3ccccc3 AZ85 Cc1cccc(c1S(=O)c2[nH]c3ccccc3n2)c <10 3.758 363.4 Test Neutral POS 4cc(ccn4)OC AZ86 Cc1cc(cc(c1OC(=O)C)C)Nc2ccn(n2)c <10 4.521 321.4 Train Neutral POS 3ccccc3 AZ87 CCc1cc(c2c(c1O)c(=O)cc(o2)C(=O)O) 111.7 3.903 262.3 Train Acid POS CC AZ88 CCCc1ccc(c2c1oc(cc2=O)C(=O)O)OC 270.6 2.335 306.3 Train Acid POS C(C)O AZ89 >1000 -0.445 226.2 Train Acid NEG C[C@](Cc1ccc(c(c1)O)O)(C(=O)O)NN AZ9 c1cc(c(cc1Cn2c3ccc(c(c3cc2C(=O)O) 19.3 4.916 354.2 Test Acid POS F)O)Cl)Cl AZ90 c1cc(c(c(c1)Cl)C=NNC(=N)N)Cl 343.7 1.35 231.1 Test Base NEG AZ91 c1ccc(cc1)[C@H]2C[C@@H]2N 102.7 1.478 133.2 Train Base POS AZ92 c1cc(c(cc1CN2CCNCC2)C(=O)NCC34 124 4.997 402 Train Base POS CC5CC(C3)CC(C5)C4)Cl AZ93 c1cc(ccc1[C@H]([C@@H](CO)NC(=O >957.9 1.283 323.1 Test Neutral NEG )C(Cl)Cl)O)[N+](=O)[O-] AZ94 c1ccc2c(c1)C(=O)O[Bi](O2)O >1000 0.339 362.1 Train Neutral NEG AZ95 CC(C)C(=O)N[C@@H](CS)C(=O)O >1000 0.214 191.3 Train Acid NEG AZ96 C1CNC(=N)NC1C2C(=O)NCC(C(=O) >1000 -6.704 668.7 Train Base NEG NC(C(=O)NC(C(=O)N/C(=C\NC(=O)N) /C(=O)N2)CNC(=O)CC(CCCN)N)CO) N AZ97 CCCC(=O)c1cnc2c(c1Nc3ccc(cc3C)F) <10 5.861 428.5 Test Neutral POS cccc2OCCS(=O)C AZ98 CC1=C(N2[C@@H]([C@@H](C2=O) >1000 -2.507 363.4 Train Zwitterion NEG NC(=O)[C@H](c3ccc(cc3)O)N)SC1)C( =O)O AZ99 Cc1c(n2ccc3c(c2n1)OC(CC3)c4ccccc <10 3.12 294.4 Train Neutral POS 4)CO AZATHIOPRINE Cn1cnc(c1Sc2c3c(nc[nH]3)ncn2)[N+]( >1000 0.512 277.3 Train Neutral NEG =O)[O-] AZD0865 Cc1cccc(c1CNc2cc(cn3c2nc(c3C)C)C <10 3.195 366.5 Test Neutral POS (=O)NCCO)C AZD-4407 C[C@H]1C[C@](CCO1)(c2cc(sc2)Sc3 <10.93 2.13 375.5 Train Neutral POS ccc4c(c3)CC(=O)N4C)O AZD7009 CC(C)(C)C(=O)CN1CC2CN(CC(C1)O 513.6 3.573 384.5 Train Base NEG 2)CCCNc3ccc(cc3)C#N BECLOMETHASONE 23.67 2.125 408.9 Train Neutral POS C[C@H]1C[C@H]2[C@@H]3CCC4=C C(=O)C=C[C@@]4([C@]3([C@H](C[C @@]2([C@]1(C(=O)CO)O)C)O)Cl)C BENDROFLUMETHIAZIDE c1ccc(cc1)CC2Nc3cc(c(cc3S(=O)(=O) 69.55 1.727 421.4 Test Neutral POS N2)S(=O)(=O)N)C(F)(F)F BENOXAPROFEN CC(c1ccc2c(c1)nc(o2)c3ccc(cc3)Cl)C( 103.7 3.824 301.7 Test Acid POS =O)O BENOXINATE CCCCOc1cc(ccc1N)C(=O)OCCN(CC) 309.1 4.36 308.4 Test Base NEG CC BENSERAZIDE 116.6 -2.899 257.2 Train Base POS c1cc(c(c(c1CNNC(=O)C(CO)N)O)O)O BENZOCAINE CCOC(=O)c1ccc(cc1)N >1000 1.923 165.2 Train Neutral NEG BENZONATATE <10 2.54 603.7 Train Neutral POS CCCCNc1ccc(cc1)C(=O)OCCOCCOC COCCOCCOCCOCCOCCOCCOC BENZOYLPAS c1ccc(cc1)C(=O)Nc2ccc(c(c2)O)C(=O) >1000 2.784 257.2 Train Acid NEG O BENZTHIAZIDE c1ccc(cc1)CSCC2=Nc3cc(c(cc3S(=O) 57.43 2.172 431.9 Train Base POS (=O)N2)S(=O)(=O)N)Cl BENZYLPENICILLIN <10 1.747 334.4 Test Acid POS (PENICILLIN G) CC1([C@@H](N2[C@H](S1)[C@@H]( C2=O)NC(=O)Cc3ccccc3)C(=O)O)C BEPRIDIL CC(C)COCC(CN(Cc1ccccc1)c2ccccc2 <16.46 6.2 366.5 Train Base POS )N3CCCC3 BETA CAROTENE CC1=C(C(CCC1)(C)C)/C=C/C(=C/C= <10 15.23 536.9 Test Neutral POS C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2 =C(CCCC2(C)C)C)\C)\C)/C)/C BETAINE C[N+](C)(C)CC(=O)O >1000 -4.173 118.2 Train Zwitterion NEG BETAXOLOL CC(C)NCC(COc1ccc(cc1)CCOCC2CC >1000 2.319 307.4 Test Base NEG 2)O BETHANECHOL CC(C[N+](C)(C)C)OC(=O)N >1000 -4.01 161.2 Train Cationic NEG BEZAFIBRATE CC(C)(C(=O)O)Oc1ccc(cc1)CCNC(=O 180.8 3.698 361.8 Train Acid POS )c2ccc(cc2)Cl BISACODYL CC(=O)Oc1ccc(cc1)C(c2ccc(cc2)OC( 56.36 2.848 361.4 Train Neutral POS =O)C)c3ccccn3 BISMUTH SUBSALICYLATE c1ccc(c(c1)C(=O)O)O >1000 2.187 138.1 Train Acid NEG BOSENTAN <25.3 4.167 551.6 Train Acid POS CC(C)(C)c1ccc(cc1)S(=O)(=O)Nc2c(c( nc(n2)c3ncccn3)OCCO)Oc4ccccc4OC BRETYLIUM CC[N+](C)(C)Cc1ccccc1Br >1000 -1.246 243.2 Train Cationic NEG BROMHEXINE 20.27 4.884 376.1 Train Base POS CN(Cc1cc(cc(c1N)Br)Br)C2CCCCC2 BUMETANIDE CCCCNc1cc(cc(c1Oc2ccccc2)S(=O)(= 526.4 3.372 364.4 Test Acid NEG O)N)C(=O)O BUPHENINE CC(CCc1ccccc1)NC(C)C(c2ccc(cc2)O 280.3 3.006 299.4 Test Base POS )O BUPROPION >1000 3.211 239.7 Train Base NEG CC(C(=O)c1cccc(c1)Cl)NC(C)(C)C BUSPIRONE c1cnc(nc1)N2CCN(CC2)CCCCN3C(= 59.63 2.185 385.5 Train Base POS O)CC4(CCCC4)CC3=O BUSULFAN CS(=O)(=O)OCCCCOS(=O)(=O)C >1000 -0.592 246.3 Train Neutral NEG BUTACAINE CCCCN(CCCC)CCCOC(=O)c1ccc(cc1 487.5 5.007 306.4 Test Base NEG )N CAFFEINE Cn1cnc2c1c(=O)n(c(=O)n2C)C >1000 -0.04 194.2 Train Neutral NEG Cangrelor CSCCNc1c2c(nc(n1)SCCC(F)(F)F)n(c >1000 3.024 776.4 Train Acid NEG n2)[C@H]3[C@@H]([C@@H]([C@H]( O3)COP(=O)(O)OP(=O)(C(P(=O)(O)O )(Cl)Cl)O)O)O CAPOBENIC ACID COc1cc(cc(c1OC)OC)C(=O)NCCCCC >1000 1.045 325.4 Test Acid NEG C(=O)O CAPSAICIN CC(C)/C=C/CCCCC(=O)NCc1ccc(c(c1 <10 3.75 305.4 Train Neutral POS )OC)O CARBACHOL C[N+](C)(C)CCOC(=O)N >1000 -4.319 147.2 Train Cationic NEG CARBAMAZEPINE >1000 2.38 236.3 Test Neutral NEG c1ccc2c(c1)C=Cc3ccccc3N2C(=O)N CARBIMAZOLE CCOC(=O)n1ccn(c1=S)C >1000 1.679 186.2 Train Neutral NEG CARBINOXAMINE >1000 2.668 290.8 Train Base NEG CN(C)CCOC(c1ccc(cc1)Cl)c2ccccn2 CARTEOLOL CC(C)(C)NCC(COc1cccc2c1CCC(=O) >1000 1.289 292.4 Test Base NEG N2)O CHLORIMIPRAMINE CN(C)CCCN1c2ccccc2CCc3c1cc(cc3) 37.4 5.921 314.9 Train Base POS Cl CHLOROPROCAINE CCN(CC)CCOC(=O)c1ccc(cc1Cl)N >1000 2.909 270.8 Train Base NEG CHLORPROMAZINE CN(C)CCCN1c2ccccc2Sc3c1cc(cc3)C 90.97 5.3 318.9 Test Base POS l CHLORPROPAMIDE >1000 2.35 276.7 Test Acid NEG CCCNC(=O)NS(=O)(=O)c1ccc(cc1)Cl CHLORPROTHIXENE CN(C)CC/C=C/1\c2ccccc2Sc3c1cc(cc 27.47 5.482 315.9 Train Base POS 3)Cl CINCHOCAINE CCCCOc1cc(c2ccccc2n1)C(=O)NCCN 41.65 5.354 343.5 Train Base POS (CC)CC CINCHOPHEN >813.5 4.281 249.3 Train Acid NEG c1ccc(cc1)c2cc(c3ccccc3n2)C(=O)O CIPROFLOXACIN c1c2c(cc(c1F)N3CCNCC3)n(cc(c2=O) >1000 -0.725 331.3 Train Zwitterion NEG C(=O)O)C4CC4 CLAVULANATE POTASSIUM C1[C@@H]2N(C1=O)[C@H](/C(=C/C >1000 -1.065 199.2 Test Acid NEG O)/O2)C(=O)O CLOMIPHENE CCN(CC)CCOc1ccc(cc1)/C(=C(\c2ccc <10 7.151 406 Train Base POS cc2)/Cl)/c3ccccc3 CLOTRIMAZOLE c1ccc(cc1)C(c2ccccc2)(c3ccccc3Cl)n4 <10 5.004 344.8 Test Base POS ccnc4 CLOXACILLIN Cc1c(c(no1)c2ccccc2Cl)C(=O)N[C@H 41.57 2.516 435.9 Train Acid POS ]3[C@@H]4N(C3=O)[C@H](C(S4)(C) C)C(=O)O CLOXYQUIN c1cc2c(ccc(c2nc1)O)Cl 356.7 2.913 179.6 Train Acid NEG CLOZAPINE CN1CCN(CC1)C2=Nc3cc(ccc3Nc4c2c 75.14 3.714 326.8 Train Base POS ccc4)Cl CO-DIOVAN 31.07 4.859 435.5 Test Acid POS CCCCC(=O)N(Cc1ccc(cc1)c2ccccc2c 3[nH]nnn3)[C@@H](C(C)C)C(=O)O COLCHICINE CC(=O)N[C@H]1CCc2cc(c(c(c2- 298.7 1.195 399.4 Train Neutral POS c3c1cc(=O)c(cc3)OC)OC)OC)OC CORTISONE C[C@]12CCC(=O)C=C1CC[C@@H]3[ 108.1 1.485 360.4 Test Neutral POS C@@H]2C(=O)C[C@]4([C@H]3CC[C @@]4(C(=O)CO)O)C COUMARIN c1ccc2c(c1)ccc(=O)o2 >1000 1.412 146.1 Train Neutral NEG CROMOLYN >1000 1.481 468.4 Train Acid NEG c1cc2c(c(c1)OCC(COc3cccc4c3c(=O) cc(o4)C(=O)O)O)c(=O)cc(o2)C(=O)O CYCLANDELATE CC1CC(CC(C1)(C)C)OC(=O)C(c2cccc 15.03 4.643 276.4 Train Neutral POS c2)O CYCLOBENZAPRINE CN(C)CCC=C1c2ccccc2C=Cc3c1cccc 107.4 5.097 275.4 Train Base POS 3 CYCLOSERINE C1[C@H](C(=O)NO1)N >1000 -1.192 102.1 Train Base NEG CYCLOSPORIN A CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C <10 14.36 1203 Train Neutral POS (=O)N(C(C(=O)NC(C(=O)NC(C(=O)N( C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(= O)N1)C(C(C)C/C=C/C)O)C)C(C)C)C)C C(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C( C)C)CC(C)C)C)C CYSTEAMINE C(CS)N 331 -0.252 77.15 Test Base NEG DAPSONE >1000 0.886 248.3 Test Neutral NEG c1cc(ccc1N)S(=O)(=O)c2ccc(cc2)N DASATINIB Cc1cccc(c1NC(=O)c2cnc(s2)Nc3cc(nc <10 2.529 488 Train Base POS (n3)C)N4CCN(CC4)CCO)Cl DAZOXIBEN c1cc(ccc1C(=O)O)OCCn2ccnc2 >1000 1.716 232.2 Train Acid NEG DEBRISOQUIN c1ccc2c(c1)CCN(C2)C(=N)N >951.8 0.895 175.2 Test Base NEG DERACOXIB COc1ccc(cc1F)c2cc(nn2c3ccc(cc3)S( 20.18 3.122 397.4 Train Neutral POS =O)(=O)N)C(F)F DESIPRAMINE CNCCCN1c2ccccc2CCc3c1cccc3 150.4 4.468 266.4 Train Base POS DEVAZEPIDE CN1c2ccccc2C(=NC(C1=O)NC(=O)c3 <10 3.694 408.5 Train Neutral POS cc4ccccc4[nH]3)c5ccccc5 DEXTROTHYROXINE c1c(cc(c(c1I)Oc2cc(c(c(c2)I)O)I)I)C[C <10 3.508 776.9 Train Zwitterion POS SODIUM @@H](C(=O)O)N DIAZOXIDE CC1=Nc2ccc(cc2S(=O)(=O)N1)Cl >1000 1.201 230.7 Train Base NEG DIBENZOTHIOPHENE c1ccc2c(c1)c3ccccc3s2 387.9 4.556 184.3 Train Neutral NEG DICHLORPHENAMIDE c1c(cc(c(c1S(=O)(=O)N)Cl)Cl)S(=O)(= >919.1 0.241 305.2 Train Neutral NEG O)N DICLOFENAC 64.97 4.726 296.2 Test Acid POS c1ccc(c(c1)CC(=O)O)Nc2c(cccc2Cl)Cl DICUMAROL c1ccc2c(c1)c(c(c(=O)o2)Cc3c(c4ccccc 39.93 3.658 336.3 Test Neutral POS 4oc3=O)O)O DICYCLOMINE CCN(CC)CCOC(=O)C1(CCCCC1)C2C 40.04 6.138 309.5 Train Base POS CCCC2 DIFTALONE c1ccc2c(c1)CN3C(=O)c4ccccc4CN3C >1000 2.408 264.3 Train Neutral NEG 2=O DIGITOXIN CC1C(C(CC(O1)OC2C(OC(CC2O)OC <10 2.854 764.9 Train Neutral POS 3C(OC(CC3O)OC4CCC5(C(C4)CCC6 C5CCC7(C6(CCC7C8=CC(=O)OC8)O )C)C)C)C)O)O DIGOXIN 264.1 1.423 780.9 Train Neutral POS C[C@@H]1[C@H]([C@H](C[C@@H]( O1)O[C@@H]2[C@H](O[C@H](C[C@ @H]2O)O[C@@H]3[C@H](O[C@H](C [C@@H]3O)O[C@H]4CC[C@]5([C@ @H](C4)CC[C@@H]6[C@@H]5C[C @H]([C@]7([C@@]6(CC[C@@H]7C8 =CC(=O)OC8)O)C)O)C)C)C)O)O DIHYDRALAZINE c1ccc2c(c1)c(nnc2NN)NN >1000 1.754 190.2 Train Neutral NEG DIIODOHYDROXYQUINOLIN >1000 4.139 397 Test Acid NEG E c1cc2c(cc(c(c2nc1)O)I)I DIMENHYDRINATE CN(C)CCOC(c1ccccc1)c2ccccc2 >1000 3.452 255.4 Test Base NEG DIMETHADIONE CC1(C(=O)NC(=O)O1)C >1000 0.507 129.1 Train Neutral NEG DIMETHISOQUIN 68.68 4.824 272.4 Train Base POS CCCCc1cc2ccccc2c(n1)OCCN(C)C DIPHENYLPYRALINE 508.8 3.206 281.4 Train Base NEG CN1CCC(CC1)OC(c2ccccc2)c3ccccc3 DIPROPHYLLINE Cn1c2c(c(=O)n(c1=O)C)n(cn2)CC(CO >1000 -1.286 254.2 Test Neutral NEG (DYPHYLLINE) )O DISULFIRAM CCN(CC)C(=S)SSC(=S)N(CC)CC <10 3.88 296.5 Train Neutral POS DITIOCARB CCN(CC)C(=S)S 69.26 0.59 149.3 Train Neutral POS DOBUTAMINE CC(CCc1ccc(cc1)O)NCCc2ccc(c(c2)O >1000 2.433 301.4 Train Base NEG )O DOCOSANOL CCCCCCCCCCCCCCCCCCCCCCO >1000 10.35 326.6 Test Neutral NEG DOFETILIDE CN(CCc1ccc(cc1)NS(=O)(=O)C)CCOc 708.4 1.994 441.6 Train Base NEG 2ccc(cc2)NS(=O)(=O)C DONEPEZIL COc1cc2c(cc1OC)C(=O)C(C2)CC3CC 145.6 4.598 379.5 Test Base POS N(CC3)Cc4ccccc4 DOPAMINE c1cc(c(cc1CCN)O)O >1000 0.169 153.2 Train Base NEG DOPEXAMINE c1ccc(cc1)CCNCCCCCCNCCc2ccc(c( >1000 3.316 356.5 Train Base NEG c2)O)O DOXYLAMINE >1000 2.354 270.4 Train Base NEG CC(c1ccccc1)(c2ccccn2)OCCN(C)C DROPERIDOL c1ccc2c(c1)[nH]c(=O)n2C3=CCN(CC3 <10 3.056 379.4 Train Base POS )CCCC(=O)c4ccc(cc4)F DYCLONINE CCCCOc1ccc(cc1)C(=O)CCN2CCCC 275.4 4.832 289.4 Train Base POS C2 EBSELEN <10 3.704 274.2 Test Neutral POS c1ccc(cc1)n2c(=O)c3ccccc3[se]2 ECONAZOLE c1cc(ccc1COC(Cn2ccnc2)c3ccc(cc3Cl <10 5.099 381.7 Train Base POS )Cl)Cl ENALAPRILAT >1000 0.748 348.4 Train Zwitterion NEG C[C@@H](C(=O)N1CCC[C@H]1C(=O )O)N[C@@H](CCc2ccccc2)C(=O)O ENPROFYLLINE >1000 0.396 194.2 Train Neutral NEG CCCn1c2c(c(=O)[nH]c1=O)[nH]cn2 ENROFLOXACIN CCN1CCN(CC1)c2cc3c(cc2F)c(=O)c( >1000 0.379 359.4 Train Zwitterion NEG cn3C4CC4)C(=O)O EPANOLOL c1ccc(c(c1)C#N)OCC(CNCCNC(=O)C 244.4 1.04 369.4 Train Base POS c2ccc(cc2)O)O ESTRIOL C[C@]12CC[C@@H]3c4ccc(cc4CC[C >1000 3.2 288.4 Train Neutral NEG @H]3[C@@H]1C[C@H]([C@@H]2O) O)O ESTRONE C[C@]12CC[C@@H]3c4ccc(cc4CC[C >1000 3.382 270.4 Test Neutral NEG @H]3[C@@H]1CCC2=O)O ETHACRIDINE 43.48 3.372 253.3 Train Neutral POS CCOc1ccc2c(c1)c(c3ccc(cc3n2)N)N ETHIONAMIDE CCc1cc(ccn1)C(=S)N >1000 1.729 166.2 Train Neutral NEG ETHOPROPAZINE CCN(CC)C(C)CN1c2ccccc2Sc3c1ccc 139.2 5.458 312.5 Test Base POS c3 ETHOSUXIMIDE CCC1(CC(=O)NC1=O)C >1000 0.395 141.2 Train Neutral NEG ETHOTOIN CCN1C(=O)C(NC1=O)c2ccccc2 >791.9 1.482 204.2 Train Neutral NEG ETHYL CARBAMATE CCOC(=O)N >1000 -0.175 89.09 Train Neutral NEG ETIDRONATE CC(O)(P(=O)(O)O)P(=O)(O)O >1000 -2.543 206 Train Acid NEG ETOMIDATE CCOC(=O)c1cncn1C(C)c2ccccc2 61.61 2.417 244.3 Train Neutral POS FELBAMATE >1000 0.497 238.2 Train Neutral NEG c1ccc(cc1)C(COC(=O)N)COC(=O)N FENCLOFENAC 235.7 4.708 297.1 Train Acid POS c1ccc(c(c1)CC(=O)O)Oc2ccc(cc2Cl)Cl FENCLOZIC ACID c1cc(ccc1c2nc(cs2)CC(=O)O)Cl >1000 2.576 253.7 Train Acid NEG FENOBAM CN1CC(=O)N=C1NC(=O)Nc2cccc(c2) >1000 2.195 266.7 Test Base NEG Cl FENOLDOPAM c1cc(ccc1C2CNCCc3c2cc(c(c3Cl)O)O >1000 2.4 305.8 Train Zwitterion NEG )O FENOTEROL CC(Cc1ccc(cc1)O)NCC(c2cc(cc(c2)O) >1000 0.984 303.4 Train Base NEG O)O FLECAINIDE c1cc(c(cc1OCC(F)(F)F)C(=O)NCC2C 217.6 3.66 414.3 Train Base POS CCCN2)OCC(F)(F)F FLUCLOXACILLIN Cc1c(c(no1)c2c(cccc2Cl)F)C(=O)N[C <10 2.661 453.9 Train Acid POS @H]3[C@@H]4N(C3=O)[C@H](C(S4) (C)C)C(=O)O FLUDROXYCORTIDE C[C@]12CCC(=O)C=C1[C@H](C[C@ 71.19 2.873 436.5 Train Neutral POS @H]3[C@@H]2[C@H](C[C@]4([C@H ]3C[C@@H]5[C@]4(OC(O5)(C)C)C(= O)CO)C)O)F FLUMAZENIL CCOC(=O)c1c2n(cn1)- >733.5 1.291 303.3 Train Neutral NEG c3ccc(cc3C(=O)N(C2)C)F FLUMETASONE C[C@@H]1C[C@H]2[C@@H]3C[C@ 68.46 1.828 410.5 Train Neutral POS @H](C4=CC(=O)C=C[C@@]4([C@]3( [C@H](C[C@@]2([C@]1(C(=O)CO)O) C)O)F)C)F FLUNARIZINE c1ccc(cc1)/C=C/CN2CCN(CC2)C(c3c <10 6.337 404.5 Train Base POS cc(cc3)F)c4ccc(cc4)F FLUOROMETHOLONE C[C@H]1C[C@H]2[C@@H]3CC[C@ 100.9 2.111 376.5 Train Neutral POS @]([C@]3(C[C@@H]([C@@]2([C@@ ]4(C1=CC(=O)C=C4)C)F)O)C)(C(=O) C)O FLUOXETINE CNCCC(c1ccccc1)Oc2ccc(cc2)C(F)(F) 143.8 4.566 309.3 Train Base POS F FLUPHENAZINE c1ccc2c(c1)N(c3cc(ccc3S2)C(F)(F)F) 25.82 4.118 437.5 Train Base POS CCCN4CCN(CC4)CCO FLURBIPROFEN 724.7 3.754 244.3 Train Acid NEG CC(c1ccc(c(c1)F)c2ccccc2)C(=O)O FLUTAMIDE CC(C)C(=O)Nc1ccc(c(c1)C(F)(F)F)[N+ 60.78 3.335 276.2 Train Neutral POS ](=O)[O-] FOLIC ACID c1cc(ccc1C(=O)N[C@@H](CCC(=O)O >1000 -2.376 441.4 Train Acid NEG )C(=O)O)NCc2cnc3c(n2)c(=O)nc([nH] 3)N Folinic acid c1cc(ccc1C(=O)N[C@@H](CCC(=O)O >1000 -1.452 473.4 Train Acid NEG )C(=O)O)NCC2CNc3c(c(=O)[nH]c(n3) N)N2C=O FPL-55712 <10 5.191 498.5 Train Acid POS CCCc1c(ccc(c1O)C(=O)C)OCC(COc2 ccc3c(=O)cc(oc3c2CCC)C(=O)O)O FUROSEMIDE c1cc(oc1)CNc2cc(c(cc2C(=O)O)S(=O) >964.8 1.9 330.7 Train Acid NEG (=O)N)Cl GABAPENTIN C1CCC(CC1)(CC(=O)O)CN >1000 -0.66 171.2 Train Zwitterion NEG Gavestinel c1ccc(cc1)NC(=O)/C=C/c2c3c(cc(cc3 <10 5.188 375.2 Test Acid POS Cl)Cl)[nH]c2C(=O)O GEMIFLOXACIN CO/N=C/1\CN(CC1CN)c2c(cc3c(=O)c( >1000 -1.245 389.4 Train Zwitterion NEG cn(c3n2)C4CC4)C(=O)O)F GLAFENINE c1ccc(c(c1)C(=O)OCC(CO)O)Nc2ccnc <14.93 4.189 372.8 Train Neutral POS 3c2ccc(c3)Cl GLIBENCLAMIDE <10 4.239 494 Train Acid POS COc1ccc(cc1C(=O)NCCc2ccc(cc2)S(= O)(=O)NC(=O)NC3CCCCC3)Cl GLICLAZIDE Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2CC 590.8 1.093 323.4 Train Acid NEG 3CCCC3C2 GLIMEPIRIDE CCC1=C(CN(C1=O)C(=O)NCCc2ccc( <10 3.962 490.6 Train Acid POS cc2)S(=O)(=O)NC(=O)N[C@H]3CC[C @@H](CC3)C)C GLYCERYL GUAIACOLATE >1000 0.102 198.2 Test Neutral NEG COc1ccccc1OCC(CO)O GUAIACOL COc1ccccc1O >1000 1.324 124.1 Train Neutral NEG GUANETHIDINE C1CCCN(CCC1)CCNC(=N)N >1000 1.339 198.3 Train Base NEG GW 572016 CS(=O)(=O)CCNCc1ccc(o1)c2ccc3c(c <10 5.965 581.1 Train Base POS 2)c(ncn3)Nc4ccc(c(c4)Cl)OCc5cccc(c 5)F HALCINONIDE C[C@]12CCC(=O)C=C1CC[C@@H]3[ <10 3.311 455 Train Neutral POS C@@]2([C@H](C[C@]4([C@H]3C[C @@H]5[C@]4(OC(O5)(C)C)C(=O)CCl )C)O)F HALOPERIDOL c1cc(ccc1C(=O)CCCN2CCC(CC2)(c3 22.76 3.849 375.9 Train Base POS ccc(cc3)Cl)O)F HEXAMETHYLENE >1000 -0.734 200.3 Test Neutral NEG BISACETAMIDE CC(=O)NCCCCCCNC(=O)C HEXOPRENALINE c1cc(c(cc1C(CNCCCCCCNCC(c2ccc( >1000 0.053 420.5 Train Base NEG c(c2)O)O)O)O)O)O HEXYLCAINE 505.7 3.944 261.4 Train Base NEG HYDROCHLORIDE CC(CNC1CCCCC1)OC(=O)c2ccccc2 HISTAMINE c1c(nc[nH]1)CCN >1000 -0.968 111.1 Train Base NEG HYCANTHONE CCN(CC)CCNc1ccc(c2c1c(=O)c3cccc 29.8 3.657 356.5 Train Base POS c3s2)CO HYDRALAZINE c1ccc2c(c1)cnnc2NN >1000 1.173 160.2 Train Neutral NEG HYDROFLUMETHIAZIDE c1c(c(cc2c1NCNS2(=O)=O)S(=O)(=O) >1000 -0.21 331.3 Train Neutral NEG N)C(F)(F)F HYDROXYZINE c1ccc(cc1)C(c2ccc(cc2)Cl)N3CCN(CC 72.91 3.995 374.9 Train Base POS 3)CCOCCO IBUPROFEN CC(C)Cc1ccc(cc1)C(C)C(=O)O >789 3.679 206.3 Train Acid NEG IMATINIB <10 4.529 493.6 Train Base POS Cc1ccc(cc1Nc2nccc(n2)c3cccnc3)NC( =O)c4ccc(cc4)CN5CCN(CC5)C IMILOXAN CCn1ccnc1CC2COc3ccccc3O2 61.65 2.297 244.3 Train Base POS INDALPINE >1000 3.391 228.3 Train Base NEG c1ccc2c(c1)c(c[nH]2)CCC3CCNCC3 INDAPAMIDE CC1Cc2ccccc2N1NC(=O)c3ccc(c(c3) 144.7 2.957 365.8 Test Neutral POS S(=O)(=O)N)Cl INDOMETHACIN Cc1c(c2cc(ccc2n1C(=O)c3ccc(cc3)Cl) 49.32 4.18 357.8 Train Acid POS OC)CC(=O)O INDORAMIN c1ccc(cc1)C(=O)NC2CCN(CC2)CCc3 109 2.836 347.5 Test Base POS c[nH]c4c3cccc4 IODIPAMIDE MEGLUMINE >969.9 4.191 1140 Train Acid NEG c1c(c(c(c(c1I)NC(=O)CCCCC(=O)Nc2 c(cc(c(c2I)C(=O)O)I)I)I)C(=O)O)I IPRONIAZID CC(C)NNC(=O)c1ccncc1 >952.6 0.256 179.2 Train Neutral NEG IPSAPIRONE c1ccc2c(c1)C(=O)N(S2(=O)=O)CCCC 31.17 1.354 401.5 Train Base POS N3CCN(CC3)c4ncccn4 ISOETHARINE >1000 0.991 239.3 Test Base NEG CCC(C(c1ccc(c(c1)O)O)O)NC(C)C ISONIAZID c1cnccc1C(=O)NN >1000 -0.668 137.1 Train Neutral NEG ISOPROTERENOL CC(C)NCC(c1ccc(c(c1)O)O)O >986.2 0.153 211.3 Train Base NEG ISOXSUPRINE CC(COc1ccccc1)NC(C)C(c2ccc(cc2)O 572.5 2.615 301.4 Test Base NEG )O

IVERMECTIN CC[C@H](C)[C@@H]1[C@H](CC[C@ <10 5.388 875.1 Train Neutral POS @]2(O1)C[C@@H]3C[C@H](O2)C/C= C(/[C@H]([C@H](/C=C/C=C/4\CO[C@ H]5[C@@]4([C@@H](C=C([C@H]5O) C)C(=O)O3)O)C)O[C@H]6C[C@@H]( [C@H]([C@@H](O6)C)O[C@H]7C[C @@H]([C@H]([C@@H](O7)C)O)OC) OC)\C)C KETOCONAZOLE CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C 4.1 3.635 531.4 Train Base POS @H]3CO[C@](O3)(Cn4ccnc4)c5ccc(c c5Cl)Cl KETOTIFEN CN1CCC(=C2c3ccccc3CC(=O)c4c2cc >428.6 3.593 309.4 Train Base NEG s4)CC1 KS-01019 <10 4.481 418.6 Test Neutral POS CCC(C)(C)C(=O)O[C@H]1C[C@H](C =C2[C@H]1[C@H]([C@H](C=C2)C)C C[C@@H]3C[C@H](CC(=O)O3)O)C LABETALOL CC(CCc1ccccc1)NCC(c2ccc(c(c2)C(= 649.1 2.5 328.4 Train Base NEG O)N)O)O LECOZOTAN C[C@H](CN(c1ccccn1)C(=O)c2ccc(cc <10 3.193 483.6 Test Base POS 2)C#N)N3CCN(CC3)c4cccc5c4OCCO 5 LEFLUNOMIDE 110.4 2.324 270.2 Test Neutral POS Cc1c(cno1)C(=O)Nc2ccc(cc2)C(F)(F)F LEMAKALIM CC1([C@H]([C@@H](c2cc(ccc2O1)C 353.3 1.106 286.3 Train Neutral NEG #N)N3CCCC3=O)O)C LETROZOLE c1cc(ccc1C#N)C(c2ccc(cc2)C#N)n3cn 225.2 1.429 285.3 Test Neutral POS cn3 LEVAMISOLE c1ccc(cc1)[C@H]2CN3CCSC3=N2 >1000 1.844 204.3 Train Base NEG LEVETIRACETAM CC[C@@H](C(=O)N)N1CCCC1=O >1000 -0.344 170.2 Test Neutral NEG LEVOFLOXACIN C[C@H]1COc2c3n1cc(c(=O)c3cc(c2N >1000 -0.508 361.4 Train Zwitterion NEG 4CCN(CC4)C)F)C(=O)O LIGUSTRAZINE Cc1c(nc(c(n1)C)C)C >1000 1.584 136.2 Test Neutral NEG LIOTHYRONINE SODIUM c1cc(c(cc1Oc2c(cc(cc2I)C[C@@H](C( <11.27 2.631 651 Test Zwitterion POS =O)O)N)I)I)O LIPOIC ACID C1CSSC1CCCCC(=O)O >1000 2.386 206.3 Test Acid NEG LONAPALENE CC(=O)Oc1c2ccc(cc2c(c(c1OC)OC)O 14.39 1.758 338.7 Test Neutral POS C(=O)C)Cl LOSARTAN CCCCc1nc(c(n1Cc2ccc(cc2)c3ccccc3 <10 3.852 422.9 Train Acid POS c4[nH]nnn4)CO)Cl LY 171883 CCCc1c(ccc(c1O)C(=O)C)OCCCCc2[ <10.74 3.664 318.4 Train Acid POS nH]nnn2 MECLOFENAMIC ACID 27.24 6.406 296.2 Train Acid POS Cc1ccc(c(c1Cl)Nc2ccccc2C(=O)O)Cl MEGESTROL ACETATE CC1=C[C@@H]2[C@H](CC[C@]3([C <10 3.772 384.5 Test Neutral POS @H]2CC[C@@]3(C(=O)C)OC(=O)C)C )[C@@]4(C1=CC(=O)CC4)C MELPHALAN 93.75 -0.207 305.2 Train Zwitterion POS c1cc(ccc1CC(C(=O)O)N)N(CCCl)CCCl MEMANTINE CC12CC3CC(C1)(CC(C3)(C2)N)C >1000 3.033 179.3 Train Base NEG MEPENZOLATE BROMIDE C[N+]1(CCCC(C1)OC(=O)C(c2ccccc2 >1000 0.157 340.4 Test Cationic NEG )(c3ccccc3)O)C MEPHENESIN Cc1ccccc1OCC(CO)O >1000 0.862 182.2 Train Neutral NEG MEPHENYTOIN >1000 2.001 218.3 Test Neutral NEG CCC1(C(=O)N(C(=O)N1)C)c2ccccc2 MEPINDOLOL Cc1cc2c([nH]1)cccc2OCC(CNC(C)C) 35.87 2.17 262.4 Train Base POS O MEPRYLCAINE CCCNC(C)(C)COC(=O)c1ccccc1 >1000 3.37 235.3 Train Base NEG MEPYRAMINE >1000 3.225 285.4 Test Base NEG CN(C)CCN(Cc1ccc(cc1)OC)c2ccccn2 MESALAZINE c1cc(c(cc1N)C(=O)O)O 381.4 1.056 153.1 Test Acid NEG METADOXINE Cc1c(c(c(cn1)CO)CO)O >1000 -0.345 169.2 Train Neutral NEG METAPROTERENOL CC(C)NCC(c1cc(cc(c1)O)O)O >1000 0.083 211.3 Train Base NEG METARAMINOL >1000 -0.083 167.2 Train Base NEG C[C@@H]([C@@H](c1cccc(c1)O)O)N METERGOLINE Cn1cc2c3c1cccc3[C@H]4C[C@H](CN <10 4.694 403.5 Train Base POS ([C@@H]4C2)C)CNC(=O)OCc5ccccc 5 METHAPYRILENE CN(C)CCN(Cc1cccs1)c2ccccn2 >1000 2.952 261.4 Train Base NEG METHIMAZOLE Cn1cc[nH]c1=S >1000 -0.34 114.2 Train Neutral NEG METHOCARBAMOL COc1ccccc1OCC(COC(=O)N)O >1000 0.146 241.2 Train Neutral NEG METHOXAMINE CC(C(c1cc(ccc1OC)OC)O)N >1000 0.592 211.3 Train Base NEG METHYLTHIOURACIL Cc1cc(=O)[nH]c(=S)[nH]1 >1000 -0.087 142.2 Train Neutral NEG METRIZAMIDE >1000 -1.699 789.1 Test Neutral NEG CC(=O)Nc1c(c(c(c(c1I)N(C)C(=O)C)I) C(=O)NC2C(C(C(OC2O)CO)O)O)I METYRAPONE CC(C)(c1cccnc1)C(=O)c2cccnc2 229.3 1.459 226.3 Test Neutral POS MIANSERIN 46.82 3.762 264.4 Test Base POS CN1CCN2c3ccccc3Cc4ccccc4C2C1 MINIZIDE COc1cc2c(cc1OC)nc(nc2N)N3CCN(C 171.8 2.028 383.4 Train Neutral POS C3)C(=O)c4ccco4 MINOCROMIL CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >1000 3.662 356.3 Train Acid NEG cc(n2)C(=O)O)NC MITOTANE <10 6.06 320 Test Neutral POS c1ccc(c(c1)C(c2ccc(cc2)Cl)C(Cl)Cl)Cl MOXIFLOXACIN COc1c2c(cc(c1N3C[C@@H]4CCCN[ >1000 -0.082 401.4 Train Zwitterion NEG C@@H]4C3)F)c(=O)c(cn2C5CC5)C(= O)O N-ACETYL PROCAINAMIDE CCN(CC)CCNC(=O)c1ccc(cc1)NC(=O >1000 1.643 277.4 Test Base NEG )C NAFRONYL CCN(CC)CCOC(=O)C(Cc1cccc2c1ccc <11.04 5.439 383.5 Train Base POS c2)CC3CCCO3 NAFTOPIDIL COc1ccccc1N2CCN(CC2)CC(COc3cc <10 4.433 392.5 Test Base POS cc4c3cccc4)O NAPHAZOLINE c1ccc2c(c1)cccc2CC3=NCCN3 >1000 3.826 210.3 Train Base NEG NAPROXEN C[C@@H](c1ccc2cc(ccc2c1)OC)C(=O >1000 2.816 230.3 Train Acid NEG )O NEDOCROMIL CCCc1c2c(cc3c1oc(cc3=O)C(=O)O)c( >1000 1.495 371.3 Train Acid NEG =O)cc(n2CC)C(=O)O NEFAZODONE CCc1nn(c(=O)n1CCOc2ccccc2)CCCN <10 5.725 470 Train Base POS 3CCN(CC3)c4cccc(c4)Cl NEOSTIGMINE >1000 -2.812 223.3 Test Cationic NEG CN(C)C(=O)Oc1cccc(c1)[N+](C)(C)C NEVIRAPINE Cc1ccnc2c1NC(=O)c3cccnc3N2C4CC 294.6 2.65 266.3 Train Neutral POS 4 NICARDIPINE CC1=C(C(C(=C(N1)C)C(=O)OCCN(C) <10 5.23 479.5 Train Base POS Cc2ccccc2)c3cccc(c3)[N+](=O)[O- ])C(=O)OC NIFEDIPINE CC1=C(C(C(=C(N1)C)C(=O)OC)c2ccc 18.65 3.125 346.3 Test Neutral POS cc2[N+](=O)[O-])C(=O)OC NILVADIPINE <10 3.038 385.4 Train Neutral POS CC1=C(C(C(=C(N1)C#N)C(=O)OC)c2 cccc(c2)[N+](=O)[O-])C(=O)OC(C)C NOMIFENSIN CN1Cc2c(cccc2N)C(C1)c3ccccc3 >1000 2.372 238.3 Train Base NEG OFLOXACIN CC1COc2c3n1cc(c(=O)c3cc(c2N4CC >1000 -0.508 361.4 Train Zwitterion NEG N(CC4)C)F)C(=O)O OLANZAPINE Cc1cc2c(s1)Nc3ccccc3N=C2N4CCN( 54.57 3.009 312.4 Train Base POS CC4)C ORPHENADRINE >1000 3.901 269.4 Train Base NEG Cc1ccccc1C(c2ccccc2)OCCN(C)C OXEDRINE CNCC(c1ccc(cc1)O)O >1000 -0.088 167.2 Train Base NEG OXETHAZAINE <10 4.721 467.7 Test Base POS CC(C)(Cc1ccccc1)N(C)C(=O)CN(CCO )CC(=O)N(C)C(C)(C)Cc2ccccc2 OXIBENDAZOLE CCCOc1ccc2c(c1)nc([nH]2)NC(=O)O >1000 3.073 249.3 Train Neutral NEG C OXPRENOLOL CC(C)NCC(COc1ccccc1OCC=C)O >1000 2.092 265.4 Test Base NEG PANTOLACTONE CC1(COC(=O)C1O)C >1000 -0.361 130.1 Train Neutral NEG PANTOTHENIC ACID CC(C)(CO)[C@H](C(=O)NCCC(=O)O) >1000 -1.494 219.2 Test Acid NEG O PAPAVERINE COc1ccc(cc1OC)Cc2c3cc(c(cc3ccn2) <10 3.782 339.4 Train Neutral POS OC)OC PARBENDAZOLE CCCCc1ccc2c(c1)nc([nH]2)NC(=O)O >1000 3.795 247.3 Test Neutral NEG C PARGYLINE CN(CC#C)Cc1ccccc1 >1000 2.576 159.2 Test Base NEG PAROXETINE c1cc(ccc1[C@@H]2CCNC[C@H]2CO 68.91 4.238 329.4 Test Base POS HYDROCHLORIDE c3ccc4c(c3)OCO4)F PENTAMIDINE c1cc(ccc1C(=N)N)OCCCCCOc2ccc(cc >1000 2.308 340.4 Train Base NEG 2)C(=N)N PENTYLENETETRAZOLE C1CCc2nnnn2CC1 >1000 1.195 138.2 Train Neutral NEG PERHEXILINE C1CCC(CC1)C(CC2CCCCN2)C3CCC 14.36 7.153 277.5 Train Base POS CC3 PERPHENAZINE c1ccc2c(c1)N(c3cc(ccc3S2)Cl)CCCN4 34.84 3.807 404 Train Base POS CCN(CC4)CCO PF-1913539 Cc1ccc2c(c1)c3c(n2CCc4ccc(nc4)C)C 135.9 4.095 319.5 Train Base POS CN(C3)C PHENACEMIDE c1ccc(cc1)CC(=O)NC(=O)N >1000 0.874 178.2 Train Neutral NEG PHENELZINE c1ccc(cc1)CCNN >897.2 1.033 136.2 Test Neutral NEG PHENETHICILLIN CC(C(=O)N[C@H]1[C@@H]2N(C1=O <10 2.253 364.4 Test Acid POS )[C@H](C(S2)(C)C)C(=O)O)Oc3ccccc 3 PHENFORMIN c1ccc(cc1)CCNC(=N)NC(=N)N >1000 -0.669 205.3 Train Base NEG PHENIRAMINE MALEATE CN(C)CCC(c1ccccc1)c2ccccn2 >1000 2.435 240.3 Train Base NEG PHENSUXIMIDE CN1C(=O)CC(C1=O)c2ccccc2 >1000 0.942 189.2 Test Neutral NEG PHENTOLAMINE Cc1ccc(cc1)N(CC2=NCCN2)c3cccc(c >1000 3.809 281.4 Test Base NEG 3)O PHENYLMERCURY <10 0.711 336.7 Train Neutral POS ACETATE CC(=O)O[Hg]c1ccccc1 PHTHALYLSULFACETAMIDE CC(=O)NS(=O)(=O)c1ccc(cc1)NC(=O) >1000 -0.445 362.4 Test Acid NEG c2ccccc2C(=O)O PHYTOMENADIONE >1000 12.01 450.7 Train Neutral NEG CC1=C(C(=O)c2ccccc2C1=O)C/C=C(\ C)/CCCC(C)CCCC(C)CCCC(C)C PIMOZIDE <10 6.401 461.6 Train Base POS c1ccc2c(c1)[nH]c(=O)n2C3CCN(CC3) CCCC(c4ccc(cc4)F)c5ccc(cc5)F PIOGLITAZONE CCc1ccc(nc1)CCOc2ccc(cc2)CC3C(= 0.2621 3.533 356.4 Train Neutral POS O)NC(=O)S3 PIPERACILLIN 197.4 1.697 517.6 Train Acid POS CCN1CCN(C(=O)C1=O)C(=O)NC(c2c cccc2)C(=O)N[C@H]3[C@@H]4N(C3 =O)[C@H](C(S4)(C)C)C(=O)O PIPERONYL BUTOXIDE CCCCOCCOCCOCc1cc2c(cc1CCC)O <10 4.479 338.4 Train Neutral POS CO2 PIRACETAM C1CC(=O)N(C1)CC(=O)N >1000 -1.182 142.2 Test Neutral NEG PIRENZEPINE CN1CCN(CC1)CC(=O)N2c3ccccc3C( >1000 -0.349 351.4 Test Base NEG =O)Nc4c2nccc4 PIRETANIDE c1ccc(cc1)Oc2c(cc(cc2S(=O)(=O)N)C( >790.6 2.497 362.4 Train Acid NEG =O)O)N3CCCC3 PRACTOLOL >1000 0.755 266.3 Train Base NEG CC(C)NCC(COc1ccc(cc1)NC(=O)C)O PRAZIQUANTEL c1ccc2c(c1)CCN3C2CN(CC3=O)C(=O 60.27 3.36 312.4 Train Neutral POS )C4CCCCC4 PRIMAQUINE CC(CCCN)Nc1cc(cc2c1nccc2)OC 53.12 2.598 259.4 Test Base POS PROBENECID CCCN(CCC)S(=O)(=O)c1ccc(cc1)C(= 586.8 3.371 285.4 Test Acid NEG O)O PROBUCOL CC(C)(C)c1cc(cc(c1O)C(C)(C)C)SC(C >1000 10.97 516.9 Train Neutral NEG )(C)Sc2cc(c(c(c2)C(C)(C)C)O)C(C)(C) C PROCAINE CCN(CC)CCOC(=O)c1ccc(cc1)N >1000 2.538 236.3 Test Base NEG PROCHLORPERAZINE CN1CCN(CC1)CCCN2c3ccccc3Sc4c2 <10 4.382 374 Train Base POS cc(cc4)Cl PROGESTERONE CC(=O)[C@H]1CC[C@@H]2[C@@]1( <10 3.965 314.5 Train Neutral POS CC[C@H]3[C@H]2CCC4=CC(=O)CC[ C@]34C)C PROPAFENONE CCCNCC(COc1ccccc1C(=O)CCc2ccc 53.7 3.636 341.4 Test Base POS cc2)O PROPANTHELINE BROMIDE CC(C)[N+](C)(CCOC(=O)C1c2ccccc2 291.3 1.493 368.5 Train Cationic POS Oc3c1cccc3)C(C)C PROPRANOLOL CC(C)NCC(COc1cccc2c1cccc2)O >1000 2.753 259.3 Train Base NEG PROTOKYLOL CC(Cc1ccc2c(c1)OCO2)NCC(c3ccc(c( >982.3 1.686 331.4 Train Base NEG HYDROCHLORIDE c3)O)O)O PROTRIPTYLINE 128.6 4.865 263.4 Train Base POS CNCCCC1c2ccccc2C=Cc3c1cccc3 PROXICROMIL CCCc1c2c(c(c3c1oc(cc3=O)C(=O)O) 30.48 5.026 302.3 Train Acid POS O)CCCC2 PS-291822 CC[C@H](c1ccc(o1)C)Nc2c(c(=O)c2= <10 1.463 397.4 Train Acid POS O)Nc3cccc(c3O)C(=O)N(C)C PTK-787 c1ccc2c(c1)c(nnc2Nc3ccc(cc3)Cl)Cc4 <10 4.848 346.8 Test Neutral POS ccncc4 PYRIDOSTIGMINE BROMIDE C[n+]1cccc(c1)OC(=O)N(C)C >1000 -4.264 181.2 Test Cationic NEG PYRIMETHAMINE CCc1c(c(nc(n1)N)N)c2ccc(cc2)Cl 200.1 3.003 248.7 Test Neutral POS QUILOSTIGMINE <10 4.335 377.5 Test Base POS C[C@@]12CCN([C@@H]1N(c3c2cc(c c3)OC(=O)N4CCc5ccccc5C4)C)C QUINACRINE CCN(CC)CCCC(C)Nc1c2ccc(cc2nc3c 101.1 6.723 400 Train Base POS 1cc(cc3)OC)Cl RALFINAMIDE C[C@@H](C(=O)N)NCc1ccc(cc1)OCc 174.7 2.49 302.3 Train Base POS 2ccccc2F RAMATROBAN 62.4 3.972 416.5 Train Acid POS c1ccc2c(c1)c3c(n2CCC(=O)O)CC[C@ H](C3)NS(=O)(=O)c4ccc(cc4)F RAMELTEON CCC(=O)NCC[C@@H]1CCc2c1c3c(c 85.37 2.485 259.3 Test Neutral POS c2)OCC3 REMACEMIDE 288.1 2.552 268.4 Test Base POS CC(Cc1ccccc1)(c2ccccc2)NC(=O)CN REMOXIPRIDE CCN1CCC[C@H]1CNC(=O)c2c(ccc(c <10 3.254 371.3 Train Base POS 2OC)Br)OC RESERPINE COc1ccc2c(c1)[nH]c3c2CCN4[C@@H <10 3.859 608.7 Train Base POS ]3C[C@H]5[C@@H](C4)C[C@H]([C@ @H]([C@H]5C(=O)OC)OC)OC(=O)c6 cc(c(c(c6)OC)OC)OC RILUZOLE c1cc2c(cc1OC(F)(F)F)sc(n2)N 139 3.235 234.2 Train Neutral POS RIMONABANT Cc1c(n(nc1C(=O)NN2CCCCC2)c3ccc( <10 6.471 463.8 Train Neutral POS cc3Cl)Cl)c4ccc(cc4)Cl RISPERIDONE Cc1c(c(=O)n2c(n1)CCCC2)CCN3CCC <10.25 2.711 410.5 Test Base POS (CC3)c4c5ccc(cc5on4)F RO 1130830 c1cc(ccc1Oc2ccc(cc2)Cl)S(=O)(=O)C 23.36 1.852 425.9 Train Neutral POS C3(CCOCC3)C(=O)NO ROFECOXIB CS(=O)(=O)c1ccc(cc1)C2=C(C(=O)O 95.36 1.798 314.4 Train Neutral POS C2)c3ccccc3 ROPIVACAINE CCCN1CCCC[C@H]1C(=O)Nc2c(cccc 646.4 3.162 274.4 Train Base NEG 2C)C ROSIGLITAZONE CN(CCOc1ccc(cc1)CC2C(=O)NC(=O) 6.362 3.02 357.4 Test Neutral POS S2)c3ccccn3 ROXARSONE c1cc(c(cc1[As](=O)(O)O)[N+](=O)[O- >1000 -0.233 263 Train Acid NEG ])O SALICIN >1000 -1.059 286.3 Train Neutral NEG c1ccc(c(c1)CO)O[C@H]2[C@@H]([C @H]([C@@H]([C@H](O2)CO)O)O)O Salicylamide c1ccc(c(c1)C(=O)N)O >1000 1.277 137.1 Train Acid NEG SALSALATE c1ccc(c(c1)C(=O)Oc2ccccc2C(=O)O) >1000 3.334 258.2 Train Acid NEG O SCOPOLAMINE CN1C2CC(CC1C3C2O3)OC(=O)C(CO >1000 0.29 303.4 Train Base NEG )c4ccccc4 SEMATILIDE CCN(CC)CCNC(=O)c1ccc(cc1)NS(=O >1000 1.363 313.4 Test Zwitterion NEG )(=O)C SERATRODAST CC1=C(C(=O)C(=C(C1=O)C)C(CCCC <14.31 4.95 354.4 Train Acid POS CC(=O)O)c2ccccc2)C SERTRALINE CN[C@H]1CC[C@H](c2c1cccc2)c3cc 29.34 5.347 306.2 Train Base POS c(c(c3)Cl)Cl SIBENADET c1ccc(cc1)CCOCCCS(=O)(=O)CCNC <10 2.453 464.6 Test Base POS Cc2ccc(c3c2sc(=O)[nH]3)O SILDENAFIL 16.43 1.981 474.6 Train Base POS CCCc1c2c(c(=O)[nH]c(n2)c3cc(ccc3O CC)S(=O)(=O)N4CCN(CC4)C)n(n1)C SIROLIMUS <10 7.039 914.2 Test Neutral POS C[C@@H]1CC[C@H]2C[C@@H](/C( =C/C=C/C=C/[C@H](C[C@H](C(=O)[ C@@H]([C@@H](/C(=C/[C@H](C(=O )C[C@H](OC(=O)[C@@H]3CCCCN3 C(=O)C(=O)[C@@]1(O2)O)[C@H](C) C[C@@H]4CC[C@H]([C@@H](C4)O C)O)C)/C)O)OC)C)C)/C)OC SITAGLIPTIN c1c(c(cc(c1F)F)F)C[C@H](CC(=O)N2 147.5 0.691 407.3 Test Base POS CCn3c(nnc3C(F)(F)F)C2)N SIVELESTAT CC(C)(C)C(=O)Oc1ccc(cc1)S(=O)(=O) 142.2 2.771 434.5 Train Acid POS Nc2ccccc2C(=O)NCC(=O)O SODIUM ARSANILATE c1cc(ccc1N)[As](=O)(O)O >1000 -1.172 217.1 Train Acid NEG SODIUM FUSIDATE <10 7.284 516.7 Test Acid POS C[C@H]1[C@@H]2CC[C@]3([C@H]([ C@]2(CC[C@H]1O)C)[C@@H](C[C@ @H]\4[C@@]3(C[C@@H](/C4=C(/CC C=C(C)C)\C(=O)O)OC(=O)C)C)O)C SPIPERONE c1ccc(cc1)N2CNC(=O)C23CCN(CC3) <10 2.815 395.5 Test Base POS CCCC(=O)c4ccc(cc4)F SPIRAPRIL CCOC(=O)[C@H](CCc1ccccc1)N[C@ 47.11 1.046 466.6 Train Zwitterion POS HYDROCHLORIDE @H](C)C(=O)N2CC3(C[C@H]2C(=O) O)SCCS3 SU11248 CCN(CC)CCNC(=O)c1c(c([nH]c1C)/C 45.81 2.998 398.5 Test Base POS =C\2/c3cc(ccc3NC2=O)F)C SUCCINYLSULFATHIAZOLE c1cc(ccc1NC(=O)CCC(=O)O)S(=O)(= >1000 0.727 355.4 Train Acid NEG O)Nc2nccs2 SULFACETAMIDE CC(=O)NS(=O)(=O)c1ccc(cc1)N >1000 -0.976 214.2 Train Acid NEG SULFACHLORPYRIDAZINE >1000 0.706 284.7 Test Acid NEG c1cc(ccc1N)S(=O)(=O)Nc2ccc(nn2)Cl SULFADIAZINE >1000 0.1 250.3 Train Acid NEG c1cnc(nc1)NS(=O)(=O)c2ccc(cc2)N SULFADIMETHOXINE COc1cc(nc(n1)OC)NS(=O)(=O)c2ccc( >1000 1.981 310.3 Train Acid NEG cc2)N SULFADIMIDINE Cc1cc(nc(n1)NS(=O)(=O)c2ccc(cc2)N) >1000 1.097 278.3 Test Acid NEG C SULFADOXINE COc1c(ncnc1OC)NS(=O)(=O)c2ccc(cc >1000 1.231 310.3 Train Acid NEG 2)N SULFAMERAZINE >1000 0.599 264.3 Train Acid NEG Cc1ccnc(n1)NS(=O)(=O)c2ccc(cc2)N SULFAMETHIZOLE >1000 0.418 270.3 Train Acid NEG Cc1nnc(s1)NS(=O)(=O)c2ccc(cc2)N SULFAMETHOXAZOLE >1000 0.563 253.3 Test Acid NEG Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N SULFISOXAZOLE >1000 0.222 267.3 Train Acid NEG Cc1c(noc1NS(=O)(=O)c2ccc(cc2)N)C SULINDAC CC\1=C(c2cc(ccc2/C1=C\c3ccc(cc3)S 63.69 3.157 356.4 Train Acid POS (=O)C)F)CC(=O)O SULPIRIDE CCN1CCCC1CNC(=O)c2cc(ccc2OC)S 276.2 1.11 341.4 Train Base POS (=O)(=O)N SURAMIN 107 -8.579 1297 Test Acid POS Cc1ccc(cc1NC(=O)c2cccc(c2)NC(=O) Nc3cccc(c3)C(=O)Nc4cc(ccc4C)C(=O) Nc5ccc(c6c5c(cc(c6)S(=O)(=O)O)S(= O)(=O)O)S(=O)(=O)O)C(=O)Nc7ccc(c 8c7c(cc(c8)S(=O)(=O)O)S(=O)(=O)O) S(=O)(=O)O TACRINE c1ccc2c(c1)c(c3c(n2)CCCC3)N >1000 3.274 198.3 Train Neutral NEG TALNIFLUMATE c1ccc2c(c1)C(OC2=O)OC(=O)c3cccn >1000 5.085 414.3 Test Neutral NEG c3Nc4cccc(c4)C(F)(F)F TAMOXIFEN CC/C(=C(\c1ccccc1)/c2ccc(cc2)OCCN <10 6.818 371.5 Train Base POS (C)C)/c3ccccc3 TELENZEPINE Cc1c2c(cs1)C(=O)Nc3ccccc3N2C(=O) 315.3 0.657 370.5 Train Base NEG CN4CCN(CC4)C TERFENADINE <17.47 6.073 471.7 Test Base POS CC(C)(C)c1ccc(cc1)C(CCCN2CCC(C C2)C(c3ccccc3)(c4ccccc4)O)O TETRACAINE 512.9 3.834 264.4 Train Base NEG CCCCNc1ccc(cc1)C(=O)OCCN(C)C TETROQUINONE C1(=C(C(=O)C(=C(C1=O)O)O)O)O >1000 -1.849 172.1 Train Acid NEG THALIDOMIDE c1ccc2c(c1)C(=O)N(C2=O)C3CCC(=O >1000 0.528 258.2 Test Neutral NEG )NC3=O THIABENDAZOLE c1ccc2c(c1)[nH]c(n2)c3cscn3 560 2.358 201.3 Train Neutral NEG THIORIDAZINE CN1CCCCC1CCN2c3ccccc3Sc4c2cc( 24.33 6.003 370.6 Train Base POS cc4)SC THIOTEPA C1CN1P(=S)(N2CC2)N3CC3 >1000 0.524 189.2 Train Neutral NEG THIOTHIXENE CN1CCN(CC1)CC/C=C\2/c3ccccc3Sc 30.4 3.228 443.6 Train Base POS 4c2cc(cc4)S(=O)(=O)N(C)C TICLOPIDINE 26.95 4.388 263.8 Train Base POS c1ccc(c(c1)CN2CCc3c(ccs3)C2)Cl TIPREDANE <10 4.115 410.6 Train Neutral POS CCS[C@@]1(CC[C@@H]2[C@@]1(C [C@@H]([C@]3([C@H]2CCC4=CC(= O)C=C[C@@]43C)F)O)C)SC TOLAZAMIDE Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2CC 285.7 1.338 311.4 Train Acid POS CCCC2 TOLAZOLINE c1ccc(cc1)CC2=NCCN2 >1000 2.652 160.2 Train Base NEG TOLBUTAMIDE >1000 2.497 270.4 Train Acid NEG CCCCNC(=O)NS(=O)(=O)c1ccc(cc1)C TOLCAPONE Cc1ccc(cc1)C(=O)c2cc(c(c(c2)O)O)[N <33.92 3.245 273.2 Train Acid POS +](=O)[O-] TOLNAFTATE Cc1cccc(c1)N(C)C(=S)Oc2ccc3ccccc3 <10.32 5.339 307.4 Test Neutral POS c2 TOLRESTAT CN(CC(=O)O)C(=S)c1cccc2c1ccc(c2 185.3 3.431 357.4 Test Acid POS C(F)(F)F)OC TORSEMIDE Cc1cccc(c1)Nc2ccncc2S(=O)(=O)NC( 130.7 3.358 348.4 Train Acid POS =O)NC(C)C TRAPIDIL CCN(CC)c1cc(nc2n1ncn2)C 627.8 1.752 205.3 Test Neutral NEG TRETINOIN CC1=C(C(CCC1)(C)C)/C=C/C(=C/C= <10 6.744 300.4 Train Acid POS C/C(=C/C(=O)O)/C)/C TRIFLUOPERAZINE CN1CCN(CC1)CCCN2c3ccccc3Sc4c2 <10 4.692 407.5 Train Base POS cc(cc4)C(F)(F)F TRIFLUPERIDOL c1cc(cc(c1)C(F)(F)F)C2(CCN(CC2)CC 19.7 4.019 409.4 Train Base POS CC(=O)c3ccc(cc3)F)O TRIFLUPROMAZINE CN(C)CCCN1c2ccccc2Sc3c1cc(cc3)C 39.01 5.61 352.4 Train Base POS (F)(F)F TRIMEBUTINE CCC(COC(=O)c1cc(c(c(c1)OC)OC)O <10 4.258 387.5 Test Base POS C)(c2ccccc2)N(C)C TRIMEPRAZINE 73.72 4.798 298.5 Train Base POS CC(CN1c2ccccc2Sc3c1cccc3)CN(C)C TRIMETHOPRIM 833.1 0.981 290.3 Train Base NEG COc1cc(cc(c1OC)OC)Cc2cnc(nc2N)N TRIMETOZINE COc1cc(cc(c1OC)OC)C(=O)N2CCOC >1000 0.275 281.3 Test Neutral NEG C2 TRIOXSALEN Cc1cc(=O)oc2c1cc3cc(oc3c2C)C >525.1 3.469 228.2 Train Neutral NEG TRIPROLIDINE Cc1ccc(cc1)/C(=C\CN2CCCC2)/c3ccc 290.8 3.634 278.4 Train Base POS cn3 TROGLITAZONE 6.9 5.585 441.5 Train Neutral POS Cc1c(c2c(c(c1O)C)CCC(O2)(C)COc3c cc(cc3)CC4C(=O)NC(=O)S4)C TROPICAMIDE CCN(Cc1ccncc1)C(=O)C(CO)c2ccccc 150.9 1.181 284.4 Test Neutral POS 2 TULOBUTEROL CC(C)(C)NCC(c1ccccc1Cl)O >1000 2.529 227.7 Test Base NEG URAPIDIL Cn1c(cc(=O)n(c1=O)C)NCCCN2CCN( <11.3 2.443 387.5 Test Base POS CC2)c3ccccc3OC UTIBAPRIL CCOC(=O)[C@H](CCc1ccccc1)N[C@ <13.51 2.211 449.6 Test Zwitterion POS @H](C)C(=O)N2[C@@H](SC(=N2)C( C)(C)C)C(=O)O VALPROIC ACID CCCC(CCC)C(=O)O >1000 2.76 144.2 Train Acid NEG VENLAFAXINE CN(C)CC(c1ccc(cc1)OC)C2(CCCCC2) >1000 3.269 277.4 Train Base NEG O VERAPAMIL CC(C)C(CCCN(C)CCc1ccc(c(c1)OC)O 20.5 4.466 454.6 Train Base POS HYDROCHLORIDE C)(C#N)c2ccc(c(c2)OC)OC VX 745 c1cc(c(c(c1)Cl)c2c3ccc(nn3cnc2=O)S <10 5.467 436.3 Test Neutral POS c4ccc(cc4F)F)Cl WARFARIN CC(=O)CC(c1ccccc1)c2c(c3ccccc3oc 115.3 2.901 308.3 Train Neutral POS 2=O)O XALIPRODEN c1ccc2cc(ccc2c1)CCN3CCC(=CC3)c4 117.1 6.669 381.4 Train Base POS cccc(c4)C(F)(F)F XANTRYL <10 9.04 973.7 Train Acid POS c1c2c(c(c(c1I)O)I)Oc3c(cc(c(c3I)O)I)C 24c5c(c(c(c(c5Cl)Cl)Cl)Cl)C(=O)O4 XYLAZINE Cc1cccc(c1NC2=NCCCS2)C >1000 0.52 220.3 Test Base NEG XYLOMETAZOLINE >796.1 5.376 244.4 Test Base NEG Cc1cc(cc(c1CC2=NCCN2)C)C(C)(C)C ZD-2486 C[C@H](CC(=O)O)COc1ccc(cc1)N2C >1000 3.041 355.4 Test Acid NEG CN(CC2)c3ccncc3 ZD-2574 Cc1cnc(c(n1)OC)NS(=O)(=O)c2cccnc 19.45 5.495 412.5 Train Acid POS 2c3ccc(cc3)CC(C)C ZD-6169 C[C@](C(=O)Nc1ccc(cc1)C(=O)c2ccc 21.39 3.786 337.3 Train Neutral POS cc2)(C(F)(F)F)O ZD-9379 Cc1cc(ccc1n2c(=O)c3c(c(=O)[nH]2)[n 490 1.842 383.8 Test Neutral NEG H]c4cc(ccc4c3=O)Cl)OC ZD-9583 Cc1ccc(c(c1)C#N)OC(C)(C)[C@H]2O <10 3.336 450.5 Train Acid POS C[C@H]([C@H](O2)c3cccnc3)C/C=C\ CCC(=O)O ZILEUTON CC(c1cc2ccccc2s1)N(C(=O)N)O >751.2 2.483 236.3 Train Neutral NEG ZIMELDINE 229.7 3.194 317.2 Train Base POS CN(C)C/C=C(/c1ccc(cc1)Br)\c2cccnc2 ZOXAZOLAMINE c1cc2c(cc1Cl)nc(o2)N >1000 1.893 168.6 Train Neutral NEG