Structure–based identification of OATP1B1/3 inhibitors Tom De Bruyn, Gerard J.P. Van Westen, Adriaan P. IJzerman, Bruno Stieger, Peter de Witte, Patrick F. Augustijns and Pieter P. Annaert Molecular Pharmacology Complete dataset on % inhibition of sodium fluorescein (10 µM) uptake in OATP1B1 and OATP1B3-transfected CHO cells by all compounds (10 µM) used for building the in silico model. For compounds tested at different concentrations, pIC50 values are also shown. Compound name percent_of_control_1B3 percent_of_control_1B1 Smiles InChI InChIKey pIC50_1B3 pIC50_1B1 CARMINIC ACID 121.8970734 21.61023724 c(c1O[H])(C2=O)c(c(c([O-])c1O[C@@]3([H])O[C@]([H])(C([H])([H])O[H])[C@]([H])([C@]([H])(O[H])[C@@]3([H])O[H])O[H])O[H])C(c(c([H])c(O[H])c4C([O-])=O)c2c4C([H])([H])[H])=O InChI=1S/C22H20O14/c1-4-8-5(2-6(24)9(4)21(33)34)12(25)10-11(14(8)27)16(29)20(18(31)15(10)28)36-22-19(32)17(30)13(26)7(3-23)35-22/h2,7,13,17,19,22-24,26,28-32H,3H2,1H3,(H,33,34)/p-2/t7-,13-,17+,19-,22-/m1/s1 FTZKEIWUUDUSNG-UZYNOIPLSA-L 3,7-DIMETHOXYFLAVONE 144.5632333 59.2805931 C(OC([H])([H])[H])(C(=O)c(c([H])c([H])c(c1[H])OC([H])([H])[H])c1O2)=C2c3c([H])c([H])c([H])c([H])c3[H] InChI=1S/C17H14O4/c1-19-12-8-9-13-14(10-12)21-16(17(20-2)15(13)18)11-6-4-3-5-7-11/h3-10H,1-2H3 CNDZOPXQZSXGSK-UHFFFAOYSA-N CARNOSINE 98.8638076 26.43693974 n1c([H])n([H])c([H])c1C([H])([H])[C@]([H])(N([H])C(=O)C([H])([H])C([H])([H])[N+]([H])([H])[H])C([O-])=O InChI=1S/C9H14N4O3/c10-2-1-8(14)13-7(9(15)16)3-6-4-11-5-12-6/h4-5,7H,1-3,10H2,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1 CQOVPNPJLQNMDC-ZETCQYMHSA-N KARANJIN 124.739521 50.38982717 C1([O-])=C(c2c([H])c([H])c([H])c([H])c2[H])Oc(c3C1=O)c([H])c([H])c(oc4[H])c3c4[H] InChI=1S/C17H10O4/c18-15-14-11-8-9-20-12(11)6-7-13(14)21-17(16(15)19)10-4-2-1-3-5-10/h1-9,19H/p-1 RFTCASQIXQHXFX-UHFFFAOYSA-M 6,4'-DIMETHOXYFLAVONE 110.4433729 34.4446499 C(c1c([H])c([H])c(c([H])c1[H])OC([H])([H])[H])(Oc(c([H])c([H])c(c2[H])OC([H])([H])[H])c2C3=O)=C3[H] InChI=1S/C17H14O4/c1-19-12-5-3-11(4-6-12)17-10-15(18)14-9-13(20-2)7-8-16(14)21-17/h3-10H,1-2H3 ANVFDWBCVDQNEZ-UHFFFAOYSA-N BERGENIN 94.52147061 14.58593007 c12c(c([H])c(O[H])c(OC([H])([H])[H])c1O[H])C(=O)O[C@@]([H])([C@]([H])([C@]([H])(O[H])[C@@]([H])(C([H])([H])O[H])O3)O[H])[C@@]23[H] InChI=1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12-,13+/m1/s1 YWJXCIXBAKGUKZ-BPTACTMOSA-N 7,2'-DIMETHOXYFLAVONE 110.459106 95.81702508 C1(c2c([H])c([H])c([H])c([H])c2OC([H])([H])[H])=C([H])C(c(c([H])c([H])c(OC([H])([H])[H])c3[H])c3O1)=O InChI=1S/C17H14O4/c1-19-11-7-8-12-14(18)10-17(21-16(12)9-11)13-5-3-4-6-15(13)20-2/h3-10H,1-2H3 WVWDHKIZBHIGJE-UHFFFAOYSA-N CARYLOPHYLLENE OXIDE 80.12043514 54.10267524 C1(C([H])([H])[H])(C([H])([H])C2([H])[H])C([H])(O1)C([H])([H])C([C@@]([H])(C([H])([H])C3(C([H])([H])[H])C([H])([H])[H])[C@@]23[H])=C([H])[H] InChI=1S/C14H22O/c1-9-7-12-14(4,15-12)6-5-11-10(9)8-13(11,2)3/h10-12H,1,5-8H2,2-4H3/t10-,11-,12?,14?/m1/s1 AMTSLHRSERHBCF-IBQNZTRDSA-N URSOCHOLANIC ACID 102.6659746 98.44612291 [C@@]1(C([H])([H])[H])(C([H])([H])C2([H])[H])C([H])(C([H])([H])C([H])([H])[C@]1([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([O-])=O)C([H])(C23[H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])C([H])([H])C([H])([H])C4([H])[H])[C@@]34C([H])([H])[H] InChI=1S/C24H40O2/c1-16(7-12-22(25)26)19-10-11-20-18-9-8-17-6-4-5-14-23(17,2)21(18)13-15-24(19,20)3/h16-21H,4-15H2,1-3H3,(H,25,26)/p-1/t16?,17-,18?,19+,20?,21?,23-,24+/m0/s1 RPKLZQLYODPWTM-UHJJYCRNSA-M CHOLEST-5-EN-3-ONE 103.4578743 119.6796 [C@@]1(C([H])([H])[H])(C([H])([H])C2([H])[H])C([H])(C([H])([H])C([H])([H])[C@]1([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])(C23[H])C([H])([H])C([H])=C(C([H])([H])C(=O)C([H])([H])C4([H])[H])[C@@]34C([H])([H])[H] InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,22-25H,6-8,10-17H2,1-5H3/t19?,22?,23-,24?,25?,26+,27-/m1/s1 GGCLNOIGPMGLDB-IVFFKYSXSA-N [C@@]1([H])(O[C@]([H])([C@@]([H])(N([H])[H])C([H])([H])[C@]([H])([C@]2([H])O[C@@]3([H])O[C@]([H])(C([H])([H])O[H])[C@]([H])([C@]([H])(N([H])[H])[C@@]3([H])O[H])O[H])N([H])[H])[C@]2([H])O[H])O[C@@]([H])([C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])[N+]([H])([H])[H])C([H])([H])N([H] BEKANAMYCIN SULFATE 118.1211282 101.9281723 )[H] InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/p+1/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1 SKKLOUVUUNMCJE-FQSMHNGLSA-O CITRULLINE 119.6734612 135.0929369 C(N([H])[H])(N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([N+]([H])([H])[H])C([O-])=O)=O InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12) RHGKLRLOHDJJDR-UHFFFAOYSA-N GENKWANIN 107.0397778 116.7093215 c12c(c([H])c(OC([H])([H])[H])c([H])c1[O-])OC(=C([H])C2=O)c3c([H])c([H])c(c([H])c3[H])[O-] InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3/p-2 JPMYFOBNRRGFNO-UHFFFAOYSA-L S-ISOCORYDINE (+) 102.1415378 115.2241823 c(c(C([H])([H])C([H])([H])N1C([H])([H])[H])c([H])c(c2OC([H])([H])[H])OC([H])([H])[H])([C@]1([H])C([H])([H])c(c34)c([H])c([H])c(OC([H])([H])[H])c3O[H])c24 InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)20(25-4)18-16(12)13(21)9-11-5-6-14(23-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1 QELDJEKNFOQJOY-ZDUSSCGKSA-N 4-METHYLESCULETIN 110.1129777 121.7467532 c1(OC(=O)C([H])=C2C([H])([H])[H])c2c([H])c(O[H])c([O-])c1[H] InChI=1S/C10H8O4/c1-5-2-10(13)14-9-4-8(12)7(11)3-6(5)9/h2-4,11-12H,1H3/p-1 KVOJTUXGYQVLAJ-UHFFFAOYSA-M [C@@]1(C([H])([H])[H])(C([H])([H])C([H])([H])[C@@](C23[H])(C([H])([H])O[H])C([H])([H])C([H])([H])[C@@]2([H])C(C([H])([H])[H])=C([H])[H])[C@@]3([H])C([H])([H])C([H])([H])C4([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C5([H])[C@@]4(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(O[H])C5(C([H] BETULIN 92.42896764 106.3233817 )([H])[H])C([H])([H])[H] InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21-,22?,23?,24-,25?,27+,28-,29-,30+/m0/s1 FVWJYYTZTCVBKE-BGYIOJQESA-N OBTUSAQUINONE 88.38031528 60.32420445 C([H])(C1=O)=C(OC([H])([H])[H])\C(\C([H])=C1O[H])=C([H])\C([H])=C([H])\c2c([H])c([H])c([H])c([H])c2[H] InChI=1S/C16H14O3/c1-19-16-11-15(18)14(17)10-13(16)9-5-8-12-6-3-2-4-7-12/h2-11,17H,1H3/b8-5+,13-9+ LUZUAYAKZLCOCQ-BHHNFLQBSA-N HEMATEIN 73.22409077 65.79312931 C1(C2=C([H])C(=O)C(O[H])=C1[H])=C3[C@@](C2([H])[H])(O[H])C([H])([H])Oc4c3c([H])c([H])c(c4[O-])O[H] InChI=1S/C16H12O6/c17-10-2-1-8-13-9-4-12(19)11(18)3-7(9)5-16(13,21)6-22-15(8)14(10)20/h1-4,17,19-21H,5-6H2/p-1/t16-/m0/s1 HLUCICHZHWJHLL-INIZCTEOSA-M 2-ACETYLPYRROLE 98.28692708 111.7120287 c1(c([H])c([H])c([H])n1[H])C(C([H])([H])[H])=O InChI=1S/C6H7NO/c1-5(8)6-3-2-4-7-6/h2-4,7H,1H3 IGJQUJNPMOYEJY-UHFFFAOYSA-N CONIINE 100.1277004 105.3399787 [N+]1([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])[H] InChI=1S/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3/p+1/t8-/m1/s1 NDNUANOUGZGEPO-MRVPVSSYSA-O ANABASAMINE HYDROCHLORIDE 108.2145164 100.0316094 [NH+]1(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])c(c([H])c([H])c(n2)c(c([H])c([H])c([H])n3)c3[H])c2[H])C([H])([H])[H] InChI=1S/C16H19N3/c1-19-10-3-2-6-16(19)14-7-8-15(18-12-14)13-5-4-9-17-11-13/h4-5,7-9,11-12,16H,2-3,6,10H2,1H3/p+1 TZRDBHMKTWECOV-UHFFFAOYSA-O DIHYDROROTENONE 63.71080659 53.61097374 c1(O[C@]([H])(C([H])([H])Oc(c23)c([H])c(c(OC([H])([H])[H])c2[H])OC([H])([H])[H])[C@]3(C4=O)[H])c4c([H])c([H])c5c1C([H])([H])C([H])(O5)C([H])(C([H])([H])[H])C([H])([H])[H] InChI=1S/C23H24O6/c1-11(2)16-8-14-15(28-16)6-5-12-22(24)21-13-7-18(25-3)19(26-4)9-17(13)27-10-20(21)29-23(12)14/h5-7,9,11,16,20-21H,8,10H2,1-4H3/t16?,20-,21+/m1/s1 DTFARBHXORYQBF-XHEPWMPHSA-N SELINIDIN 152.9804445 165.0566243 c1(C([H])([H])[C@@]([H])(OC(=O)\C(\C([H])([H])[H])=C([H])/C([H])([H])[H])C(O2)(C([H])([H])[H])C([H])([H])[H])c2c([H])c([H])c(c13)C([H])=C([H])C(=O)O3 InChI=1S/C19H20O5/c1-5-11(2)18(21)22-15-10-13-14(24-19(15,3)4)8-6-12-7-9-16(20)23-17(12)13/h5-9,15H,10H2,1-4H3/b11-5-/t15-/m1/s1 RRHCDWLSHIIIIT-NVWZYQMFSA-N PTERYXIN 114.2927393 84.79889756 c12c(c([H])c([H])c(C([H])=C([H])C(=O)O3)c13)OC([C@]([H])(OC(C([H])([H])[H])=O)[C@]2([H])OC(=O)\C(\C([H])([H])[H])=C([H])\C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] InChI=1S/C21H22O7/c1-6-11(2)20(24)27-18-16-14(28-21(4,5)19(18)25-12(3)22)9-7-13-8-10-15(23)26-17(13)16/h6-10,18-19H,1-5H3/b11-6+/t18-,19-/m1/s1 LYUZYPKZQDYMEE-CCGSVPMNSA-N CYTIDINE 114.0252765 99.43956064 N1(C([H])=C([H])C(=NC1=O)N([H])[H])C2([H])O[C@@]([H])([C@@]([H])(O[H])[C@@]2([H])O[H])C([H])([H])O[H] InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7-,8?/m1/s1 UHDGCWIWMRVCDJ-ZRTZXPPTSA-N SAPPANONE A TRIMETHYL ETHER 100.720314 112.0231052 C(/C([H])([H])Oc(c12)c([H])c(c([H])c1[H])OC([H])([H])[H])(=C([H])\c(c([H])c([H])c(c3OC([H])([H])[H])OC([H])([H])[H])c3[H])\C2=O InChI=1S/C19H18O5/c1-21-14-5-6-15-17(10-14)24-11-13(19(15)20)8-12-4-7-16(22-2)18(9-12)23-3/h4-10H,11H2,1-3H3/b13-8- YKRAQIAZPKGEIC-JYRVWZFOSA-N [C@@]1(C([H])([H])[H])(C([H])([H])C2([H])[H])C([H])(C([H])([H])C([H])([H])[C@]1([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])(C([H])([H])C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])(C23[H])C([H])([H])C([H])=C(C([H])([H])[C@]([H])(C([H])([H])C4([H])[H])OC(C([H])([H])[H])=O)[C@@] SITOSTERYL ACETATE 83.77575987 97.72362274 34C([H])([H])[H] InChI=1S/C31H52O2/c1-8-23(20(2)3)10-9-21(4)27-13-14-28-26-12-11-24-19-25(33-22(5)32)15-17-30(24,6)29(26)16-18-31(27,28)7/h11,20-21,23,25-29H,8-10,12-19H2,1-7H3/t21?,23?,25-,26?,27+,28?,29?,30-,31+/m0/s1