CDK 08101821052D 22 25 0 0 1 0 0 0 0 0999 V2000 5.9998 3.5270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1240 3.0521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6999 2.7785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6300 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5300 -0.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6700 -2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2300 0.0600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6300 1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4000 -0.4000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6700 2.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2800 0.8100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2300 -2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9300 -2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5300 -2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9300 -0.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6300 0.0600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6700 -0.6900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9700 0.0600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9700 1.5600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4000 2.0300 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8289 -2.9402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4608 0.5312 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 1 3 0 0 0 0 6 4 1 0 0 0 0 7 5 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 13 4 1 0 0 0 0 13 12 2 0 0 0 0 14 5 2 0 0 0 0 14 12 1 0 0 0 0 15 7 2 0 0 0 0 15 13 1 0 0 0 0 16 8 1 0 0 0 0 16 15 1 0 0 0 0 17 6 1 0 0 0 0 17 16 1 0 0 0 0 18 9 1 0 0 0 0 18 17 1 0 0 0 0 19 2 1 1 0 0 0 19 10 1 0 0 0 0 19 18 1 0 0 0 0 20 3 1 0 0 0 0 20 11 1 6 0 0 0 20 19 1 0 0 0 0 21 14 1 0 0 0 0 20 22 1 1 0 0 0 M END > InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1 > 17-Ethinylestradiol > M01 M02 M03 M04 M05 M06 M07 > M01 M03 M05 M07 > M07 > > M01 NAME: 17-Ethinylestradiol 3-O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C26H32O8/c1-3-26(32)11-9-18-17-6-4-13-12-14(5-7-15(13)16(17)8-10-25(18,26)2)33-24-21(29)19(27)20(28)22(34-24)23(30)31/h1,5,7,12,16-22,24,27-29,32H,4,6,8-11H2,2H3,(H,30,31)/t16?,17?,18?,19?,20?,21?,22?,24?,25-,26-/m0/s1 M02 NAME: 17-Ethinylestradiol 17-O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C26H32O8/c1-3-26(34-24-21(30)19(28)20(29)22(33-24)23(31)32)11-9-18-17-6-4-13-12-14(27)5-7-15(13)16(17)8-10-25(18,26)2/h1,5,7,12,16-22,24,27-30H,4,6,8-11H2,2H3,(H,31,32)/t16?,17?,18?,19?,20?,21?,22?,24?,25-,26-/m0/s1 M03 NAME: 17-Ethinylestradiol, 3-O-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C20H24O5S/c1-3-20(21)11-9-18-17-6-4-13-12-14(25-26(22,23)24)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21H,4,6,8-11H2,2H3,(H,22,23,24)/t16?,17?,18?,19-,20-/m0/s1 M04 NAME: 17-Ethinylestradiol, 16-OH PUBCHEM_CID: NULL INCHI: InChI=1S/C20H24O3/c1-3-20(23)18(22)11-17-16-6-4-12-10-13(21)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,21-23H,4,6,8-9,11H2,2H3/t15?,16?,17?,18?,19-,20-/m0/s1 M05 NAME: 17-Ethinylestradiol, 2-OH PUBCHEM_CID: NULL INCHI: InChI=1S/C20H24O3/c1-3-20(23)9-7-16-14-5-4-12-10-17(21)18(22)11-15(12)13(14)6-8-19(16,20)2/h1,10-11,13-14,16,21-23H,4-9H2,2H3/t13?,14?,16?,19-,20-/m0/s1 M06 NAME: 17-Ethinylestradiol, 4-OH PUBCHEM_CID: NULL INCHI: InChI=1S/C20H24O3/c1-3-20(23)11-9-16-14-4-5-15-12(6-7-17(21)18(15)22)13(14)8-10-19(16,20)2/h1,6-7,13-14,16,21-23H,4-5,8-11H2,2H3/t13?,14?,16?,19-,20-/m0/s1 M07 NAME: 17-Ethinylestradiol, 6-OH PUBCHEM_CID: NULL INCHI: InChI=1S/C20H24O3/c1-3-20(23)9-7-17-15-11-18(22)16-10-12(21)4-5-13(16)14(15)6-8-19(17,20)2/h1,4-5,10,14-15,17-18,21-23H,6-9,11H2,2H3/t14?,15?,17?,18?,19-,20-/m0/s1 M08 NAME: 17-Ethinylestradiol, 3-O-methyl PUBCHEM_CID: NULL INCHI: InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1 > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 11 11 0 0 0 0 0 0 0 0999 V2000 2.5989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 -0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8981 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2981 0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8981 -0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0008 1.4998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3002 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1970 -1.5006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 2 1 0 0 0 0 5 3 2 0 0 0 0 6 1 1 0 0 0 0 7 2 2 0 0 0 0 7 3 1 0 0 0 0 8 4 2 0 0 0 0 8 5 1 0 0 0 0 9 6 2 0 0 0 0 9 7 1 0 0 0 0 10 6 1 4 0 0 0 11 8 1 0 0 0 0 M END > InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10) > Acetaminophen > M01 M02 M03 M04 M05 M06 M07 M08 > M01 M02 M03 M04 M05 M06 M08 > M01 M02 > > M01 NAME: acetic acid PUBCHEM_CID: 21980959 INCHI: InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) M02 NAME: p-aminophenol PUBCHEM_CID: 13283155 INCHI: InChI=1S/C6H7NO/c7-5-1-3-6(8)4-2-5/h1-4,8H,7H2 M03 NAME: p-acetamidophenylglucuronide PUBCHEM_CID: 4022661 INCHI: InChI=1S/C14H17NO8/c1-6(16)15-7-2-4-8(5-3-7)22-14-11(19)9(17)10(18)12(23-14)13(20)21/h2-5,9-12,14,17-19H,1H3,(H,15,16)(H,20,21) M04 NAME: Paracetamol sulfate PUBCHEM_CID: 83939 INCHI: InChI=1S/C8H9NO5S/c1-6(10)9-7-2-4-8(5-3-7)14-15(11,12)13/h2-5H,1H3,(H,9,10)(H,11,12,13) M05 NAME: N-Hydroxyparacetamol PUBCHEM_CID: 45750 INCHI: InChI=1S/C8H9NO3/c1-6(10)9(12)7-2-4-8(11)5-3-7/h2-5,11-12H,1H3 M06 NAME: Acetamide, N-(2,4-dihydroxyphenyl)- PUBCHEM_CID: 580765 INCHI: InChI=1S/C8H9NO3/c1-5(10)9-7-3-2-6(11)4-8(7)12/h2-4,11-12H,1H3,(H,9,10) M07 NAME: Napqi PUBCHEM_CID: 39763 INCHI: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3 M08 NAME: 3-Hydroxyacetaminophen PUBCHEM_CID: 161950 INCHI: InChI=1S/C8H9NO3/c1-5(10)9-6-2-3-7(11)8(12)4-6/h2-4,11-12H,1H3,(H,9,10) > Laine, JE. et al. (2009); Acetaminophen bioactivation by human cytochrome P450 enzymes and animal microsomes; Xenobiotica. 2009 Jan;39(1):11-21. doi: 10.1080/00498250802512830; PMID:19219744 Mugford CA. and Tarloff JB. (1995); Contribution of oxidation and deacetylation to the bioactivation of acetaminophen in vitro in liver and kidney from male and female Sprague-Dawley rats; Drug Metab Dispos. 1995 Feb;23(2):290-4; PMID: 7736927 Bertolini, A. et al. (2006); Paracetamol: new vistas of an old drug; CNS Drug Rev. 2006 Fall-Winter;12(3-4):250-75; PMID:17227290; DOI:10.1111/j.1527-3458.2006.00250.x $$$$ CDK 08101821052D 22 21 0 0 0 0 0 0 0 0999 V2000 -1.2990 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0933 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6913 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6913 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2894 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 3.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2894 6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 3 2 1 0 0 0 0 4 3 1 0 0 0 0 5 4 1 0 0 0 0 6 5 1 0 0 0 0 6 7 2 0 0 0 0 8 7 1 0 0 0 0 9 8 1 0 0 0 0 9 10 2 0 0 0 0 11 10 1 0 0 0 0 12 11 1 0 0 0 0 12 13 2 0 0 0 0 14 13 1 0 0 0 0 15 14 1 0 0 0 0 15 16 2 0 0 0 0 17 16 1 0 0 0 0 18 17 1 0 0 0 0 19 18 1 0 0 0 0 20 19 1 0 0 0 0 21 20 2 0 0 0 0 22 20 1 0 0 0 0 M END > InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15- > Arachidonic acid > M01 M02 M03 M04 M05 M06 M07 M08 M09 M10 M11 M12 M13 M14 M15 M16 M17 M18 M19 M20 > M03 M04 M05 M15 M16 M17 M18 M19 M20 > M03 M15 M16 M17 M18 M19 M20 > > M01 NAME: 1-arachidonoyl-DHAP(2-) PUBCHEM_CID: 86289260 INCHI: InChI=1S/C23H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15- M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C41H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-,18-17- M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C26H40O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(27)33-26-23(30)21(28)22(29)24(34-26)25(31)32/h6-7,9-10,12-13,15-16,21-24,26,28-30H,2-5,8,11,14,17-19H2,1H3,(H,31,32)/b7-6-,10-9-,13-12-,16-15- M04 NAME: (+/-)18-HETE PUBCHEM_CID: 6442778 INCHI: InChI=1S/C20H32O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,19,21H,2-3,8-9,14-18H2,1H3,(H,22,23)/b6-4-,7-5-,12-10-,13-11- M05 NAME: 16-HETE PUBCHEM_CID: 6442739 INCHI: InChI=1S/C20H32O3/c1-2-3-16-19(21)17-14-12-10-8-6-4-5-7-9-11-13-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14- M06 NAME: 7-HETE PUBCHEM_CID: 101925465 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-13-16-19(21)17-14-12-15-18-20(22)23/h6-7,9-10,13-14,16-17,19,21H,2-5,8,11-12,15,18H2,1H3,(H,22,23)/b7-6-,10-9-,16-13-,17-14- M07 NAME: 10-HETE PUBCHEM_CID: 53481450 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-10-13-16-19(21)17-14-11-8-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b7-6-,9-8-,16-13-,17-14- M08 NAME: 13-HETE PUBCHEM_CID: 53481471 INCHI: InChI=1S/C20H32O3/c1-2-3-4-10-13-16-19(21)17-14-11-8-6-5-7-9-12-15-18-20(22)23/h6-9,13-14,16-17,19,21H,2-5,10-12,15,18H2,1H3,(H,22,23)/b8-6-,9-7-,16-13-,17-14- M09 NAME: 9-HETE PUBCHEM_CID: 14123398 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+ M10 NAME: 5-HETE PUBCHEM_CID: NULL INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14? M11 NAME: 12-HETE PUBCHEM_CID: 13786989 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+ M12 NAME: 8-HETE PUBCHEM_CID: NULL INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13? M13 NAME: 15-HETE PUBCHEM_CID: 9966861 INCHI: InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+ M14 NAME: 11-HETE PUBCHEM_CID: NULL INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b9-6-,10-7-,14-11-,16-13? M15 NAME: 19-HETE PUBCHEM_CID: 20839325 INCHI: InChI=1S/C20H32O3/c1-19(21)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20(22)23/h3-6,9-12,19,21H,2,7-8,13-18H2,1H3,(H,22,23)/b5-3-,6-4-,11-9-,12-10- M16 NAME: 5,6-epoxy-8Z,11Z,14Z-eicosatrienoic acid PUBCHEM_CID: 5283202 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,10-9-,13-12- M17 NAME: 8,9-epoxy-5Z,11Z,14Z-eicosatrienoic acid PUBCHEM_CID: 5283203 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-12-15-18-19(23-18)16-13-10-11-14-17-20(21)22/h6-7,9-10,12-13,18-19H,2-5,8,11,14-17H2,1H3,(H,21,22)/b7-6-,12-9-,13-10- M18 NAME: 11,12-epoxy-5Z,8Z,14Z-eicosatrienoic acid PUBCHEM_CID: 5283204 INCHI: InChI=1S/C20H32O3/c1-2-3-4-5-9-12-15-18-19(23-18)16-13-10-7-6-8-11-14-17-20(21)22/h6,8-10,12-13,18-19H,2-5,7,11,14-17H2,1H3,(H,21,22)/b8-6-,12-9-,13-10- M19 NAME: 14,15-epoxy-5Z,8Z,11Z-eicosatrienoic acid PUBCHEM_CID: 5283205 INCHI: InChI=1S/C20H32O3/c1-2-3-12-15-18-19(23-18)16-13-10-8-6-4-5-7-9-11-14-17-20(21)22/h4,6-7,9-10,13,18-19H,2-3,5,8,11-12,14-17H2,1H3,(H,21,22)/b6-4-,9-7-,13-10- M20 NAME: 20-Hydroxyeicosatetraenoic acid PUBCHEM_CID: 5283157 INCHI: InChI=1S/C20H32O3/c21-19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(22)23/h1,3-4,6-7,9-10,12,21H,2,5,8,11,13-19H2,(H,22,23)/b3-1-,6-4-,9-7-,12-10- M21 NAME: (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyicosa-5,8,10,14-tetraenoate PUBCHEM_CID: NULL INCHI: NULL M22 NAME: (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoate PUBCHEM_CID: NULL INCHI: NULL M23 NAME: leukotriene A4 PUBCHEM_CID: NULL INCHI: NULL M24 NAME: Prostaglandin G2 PUBCHEM_CID: NULL INCHI: NULL > ADD PMID:715838 Turgeon D et al. (2003); Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases; J Lipid Res. 2003 Jun;44(6):1182-91. Epub 2003 Mar 16 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 PMID:702629 http://www.uniprot.org/uniprot/P18054 http://www.uniprot.org/uniprot/P16050 http://www.uniprot.org/uniprot/P09917 PMID:727520 $$$$ CDK 08101821052D 14 14 0 0 0 0 0 0 0 0999 V2000 5.1970 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1970 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8983 0.7498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8981 2.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8981 2.2498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 2.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 2.2494 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5006 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5989 2.9996 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5989 2.9996 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 0.7494 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 0.7494 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.9994 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4 1 1 0 0 0 0 5 2 1 0 0 0 0 5 3 1 0 0 0 0 9 6 1 0 0 0 0 10 4 1 4 0 0 0 10 7 2 0 0 0 0 11 5 1 0 0 0 0 11 8 2 0 0 0 0 12 6 2 0 0 0 0 12 7 1 0 0 0 0 13 6 1 0 0 0 0 13 8 1 4 0 0 0 14 7 1 0 0 0 0 14 8 1 0 0 0 0 M END > InChI=1S/C8H14ClN5/c1-4-10-7-12-6(9)13-8(14-7)11-5(2)3/h5H,4H2,1-3H3,(H2,10,11,12,13,14) > Atrazine > M01 M02 M03 M04 M05 M06 > M01 M02 M03 M04 M05 M06 > M02 M03 M04 M05 M06 > M02 M04 M05 M06 > M01 NAME: Atrazine Glutathione PUBCHEM_CID: 4473092 INCHI: InChI=1S/C18H30N8O6S/c1-4-20-16-24-17(22-9(2)3)26-18(25-16)33-8-11(14(30)21-7-13(28)29)23-12(27)6-5-10(19)15(31)32/h9-11H,4-8,19H2,1-3H3,(H,21,30)(H,23,27)(H,28,29)(H,31,32)(H2,20,22,24,25,26) M02 NAME: Desisopropylatrazine (DIA) PUBCHEM_CID: NULL INCHI: InChI=1S/C5H9ClN5/c1-2-8-5-10-3(6)9-4(7)11-5/h2H2,1,7H3,(H,8,9,10,11) M03 NAME: 1-hydroxyisopropylatrazine (HIATZ) PUBCHEM_CID: 5818023 INCHI: InChI=1S/C8H14ClN5O/c1-3-10-7-12-6(9)13-8(14-7)11-5(2)4-15/h5,15H,3-4H2,1-2H3,(H2,10,11,12,13,14) M04 NAME: acetone PUBCHEM_CID: 180 INCHI: InChI=1S/C3H6O/c1-3(2)4/h1-2H3 M05 NAME: acetaldehyde PUBCHEM_CID: NULL INCHI: InChI=1S/C2H4O/c1-2-3/h2H,1H3 M06 NAME: Deethylatrazine PUBCHEM_CID: NULL INCHI: InChI=1S/C6H10ClN5/c1-3(2)9-6-11-4(7)10-5(8)12-6/h3H,1-2H3,(H3,8,9,10,11,12) M07 NAME: 2-hydroxyethylatrazine (HEATZ) PUBCHEM_CID: NULL INCHI: InChI=1/C8H14ClN5O/c1-4(2)10-7-12-6(9)13-8(14-7)11-5(3)15/h4-5,15H,1-3H3,(H2,10,11,12,13,14) > Joo,H. et al. (2010); Human metabolism of atrazine; Pesticide Biochemistry and Physiology 98 (2010) 73–79 $$$$ CDK 08101821052D 15 16 0 0 0 0 0 0 0 0999 V2000 3.7781 5.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7200 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7200 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4200 -1.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1800 -1.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4200 1.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4800 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1200 -1.0200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1200 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1800 1.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4790 3.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4790 4.9800 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7781 2.7300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1800 2.7300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2 0 0 0 0 5 2 1 0 0 0 0 6 4 2 0 0 0 0 7 3 1 0 0 0 0 8 4 1 0 0 0 0 9 5 2 0 0 0 0 9 6 1 0 0 0 0 10 7 2 0 0 0 0 10 9 1 0 0 0 0 11 8 2 0 0 0 0 11 10 1 0 0 0 0 13 1 1 0 0 0 0 13 12 2 0 0 0 0 14 12 1 4 0 0 0 15 11 1 0 0 0 0 15 12 1 0 0 0 0 M END > InChI=1S/C12H11NO2/c1-13-12(14)15-11-8-4-6-9-5-2-3-7-10(9)11/h2-8H,1H3,(H,13,14) > Carbaryl > M01 > M03 > > > M01 NAME: N-(Hydroxymethyl)carbaryl PUBCHEM_CID: 21341 INCHI: InChI=1S/C12H11NO3/c14-8-13-12(15)16-11-7-3-5-9-4-1-2-6-10(9)11/h1-7,14H,8H2,(H,13,15) M02 NAME: 4-hydroxycarbaryl PUBCHEM_CID: NULL INCHI: InChI=1S/C12H11NO3/c1-13-12(15)16-11-7-6-10(14)8-4-2-3-5-9(8)11/h2-7,14H,1H3,(H,13,15) M03 NAME: 5-hydroxycarbaryl PUBCHEM_CID: NULL INCHI: InChI=1S/C12H11NO3/c1-13-12(15)16-11-7-3-4-8-9(11)5-2-6-10(8)14/h2-7,14H,1H3,(H,13,15) > $$$$ CDK 08101821052D 21 23 0 0 0 0 0 0 0 0999 V2000 -2.9381 7.2156 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2334 4.9635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2200 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2200 -1.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6328 3.4678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9200 1.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9200 -1.7800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5700 -1.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 -1.7800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6353 4.9678 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3325 2.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2700 1.2200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5700 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6200 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6200 -1.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 -1.0300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8689 1.2202 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.9356 5.7156 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 1.2200 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 -1.7800 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 6 3 1 0 0 0 0 7 4 1 0 0 0 0 9 8 2 0 0 0 0 10 5 1 0 0 0 0 11 5 1 0 0 0 0 13 8 1 0 0 0 0 13 12 2 0 0 0 0 14 6 2 0 0 0 0 15 12 1 0 0 0 0 16 7 2 0 0 0 0 16 14 1 0 0 0 0 17 9 1 0 0 0 0 17 15 2 0 0 0 0 18 13 1 0 0 0 0 19 1 1 0 0 0 0 19 2 1 0 0 0 0 19 10 1 0 0 0 0 20 11 1 0 0 0 0 20 14 1 0 0 0 0 20 15 1 0 0 0 0 21 16 1 0 0 0 0 21 17 1 0 0 0 0 M END > InChI=1S/C17H19ClN2S/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)21-17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3 > Chlorpromazine > M01 M02 M03 M04 M05 M06 M07 > M01 M02 M04 M05 M06 M07 > M01 M02 M04 M06 M07 > M02 M04 M07 > M01 NAME: Chlorproazime, N-glucuronide PUBCHEM_CID: Luo H, et al. (1995); N -glucuronidation of aliphatic tertiary amines in human: Antidepressant versus antipsychotic drugs. Xenobiotica 25:291–301. INCHI: InChI=1S/C23H27ClN2O6S/c1-26(2,22-20(29)18(27)19(28)21(32-22)23(30)31)11-5-10-25-14-6-3-4-7-16(14)33-17-9-8-13(24)12-15(17)25/h3-4,6-9,12,18-22,27-29H,5,10-11H2,1-2H3 M02 NAME: PUBCHEM_CID: 1996 ASPET N-Glucuronidation of Xenobiotics Symposium; DRUG METABOLISM AND DISPOSITION; Vol. 26, No. 9 INCHI: InChI=1S/C5H11NO/c1-6(2)4-3-5-7/h5H,3-4H2,1-2H3 M03 NAME: 2-Chlorophenothiazine PUBCHEM_CID: Brunton, L; Chabner, B; Knollman, B (2010). Goodman and Gilman's The Pharmacological Basis of Therapeutics (12th ed.). New York: McGraw-Hill Professional. ISBN 978-0-07-162442-8. INCHI: InChI=1S/C12H8ClNS/c13-8-5-6-12-10(7-8)14-9-3-1-2-4-11(9)15-12/h1-7,14H M04 NAME: Chlorpromazine sulfoxide PUBCHEM_CID: Beckett, AH. et al. (1974); A Polarographie method for the determination of the N-oxide, N-oxide-sulphoxide and sulphoxide metabolites of chlorpromazine; DOI: 10.1111/j.2042-7158.1974.tb09304.x INCHI: InChI=1S/C17H19ClN2OS/c1-19(2)10-5-11-20-14-6-3-4-7-16(14)22(21)17-9-8-13(18)12-15(17)20/h3-4,6-9,12H,5,10-11H2,1-2H3 M05 NAME: 7-Hydroxychlorpromazine PUBCHEM_CID: NULL INCHI: InChI=1S/C17H19ClN2OS/c1-19(2)8-3-9-20-14-6-5-13(21)11-17(14)22-16-7-4-12(18)10-15(16)20/h4-7,10-11,21H,3,8-9H2,1-2H3 M06 NAME: Chlorpromazine N-oxide PUBCHEM_CID: NULL INCHI: InChI=1S/C17H19ClN2OS/c1-20(2,21)11-5-10-19-14-6-3-4-7-16(14)22-17-9-8-13(18)12-15(17)19/h3-4,6-9,12H,5,10-11H2,1-2H3 M07 NAME: Norchlorpromazine PUBCHEM_CID: NULL INCHI: InChI=1S/C16H17ClN2S/c1-18-9-4-10-19-13-5-2-3-6-15(13)20-16-8-7-12(17)11-14(16)19/h2-3,5-8,11,18H,4,9-10H2,1H3 > $$$$ CDK 08101821052D 18 18 0 0 0 0 0 0 0 0999 V2000 7.7951 -1.5010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3040 1.2867 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4962 -0.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3396 0.1378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5989 1.5002 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5989 1.5002 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.5989 -1.5002 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1970 -1.5006 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8624 0.3985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8981 -0.7504 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 2.9341 0.3988 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 6 5 2 0 0 0 0 7 5 1 0 0 0 0 8 6 1 0 0 0 0 9 7 2 0 0 0 0 10 6 1 0 0 0 0 11 7 1 0 0 0 0 12 8 1 0 0 0 0 13 8 2 0 0 0 0 13 9 1 0 0 0 0 14 3 1 0 0 0 0 15 4 1 0 0 0 0 16 9 1 0 0 0 0 17 14 1 0 0 0 0 17 15 1 0 0 0 0 17 16 1 0 0 0 0 18 17 2 0 0 0 0 M END > InChI=1S/C9H11Cl3NO3PS/c1-3-14-17(18,15-4-2)16-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3 > Chlorpyrifos > M01 M02 M03 M04 M05 > M02 M03 M04 M05 > > > M01 NAME: 2-Amino-5-((1-((carboxymethyl)amino)-3-(ethylthio)-1-oxopropan-2-yl)amino)-5-oxopentanoic acid PUBCHEM_CID: NULL INCHI: InChI=1S/C12H21N3O6S/c1-2-22-6-8(11(19)14-5-10(17)18)15-9(16)4-3-7(13)12(20)21/h7-8H,2-6,13H2,1H3,(H,14,19)(H,15,16)(H,17,18)(H,20,21) M02 NAME: Ethoxy-hydroxy-sulfanylidene-(3,5,6-trichloropyridin-2-yl)oxy-phosphorane PUBCHEM_CID: 181829 INCHI: InChI=1S/C7H7Cl3NO3PS/c1-2-13-15(12,16)14-7-5(9)3-4(8)6(10)11-7/h3H,2H2,1H3,(H,12,16) M03 NAME: Chlorpyrifos oxon PUBCHEM_CID: 21804 INCHI: InChI=1S/C9H11Cl3NO4P/c1-3-15-18(14,16-4-2)17-9-7(11)5-6(10)8(12)13-9/h5H,3-4H2,1-2H3 M04 NAME: NSC289403 PUBCHEM_CID: 17173 INCHI: InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9) M05 NAME: 2-Hydroxy-3,5,6-trichloropyridine PUBCHEM_CID: 23017 INCHI: InChI=1S/C5H2Cl3NO/c6-2-1-3(7)5(10)9-4(2)8/h1H,(H,9,10) > METABOLISM OF CHLORPYRIFOS BY HUMAN CYTOCHROME P450 ISOFORMS AND HUMAN, MOUSE, AND RAT LIVER MICROSOMES Fujioka, K. and Casida, JE. (2007); Glutathione S-Transferase Conjugation of Organophosphorus Pesticides Yields S-Phospho-, S-Aryl-, and S-Alkylglutathione Derivatives; Chem. Res. Toxicol. 2007, 20, 1211–1217 $$$$ CDK 08101821052D 14 14 0 0 0 0 0 0 0 0999 V2000 -3.8952 -1.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5958 0.7513 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1998 -2.2463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5962 -2.2487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2968 0.0011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5960 0.7437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8950 -0.0063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3015 0.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -2.2493 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8996 -1.4985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3010 -1.4993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0018 -2.2491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2971 -1.4989 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0016 -3.7491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 1 1 0 0 0 0 5 2 1 0 0 0 0 7 6 2 0 0 0 0 8 6 1 0 0 0 0 10 3 1 0 0 0 0 10 7 1 0 0 0 0 10 9 2 0 0 0 0 11 8 2 0 0 0 0 11 9 1 0 0 0 0 12 11 1 0 0 0 0 13 4 1 0 0 0 0 13 5 1 0 0 0 0 13 12 1 0 0 0 0 14 12 2 0 0 0 0 M END > InChI=1S/C12H17NO/c1-4-13(5-2)12(14)11-8-6-7-10(3)9-11/h6-9H,4-5H2,1-3H3 > DEET > M01 M02 M03 > M01 M02 M03 > M03 > M03 > M01 NAME: N-ethyl-m-toluamide PUBCHEM_CID: 93103 INCHI: InChI=1S/C10H13NO/c1-3-11-10(12)9-6-4-5-8(2)7-9/h4-7H,3H2,1-2H3,(H,11,12) M02 NAME: acetaldehyde PUBCHEM_CID: 177 INCHI: InChI=1S/C2H4O/c1-2-3/h2H,1H3 M03 NAME: N,N-diethyl-3-hydroxymethylbenzamide PUBCHEM_CID: 155712 INCHI: InChI=1S/C12H17NO2/c1-3-13(4-2)12(15)11-7-5-6-10(8-11)9-14/h5-8,14H,3-4,9H2,1-2H3 > Usmani, KA et al. (2002); In Vitro Human Metabolism and Interactions of Repellent N,N-Diethyl-m-Toluamide; Drug Metab Dispos.;30(3):289-94; PMID:11854147 $$$$ CDK 08101821052D 23 25 0 0 1 0 0 0 0 0999 V2000 9.9141 -2.3190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7475 4.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2377 -1.3025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2673 -2.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6161 -1.5672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3161 -2.3154 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0181 -1.5636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7180 -2.3118 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0600 2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0600 0.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4500 2.1900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4200 -0.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1300 -2.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7500 2.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4200 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 0.7000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7600 -0.0500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1300 0.7000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8300 -0.0500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7600 -1.5600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1325 2.2000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4600 -2.3000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 1 1 0 0 0 0 6 5 1 0 0 0 0 7 6 1 0 0 0 0 8 7 1 0 0 0 0 10 9 1 0 0 0 0 14 2 1 0 0 0 0 14 9 1 0 0 0 0 14 11 2 0 0 0 0 15 8 1 0 0 0 0 15 12 2 0 0 0 0 15 13 1 0 0 0 0 16 11 1 0 0 0 0 17 10 1 0 0 0 0 17 16 1 0 0 0 0 18 12 1 0 0 0 0 19 13 2 0 0 0 0 20 16 1 0 0 0 0 20 18 2 0 0 0 0 20 19 1 0 0 0 0 21 3 1 0 0 0 0 21 4 1 0 0 0 0 21 17 1 0 0 0 0 22 18 1 0 0 0 0 23 19 1 0 0 0 0 23 21 1 0 0 0 0 M END > InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1 > Delta-9-Tetrahydrocannabinol > M01 M02 M03 M04 M05 M06 M07 M08 M09 > M01 M02 M03 M04 M05 M06 M07 M08 M09 > M03 M05 M06 > > M01 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C27H38O8/c1-5-6-7-8-15-12-18(33-26-23(30)21(28)22(29)24(34-26)25(31)32)20-16-11-14(2)9-10-17(16)27(3,4)35-19(20)13-15/h11-13,16-17,21-24,26,28-30H,5-10H2,1-4H3,(H,31,32) M02 NAME: 3'-Hydroxytetrahydrocannabinol-delta(9) PUBCHEM_CID: 194062 INCHI: InChI=1S/C21H30O3/c1-5-15(22)8-7-14-11-18(23)20-16-10-13(2)6-9-17(16)21(3,4)24-19(20)12-14/h10-12,15-17,22-23H,5-9H2,1-4H3 M03 NAME: 11-Hydroxy-delta(9)-thc PUBCHEM_CID: 37482 INCHI: InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3 M04 NAME: 8.alpha.-Hydroxy-.delta.-9-tetrahydrocannabinol PUBCHEM_CID: 623131 INCHI: InChI=1S/C21H30O3/c1-5-6-7-8-14-10-18(23)20-15-9-13(2)17(22)12-16(15)21(3,4)24-19(20)11-14/h9-11,15-17,22-23H,5-8,12H2,1-4H3 M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-5-6-7-17(22)14-11-18(23)20-15-10-13(2)8-9-16(15)21(3,4)24-19(20)12-14/h10-12,15-17,22-23H,5-9H2,1-4H3 M06 NAME: 4'-Hydroxy-thc PUBCHEM_CID: 6453619 INCHI: InChI=1S/C21H30O3/c1-13-8-9-17-16(10-13)20-18(23)11-15(7-5-6-14(2)22)12-19(20)24-21(17,3)4/h10-12,14,16-17,22-23H,5-9H2,1-4H3 M07 NAME: 1alpha,2alpha-Epoxyhexahydrocannabinol (9,10-Epoxy-delta-9-tetrahydrocannabinol) PUBCHEM_CID: 125763 INCHI: InChI=1S/C21H30O3/c1-5-6-7-8-13-11-15(22)18-16(12-13)23-20(2,3)14-9-10-21(4)19(24-21)17(14)18/h11-12,14,17,19,22H,5-10H2,1-4H3 M08 NAME: 9-alpha,10-alpha-epoxyhexahydrocannabinol PUBCHEM_CID: 125763 INCHI: InChI=1S/C21H30O3/c1-14-8-9-17-16(11-14)20-18(23)12-15(7-5-4-6-10-22)13-19(20)24-21(17,2)3/h11-13,16-17,22-23H,4-10H2,1-3H3 M09 NAME: 3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo[b,d]pyran-1,7-diol PUBCHEM_CID: 101929786 INCHI: InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-15-9-13(2)10-17(23)20(15)21(3,4)24-18(19)12-14/h9,11-12,15,17,20,22-23H,5-8,10H2,1-4H3 > Schwilke, EW. et al. (2009); Δ9-Tetrahydrocannabinol (THC), 11-Hydroxy-THC, and 11-Nor-9-carboxy-THC Plasma Pharmacokinetics during and after Continuous High-Dose Oral THC; Clin Chem. 2009 Dec; 55(12): 2180–2189; doi: 10.1373/clinchem.2008.122119; PMCID: PMC3196989 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 Ricardo Jorge Dinis-Oliveira (2016); Metabolomics of Δ9-tetrahydrocannabinol: implications in toxicity; Drug metabolism reviews [0360-2532] yr:2016 vol:48 iss:1 pg:80-87; http://dx.doi.org/10.3109/03602532.2015.1137307 $$$$ CDK 08101821052D 14 13 0 0 0 0 0 0 0 0999 V2000 11.6913 -2.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1998 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 -2.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2356 -1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -2.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 -2.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0377 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0933 -2.7877 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7584 -0.8886 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -2.0377 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 6.8300 -0.8886 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.0377 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -2.7877 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4 1 1 0 0 0 0 5 2 1 0 0 0 0 6 3 1 0 0 0 0 8 7 1 0 0 0 0 9 4 1 0 0 0 0 10 5 1 0 0 0 0 11 9 1 0 0 0 0 11 10 1 0 0 0 0 12 11 2 0 0 0 0 13 6 1 0 0 0 0 13 7 1 0 0 0 0 14 8 1 0 0 0 0 14 11 1 0 0 0 0 M END > InChI=1S/C8H19O2PS3/c1-4-9-11(12,10-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 > Disulfoton > M01 M02 > M01 M02 > M01 M02 > M02 > M01 NAME: Demeton-S PUBCHEM_CID: 24723 INCHI: InChI=1S/C8H19O3PS2/c1-4-10-12(9,11-5-2)14-8-7-13-6-3/h4-8H2,1-3H3 M02 NAME: Disulfoton-sulfoxide PUBCHEM_CID: 17242 INCHI: InChI=1S/C8H19O3PS3/c1-4-10-12(13,11-5-2)14-7-8-15(9)6-3/h4-8H2,1-3H3 > $$$$ CDK 08101821052D 14 14 0 0 0 0 0 0 0 0999 V2000 -4.7899 4.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5399 5.5669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0408 0.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2908 -0.9288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2109 1.6703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2899 1.6698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2101 -0.9283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9609 0.3712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5399 2.9688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9601 -2.2273 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4609 0.3710 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.0399 2.9688 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 4.2679 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2899 1.6698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 6 3 1 0 0 0 0 6 5 2 0 0 0 0 7 4 1 0 0 0 0 8 5 1 0 0 0 0 8 7 2 0 0 0 0 10 7 1 0 0 0 0 11 8 1 0 0 0 0 12 6 1 0 0 0 0 12 9 2 0 0 0 0 13 1 1 0 0 0 0 13 2 1 0 0 0 0 13 9 1 0 0 0 0 14 9 1 4 0 0 0 M END > InChI=1S/C9H10Cl2N2O/c1-13(2)9(14)12-6-3-4-7(10)8(11)5-6/h3-5H,1-2H3,(H,12,14) > Diuron > M01 M02 > M01 > M01 > M01 > M01 NAME: N-Demethoxylinuron PUBCHEM_CID: 19113 INCHI: InChI=1S/C8H8Cl2N2O/c1-11-8(13)12-5-2-3-6(9)7(10)4-5/h2-4H,1H3,(H2,11,12,13) M02 NAME: Urea, N'-(3,4-dichlorophenyl)-N-(hydroxymethyl)-N-methyl- PUBCHEM_CID: 14299444 INCHI: InChI=1S/C9H10Cl2N2O2/c1-13(5-14)9(15)12-6-2-3-7(10)8(11)4-6/h2-4,14H,5H2,1H3,(H,12,15) > Abass, K. et. al. (2007); Characterization of Diuron N-Demethylation by Mammalian Hepatic Microsomes and cDNA-Expressed Human Cytochrome P450 Enzymes; Drug Metab Dispos.; 35(9):1634-41; PMID:17576805; DOI:10.1124/dmd.107.016295 Ohkawa, H. and Inui, H. (2014); Metabolism of agrochemicals and related environmental chemicals based on cytochrome P450s in mammals and plants; Pest Manag Sci 2015; 71: 824–828; DOI 10.1002/ps.3871 $$$$ CDK 08101821052D 28 31 0 0 0 0 0 0 0 0999 V2000 -4.9081 0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 -0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8500 6.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8500 3.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3500 6.4962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3500 3.8962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3508 1.2986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0992 2.5986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1008 2.5976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8492 3.8976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6000 5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 -1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3500 3.8971 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1853 -2.6360 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 5 3 1 0 0 0 0 6 4 1 0 0 0 0 7 5 2 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 17 8 1 0 0 0 0 17 9 1 0 0 0 0 17 12 1 0 0 0 0 18 6 2 0 0 0 0 18 7 1 0 0 0 0 18 16 1 0 0 0 0 19 13 1 0 0 0 0 19 14 2 0 0 0 0 20 12 1 0 0 0 0 20 13 1 0 0 0 0 21 15 2 0 0 0 0 21 19 1 0 0 0 0 22 14 1 0 0 0 0 23 15 1 0 0 0 0 23 22 2 0 0 0 0 24 20 1 0 0 0 0 24 21 1 0 0 0 0 25 10 1 0 0 0 0 25 11 1 0 0 0 0 25 16 1 0 0 0 0 26 24 2 0 0 0 0 27 1 1 0 0 0 0 27 22 1 0 0 0 0 28 2 1 0 0 0 0 28 23 1 0 0 0 0 M END > InChI=1/C24H29NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20H,8-13,16H2,1-2H3 > Donepezil > M01 M02 M03 M04 M05 M06 > M01 M02 M03 M04 M05 M06 > M01 M02 M03 M05 M06 > M01 M02 M05 M06 > M01 NAME: 5,6-Dimethoxy-2-(piperidin-4-ylmethyl)-2,3-dihydro-1H-inden-1-one PUBCHEM_CID: 10446897 INCHI: InChI=1S/C17H23NO3/c1-20-15-9-12-8-13(7-11-3-5-18-6-4-11)17(19)14(12)10-16(15)21-2/h9-11,13,18H,3-8H2,1-2H3 M02 NAME: benzaldehyde PUBCHEM_CID: 240 INCHI: InChI=1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H29NO4/c1-28-22-13-18-12-19(24(27)21(18)14-23(22)29-2)11-16-7-9-25(10-8-16)15-17-3-5-20(26)6-4-17/h3-6,13-14,16,19,26H,7-12,15H2,1-2H3 M04 NAME: Donepezil N-Oxide PUBCHEM_CID: 11188628 INCHI: InChI=1S/C24H29NO4/c1-28-22-14-19-13-20(24(26)21(19)15-23(22)29-2)12-17-8-10-25(27,11-9-17)16-18-6-4-3-5-7-18/h3-7,14-15,17,20H,8-13,16H2,1-2H3 M05 NAME: 6-O-Desmethyl Donepezil PUBCHEM_CID: 14553555 INCHI: InChI=1S/C23H27NO3/c1-27-22-13-18-12-19(23(26)20(18)14-21(22)25)11-16-7-9-24(10-8-16)15-17-5-3-2-4-6-17/h2-6,13-14,16,19,25H,7-12,15H2,1H3 M06 NAME: 5-O-Desmethyl Donepezil PUBCHEM_CID: 11503234 INCHI: InChI=1S/C23H27NO3/c1-27-22-14-20-18(13-21(22)25)12-19(23(20)26)11-16-7-9-24(10-8-16)15-17-5-3-2-4-6-17/h2-6,13-14,16,19,25H,7-12,15H2,1H3 > (Chapter 23 - Substrates of Human CYP2D6; p178) Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 21 23 0 0 1 0 0 0 0 0999 V2000 -1.8531 -6.4255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0023 -5.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6281 -3.7983 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3359 -2.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5922 -4.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2641 -2.6492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8989 -1.5002 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.7413 -2.3889 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 0.9649 -3.3990 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 2.7769 -4.0588 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 4 3 2 0 0 0 0 6 5 3 0 0 0 0 8 1 1 0 0 0 0 8 2 1 0 0 0 0 8 5 1 0 0 0 0 9 3 1 0 0 0 0 9 7 2 0 0 0 0 10 7 1 0 0 0 0 11 4 1 0 0 0 0 11 10 2 0 0 0 0 13 6 1 1 0 0 0 13 10 1 6 0 0 0 14 13 1 0 0 0 0 15 9 1 0 0 0 0 16 14 1 0 0 0 0 17 14 1 0 0 0 0 18 14 1 0 0 0 0 19 11 1 0 0 0 0 19 12 2 0 0 0 0 20 12 1 0 0 0 0 21 12 1 0 0 0 0 21 13 1 0 0 0 0 M END > InChI=1S/C14H9ClF3NO2/c15-9-3-4-11-10(7-9)13(14(16,17)18,21-12(20)19-11)6-5-8-1-2-8/h3-4,7-8H,1-2H2,(H,19,20)/t13-/m0/s1 > Efavirenz > M01 M02 > M01 M02 M03 > > > M01 NAME: 7-Hydroxyefavirenz PUBCHEM_CID: 40621976 INCHI: InChI=1S/C14H9ClF3NO3/c15-9-5-8-10(6-11(9)20)19-12(21)22-13(8,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1 M02 NAME: 8-Hydroxyefavirenz PUBCHEM_CID: 487643 INCHI: InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1 M03 NAME: Efivavirenz, N-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C20H17ClF3NO8/c21-9-3-4-11-10(7-9)19(20(22,23)24,6-5-8-1-2-8)33-18(31)25(11)16-14(28)12(26)13(27)15(32-16)17(29)30/h3-4,7-8,12-16,26-28H,1-2H2,(H,29,30)/t12?,13?,14?,15?,16?,19-/m0/s1 > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 Bumpus, NN. et al. (2006); Metabolism of Efavirenz and 8-Hydroxyefavirenz by P450 2B6 Leads to Inactivation by Two Distinct Mechanisms; J Pharmacol Exp Ther. 2006 Jul;318(1):345-51; PMID:16611850 DOI: 0.1124/jpet.106.102525 $$$$ CDK 08101821052D 22 24 0 0 0 0 0 0 0 0999 V2000 -12.8117 -2.5966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3100 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4300 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4300 -1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5610 -3.8963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5615 -1.2977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0602 -3.8970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0606 -1.2984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4300 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4300 -1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3117 -2.5966 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3100 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5600 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8100 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0600 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8100 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0705 -4.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4005 -3.1111 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8100 -2.5981 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 2 1 0 0 0 0 4 2 1 0 0 0 0 7 5 1 0 0 0 0 8 6 2 0 0 0 0 11 1 1 0 0 0 0 11 5 2 0 0 0 0 11 6 1 0 0 0 0 12 3 1 0 0 0 0 12 9 1 0 0 0 0 13 4 1 0 0 0 0 13 10 1 0 0 0 0 13 12 1 0 0 0 0 14 7 2 0 0 0 0 14 8 1 0 0 0 0 16 15 2 0 0 0 0 17 15 1 0 0 0 0 18 9 1 0 0 0 0 18 10 1 0 0 0 0 18 16 1 0 0 0 0 19 15 1 4 0 0 0 22 14 1 0 0 0 0 22 17 1 0 0 0 0 22 20 2 0 0 0 0 22 21 2 0 0 0 0 M END > InChI=1/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19) > Gliclazide > M01 M02 M03 > M01 M02 M03 > M01 > > M01 NAME: Methylhydroxygliclazide PUBCHEM_CID: 192219 INCHI: InChI=1S/C15H21N3O4S/c19-10-11-4-6-14(7-5-11)23(21,22)17-15(20)16-18-8-12-2-1-3-13(12)9-18/h4-7,12-13,19H,1-3,8-10H2,(H2,16,17,20) M02 NAME: 6-Hydroxygliclazide PUBCHEM_CID: 75051323 INCHI: InChI=1S/C15H21N3O4S/c1-10-2-5-12(6-3-10)23(21,22)17-15(20)16-18-8-11-4-7-14(19)13(11)9-18/h2-3,5-6,11,13-14,19H,4,7-9H2,1H3,(H2,16,17,20) M03 NAME: 7-Hydroxygliclazide PUBCHEM_CID: 131750725 INCHI: InChI=1S/C15H21N3O4S/c1-10-2-4-14(5-3-10)23(21,22)17-15(20)16-18-8-11-6-13(19)7-12(11)9-18/h2-5,11-13,19H,6-9H2,1H3,(H2,16,17,20) > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 14 14 0 0 0 0 0 0 0 0999 V2000 6.1826 -0.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3359 -2.6012 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2839 1.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1413 -2.8616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8826 0.2773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2837 0.2775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1826 -1.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -3.7504 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.9850 2.5277 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.1054 -1.7124 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5826 -0.4727 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.0699 -3.3824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8826 -2.7227 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5826 -1.9727 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 4 2 1 0 0 0 0 5 1 1 0 0 0 0 6 3 1 0 0 0 0 7 1 1 0 0 0 0 8 2 1 0 0 0 0 9 3 1 0 0 0 0 10 4 1 0 0 0 0 11 5 1 0 0 0 0 11 6 1 0 0 0 0 13 7 1 0 0 0 0 14 10 1 0 0 0 0 14 11 1 0 0 0 0 14 12 2 0 0 0 0 14 13 1 0 0 0 0 M END > InChI=1/C7H15Cl2N2O2P/c8-2-4-10-14(12)11(6-3-9)5-1-7-13-14/h1-7H2,(H,10,12) > Ifosfamide > M01 M02 M03 M04 > M02 M03 M04 > M02 M03 M04 > > M01 NAME: 4-Hydroxyifosfamide PUBCHEM_CID: 308171 INCHI: InChI=1S/C7H15Cl2N2O3P/c8-2-4-10-15(13)11(5-3-9)7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13) M02 NAME: Dechloroethylcyclophosphamide PUBCHEM_CID: 114861 INCHI: InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9) M03 NAME: 2-chloroacetaldehyde PUBCHEM_CID: 33 INCHI: InChI=1S/C2H3ClO/c3-1-2-4/h2H,1H2 M04 NAME: 2-Dechloroethylifosfamide PUBCHEM_CID: 119105 INCHI: InChI=1S/C5H12ClN2O2P/c6-2-4-8-3-1-5-10-11(8,7)9/h1-5H2,(H2,7,9) > $$$$ CDK 08101821052D 17 18 0 0 0 0 0 0 0 0999 V2000 -0.5282 3.7919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0207 3.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4328 -1.5148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4330 -0.4064 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8006 1.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5735 2.2632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0818 2.4207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9031 2.7372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6428 0.5810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3948 2.8946 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.8086 -0.9119 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2930 1.3659 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.7550 1.5875 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1830 0.8926 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.1827 1.1275 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.2950 2.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4983 -0.3390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 4 3 1 0 0 0 0 7 1 1 0 0 0 0 7 5 2 0 0 0 0 7 6 1 0 0 0 0 8 2 1 0 0 0 0 10 8 1 0 0 0 0 11 3 1 0 0 0 0 11 9 2 0 0 0 0 12 5 1 0 0 0 0 12 8 2 0 0 0 0 13 9 1 0 0 0 0 14 4 1 0 0 0 0 14 6 1 0 0 0 0 14 9 1 0 0 0 0 15 13 1 0 0 0 0 16 15 2 0 0 0 0 17 15 2 0 0 0 0 M END > InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13) > Imidacloprid > M01 M02 M03 > M04 M05 > > > M01 NAME: 5-HYDROXYIMIDACLOPRID PUBCHEM_CID: 19417551 INCHI: InChI=1S/C9H10ClN5O3/c10-7-2-1-6(3-11-7)5-14-8(16)4-12-9(14)13-15(17)18/h1-3,8,16H,4-5H2,(H,12,13) M02 NAME: 4-HYDROXYIMIDACLOPRID PUBCHEM_CID: NULL INCHI: InChI=1S/C9H10ClN5O3/c10-7-2-1-6(3-11-7)4-14-5-8(16)12-9(14)13-15(17)18/h1-3,8,16H,4-5H2,(H,12,13) M03 NAME: 1H-Imidazol-2-amine, 1-((6-chloro-3-pyridinyl)methyl)-4,5-dihydro-N-nitroso- PUBCHEM_CID: NULL INCHI: InChI=1S/C9H10ClN5O/c10-8-2-1-7(5-12-8)6-15-4-3-11-9(15)13-14-16/h1-2,5H,3-4,6H2,(H,11,13,16) M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C3H6N4O2/c8-7(9)6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6) M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C6H4ClNO/c7-6-2-1-5(4-9)3-8-6/h1-4H > http://www.inchem.org/documents/jmpr/jmpmono/2001pr07.htm#2.1.2 $$$$ CDK 08101821052D 31 33 0 0 0 0 0 0 0 0999 V2000 7.4140 -2.1468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2632 -0.1598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4794 -3.1429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4817 -1.6429 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1783 -3.8909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9801 -3.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6855 -3.1346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1828 -0.8909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8794 -3.1389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2791 -3.1267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9841 -0.8837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2672 -4.4326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6143 0.6161 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6851 -1.6337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8817 -1.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2836 -1.6346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2629 -2.9326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6141 -0.8839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5683 -5.1789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5111 -1.6346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2122 -0.8844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0033 -1.6371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5726 -6.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8652 -4.4251 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.8738 -7.4251 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 5.0947 -6.4226 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 6.0637 -8.0899 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 0.6146 2.1161 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2124 0.6156 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5839 -0.8867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9130 -1.6342 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 5 3 1 0 0 0 0 7 6 2 0 0 0 0 8 4 1 0 0 0 0 9 5 2 0 0 0 0 10 6 1 0 0 0 0 14 7 1 0 0 0 0 14 11 2 0 0 0 0 15 8 2 0 0 0 0 15 9 1 0 0 0 0 16 10 2 0 0 0 0 16 11 1 0 0 0 0 17 12 1 0 0 0 0 18 13 1 0 0 0 0 18 14 1 0 0 0 0 12 19 2 0 0 0 0 20 17 1 0 0 0 0 21 20 1 0 0 0 0 22 1 1 0 0 0 0 22 2 1 0 0 0 0 22 17 1 0 0 0 0 22 20 1 0 0 0 0 23 19 1 0 0 0 0 24 19 1 0 0 0 0 25 23 1 0 0 0 0 26 23 1 0 0 0 0 27 23 1 0 0 0 0 28 13 3 0 0 0 0 29 21 2 0 0 0 0 30 15 1 0 0 0 0 30 16 1 0 0 0 0 31 18 1 0 0 0 0 31 21 1 0 0 0 0 M END > InChI=1/C23H19ClF3NO3/c1-22(2)17(12-19(24)23(25,26)27)20(22)21(29)31-18(13-28)14-7-6-10-16(11-14)30-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/b19-12- > Lambda-cyhalothrin > M01 M02 > M01 M02 > M01 M02 > > M01 NAME: 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid PUBCHEM_CID: 6440522 INCHI: InChI=1S/C9H10ClF3O2/c1-8(2)4(6(8)7(14)15)3-5(10)9(11,12)13/h3-4,6H,1-2H3,(H,14,15)/b5-3- M02 NAME: 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile 3-Phenoxybenzaldehyde cyanohydrin PUBCHEM_CID: NULL INCHI: InChI=1S/C14H11NO2/c15-10-14(16)11-5-4-8-13(9-11)17-12-6-2-1-3-7-12/h1-9,14,16H > http://www.inchem.org/documents/ehc/ehc/ehc99.htm $$$$ CDK 08101821052D 17 17 0 0 0 0 0 0 0 0999 V2000 -1.8800 -0.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5813 -2.6688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6153 -2.6700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2142 1.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5808 0.3312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7178 -1.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5142 -1.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2142 -2.6698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5142 -0.4198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0172 0.3308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9142 -1.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2142 0.3302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3162 -0.4194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9142 -0.4198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6153 0.3304 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -0.4190 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3159 -1.9194 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 1 1 0 0 0 0 6 2 1 0 0 0 0 8 7 2 0 0 0 0 9 7 1 0 0 0 0 11 3 1 0 0 0 0 11 8 1 0 0 0 0 12 4 1 0 0 0 0 12 9 2 0 0 0 0 13 10 1 0 0 0 0 14 11 2 0 0 0 0 14 12 1 0 0 0 0 15 13 2 0 0 0 0 15 14 1 0 0 0 0 16 5 1 0 0 0 0 16 6 1 0 0 0 0 16 10 1 0 0 0 0 17 13 1 4 0 0 0 M END > InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17) > Lidocaine > M01 M02 M03 M04 M05 > M02 M03 M04 M05 M06 M07 > M04 M05 M06 M07 > > M01 NAME: 3-Hydroxylidocaine PUBCHEM_CID: 161824 INCHI: InChI=1S/C14H22N2O2/c1-5-16(6-2)9-13(18)15-14-10(3)7-8-12(17)11(14)4/h7-8,17H,5-6,9H2,1-4H3,(H,15,18) M02 NAME: Lidocaine N-oxide PUBCHEM_CID: 3036923 INCHI: InChI=1S/C14H22N2O2/c1-5-16(18,6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17) M03 NAME: Acetamide, 2-(diethylamino)-N-(4-hydroxy-2,6-dimethylphenyl)- 4-Hydroxylidocaine (OR 4-Hydroxylidocaine) PUBCHEM_CID: 13932575 INCHI: InChI=1S/C14H22N2O2/c1-5-16(6-2)9-13(18)15-14-10(3)7-12(17)8-11(14)4/h7-8,17H,5-6,9H2,1-4H3,(H,15,18) M04 NAME: Monoethylglycinexylidide PUBCHEM_CID: 24415 INCHI: InChI=1S/C12H18N2O/c1-4-13-8-11(15)14-12-9(2)6-5-7-10(12)3/h5-7,13H,4,8H2,1-3H3,(H,14,15) M05 NAME: acetaldehyde PUBCHEM_CID: 177 INCHI: InChI=1S/C2H4O/c1-2-3/h2H,1H3 M06 NAME: 2,6-Dimethylaniline PUBCHEM_CID: NULL INCHI: InChI=1S/C8H11N/c1-6-4-3-5-7(2)8(6)9/h3-5H,9H2,1-2H3 M07 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C6H13NO2/c1-3-7(4-2)5-6(8)9/h3-5H2,1-2H3,(H,8,9) > Wang, B. and Zhou, S.-F. (2009); Synthetic and Natural Compounds that Interact with Human Cytochrome P450 1A2 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 4066-4218 $$$$ CDK 08101821052D 20 19 0 0 0 0 0 0 0 0999 V2000 7.4695 -1.6875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7685 -0.9375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7685 0.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0675 1.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0675 2.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3666 3.5625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3666 5.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0675 5.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0675 7.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7685 8.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4695 7.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1704 8.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8714 7.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5724 8.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2733 7.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9743 8.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3248 7.3125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6238 8.0625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6238 9.5625 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9228 7.3125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 3 2 1 0 0 0 0 4 3 1 0 0 0 0 5 4 1 0 0 0 0 6 5 1 0 0 0 0 6 7 2 0 0 0 0 8 7 1 0 0 0 0 9 8 1 0 0 0 0 9 10 2 0 0 0 0 11 10 1 0 0 0 0 12 11 1 0 0 0 0 13 12 1 0 0 0 0 14 13 1 0 0 0 0 15 14 1 0 0 0 0 16 15 1 0 0 0 0 17 16 1 0 0 0 0 18 17 1 0 0 0 0 19 18 2 0 0 0 0 20 18 1 0 0 0 0 M END > InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- > Linoleic acid > M01 M02 M03 M04 M05 M06 M07 M08 M09 M10 M11 > M03 M04 M08 M09 M10 M11 > M03 M04 M08 M09 M10 M11 > > M01 NAME: 1-(9Z,12Z)-octadecadienoylglycerone 3-phosphate PUBCHEM_CID: 86289258 INCHI: InChI=1S/C21H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h6-7,9-10H,2-5,8,11-19H2,1H3,(H2,24,25,26)/p-2/b7-6-,10-9- M02 NAME: lineoyl-CoA PUBCHEM_CID: NULL INCHI: InChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11- M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O8/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(25)31-24-21(28)19(26)20(27)22(32-24)23(29)30/h6-7,9-10,19-22,24,26-28H,2-5,8,11-17H2,1H3,(H,29,30)/b7-6-,10-9- M04 NAME: 8-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-2-3-4-5-6-7-8-11-14-17(19)15-12-9-10-13-16-18(20)21/h6-7,11,14,17,19H,2-5,8-10,12-13,15-16H2,1H3,(H,20,21)/b7-6-,14-11- M05 NAME: 11-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-2-3-4-8-11-14-17(19)15-12-9-6-5-7-10-13-16-18(20)21/h11-12,14-15,17,19H,2-10,13,16H2,1H3,(H,20,21)/b14-11-,15-12- M06 NAME: 13-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-2-3-11-14-17(19)15-12-9-7-5-4-6-8-10-13-16-18(20)21/h7,9,12,15,17,19H,2-6,8,10-11,13-14,16H2,1H3,(H,20,21)/b9-7-,15-12+ M07 NAME: 9-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-2-3-4-5-6-8-11-14-17(19)15-12-9-7-10-13-16-18(20)21/h6,8,11,14,17,19H,2-5,7,9-10,12-13,15-16H2,1H3,(H,20,21)/b8-6-,14-11? M08 NAME: 17-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h2-3,7,9,17,19H,4-6,8,10-16H2,1H3,(H,20,21)/b3-2-,9-7- M09 NAME: Leukotoxin PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9- M10 NAME: Isoleukotoxin PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8- M11 NAME: 18-HODE PUBCHEM_CID: NULL INCHI: InChI=1S/C18H32O3/c19-17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18(20)21/h1-2,5,7,19H,3-4,6,8-17H2,(H,20,21)/b2-1-,7-5- > Turgeon D et al. (2003); Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases; J Lipid Res. 2003 Jun;44(6):1182-91. Epub 2003 Mar 16 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 23 25 0 0 0 0 0 0 0 0999 V2000 5.1983 -0.7496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0948 3.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7952 3.7517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0956 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4963 3.0015 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7966 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4970 1.5006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8989 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1981 0.7504 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8987 3.0002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8989 -1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 5 3 1 0 0 0 0 7 6 2 0 0 0 0 8 4 1 0 0 0 0 9 5 2 0 0 0 0 10 6 1 0 0 0 0 11 7 1 0 0 0 0 12 8 2 0 0 0 0 12 9 1 0 0 0 0 13 10 2 0 0 0 0 14 11 2 0 0 0 0 14 13 1 0 0 0 0 16 13 1 0 0 0 0 16 15 2 0 0 0 0 17 15 1 0 0 0 0 18 15 1 0 0 0 0 19 1 1 0 0 0 0 19 12 1 0 0 0 0 19 17 1 0 0 0 0 20 2 1 0 0 0 0 20 14 1 0 0 0 0 20 18 1 0 0 0 0 21 16 1 0 0 0 0 22 17 2 0 0 0 0 23 18 2 0 0 0 0 M END > InChI=1S/C18H16N2O3/c1-19(12-8-4-3-5-9-12)17(22)15-16(21)13-10-6-7-11-14(13)20(2)18(15)23/h3-11,21H,1-2H3 > Linomide > M01 M02 M03 M04 M05 M06 M07 > M02 M04 M05 M06 M07 > M04 M06 M07 > > M01 NAME: linomide O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C24H24N2O9/c1-25(12-8-4-3-5-9-12)21(30)15-19(13-10-6-7-11-14(13)26(2)22(15)31)34-24-18(29)16(27)17(28)20(35-24)23(32)33/h3-11,16-18,20,24,27-29H,1-2H3,(H,32,33) M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C18H16N2O4/c1-19(11-6-4-3-5-7-11)17(23)15-16(22)13-9-8-12(21)10-14(13)20(2)18(15)24/h3-10,21-22H,1-2H3 M03 NAME: PUBCHEM_CID: 54717876 INCHI: InChI=1S/C18H16N2O4/c1-19(11-6-4-3-5-7-11)17(23)15-16(22)13-10-12(21)8-9-14(13)20(2)18(15)24/h3-10,21-22H,1-2H3 M04 NAME: PUBCHEM_CID: 54717849 INCHI: InChI=1S/C18H16N2O4/c1-19(11-7-9-12(21)10-8-11)17(23)15-16(22)13-5-3-4-6-14(13)20(2)18(15)24/h3-10,21-22H,1-2H3 M05 NAME: PUBCHEM_CID: 121391236 INCHI: InChI=1S/C18H16N2O4/c1-19(11-7-4-3-5-8-11)17(23)14-16(22)12-9-6-10-13(21)15(12)20(2)18(14)24/h3-10,21-22H,1-2H3 M06 NAME: 2-hydroxy-1-methyl-4-oxo-N-phenylquinoline-3-carboxamide PUBCHEM_CID: 54676449 INCHI: InChI=1S/C17H14N2O3/c1-19-13-10-6-5-9-12(13)15(20)14(17(19)22)16(21)18-11-7-3-2-4-8-11/h2-10,20H,1H3,(H,18,21) M07 NAME: N-methyl-N-phenyl-1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxamide PUBCHEM_CID: 54682853 INCHI: InChI=1S/C17H14N2O3/c1-19(11-7-3-2-4-8-11)17(22)14-15(20)12-9-5-6-10-13(12)18-16(14)21/h2-10H,1H3,(H2,18,20,21) > Dorwald, FZ. (2013); Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds; ISBN: 978-3-527-64565-7; p. 461 Tuvesson,H. et al.(2000) Identification of cytochrome P4503A as the major subfamily responsible for the metabolismof roquinimex in man, Xenobiotica, 30:9, 905-914, DOI: 10.1080/004982500433327 $$$$ CDK 08101821052D 20 20 0 0 0 0 0 0 0 0999 V2000 3.3162 -5.6706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9151 -1.1704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6156 -0.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8800 -2.6694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7188 1.8302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2151 -4.9204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9151 -5.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2151 -3.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7181 -2.6698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6151 -4.9204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9151 -2.6704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3164 -1.1702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0170 -3.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6151 -3.4204 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0175 -0.4200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3162 -2.6702 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0168 -4.9200 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7183 -1.1698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5811 -3.4196 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0177 1.0800 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7 6 2 0 0 0 0 8 6 1 0 0 0 0 10 1 1 0 0 0 0 10 7 1 0 0 0 0 11 2 1 0 0 0 0 11 8 2 0 0 0 0 12 3 1 0 0 0 0 13 9 1 0 0 0 0 14 10 2 0 0 0 0 14 11 1 0 0 0 0 15 12 1 0 0 0 0 16 12 1 0 0 0 0 16 13 1 0 0 0 0 16 14 1 0 0 0 0 17 13 2 0 0 0 0 18 15 2 0 0 0 0 19 4 1 0 0 0 0 19 9 1 0 0 0 0 20 5 1 0 0 0 0 20 15 1 0 0 0 0 M END > InChI=1/C15H21NO4/c1-10-7-6-8-11(2)14(10)16(13(17)9-19-4)12(3)15(18)20-5/h6-8,12H,9H2,1-5H3 > Metalaxyl > M01 M02 M03 M04 M05 > M01 M02 M03 M04 > M01 M02 M03 M04 > > M01 NAME: Metalaxyl acid PUBCHEM_CID: 13073467 INCHI: InChI=1S/C14H19NO4/c1-9-6-5-7-10(2)13(9)15(11(3)14(17)18)12(16)8-19-4/h5-7,11H,8H2,1-4H3,(H,17,18) M02 NAME: methanol PUBCHEM_CID: 887 INCHI: InChI=1S/CH4O/c1-2/h2H,1H3 M03 NAME: Methyl N-(2-(hydroxymethyl)-6-methylphenyl)-N-(methoxyacetyl)-DL-alanine PUBCHEM_CID: 20055269 INCHI: InChI=1S/C15H21NO5/c1-10-6-5-7-12(8-17)14(10)16(13(18)9-20-3)11(2)15(19)21-4/h5-7,11,17H,8-9H2,1-4H3 M04 NAME: PUBCHEM_CID: 76543038 INCHI: InChI=1S/C15H21NO5/c1-9-6-7-12(17)10(2)14(9)16(13(18)8-20-4)11(3)15(19)21-5/h6-7,11,17H,8H2,1-5H3 M05 NAME: PUBCHEM_CID: 12878837 INCHI: InChI=1S/C14H19NO4/c1-9-6-5-7-10(2)13(9)15(12(17)8-16)11(3)14(18)19-4/h5-7,11,16H,8H2,1-4H3 > Abass, K. et al. (2007); In vitro metabolism and interactions of the fungicide metalaxyl in human liver preparations; Environ Toxicol Pharmacol.; 23(1):39-47. doi: 10.1016/j.etap.2006.06.004 $$$$ CDK 08101821052D 9 8 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.7500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5 3 2 0 0 0 0 6 3 1 0 0 0 0 7 4 2 0 0 0 0 8 3 1 0 0 0 0 8 4 1 0 0 0 0 9 1 1 0 0 0 0 9 2 1 0 0 0 0 9 4 1 0 0 0 0 M END > InChI=1S/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8) > METFORMIN > > > > > > $$$$ CDK 08101821052D 14 14 0 0 1 0 0 0 0 0999 V2000 -1.3437 -1.9282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6428 -1.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0452 0.3226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2904 -3.0779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2548 -1.9291 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2539 1.0726 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5539 -1.1791 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5534 0.3218 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0447 -1.1782 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.9418 -1.9282 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8031 -4.4876 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2183 2.2215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0671 -2.5885 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0306 0.0615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 5 4 1 1 0 0 0 6 3 1 0 0 0 0 7 5 1 0 0 0 0 8 6 1 0 0 0 0 8 7 1 0 0 0 0 9 1 1 0 0 0 0 9 3 1 0 0 0 0 9 5 1 0 0 0 0 10 2 1 0 0 0 0 11 4 1 0 0 0 0 6 12 1 6 0 0 0 7 13 1 6 0 0 0 8 14 1 1 0 0 0 M END > InChI=1S/C8H17NO5/c10-2-1-9-3-6(12)8(14)7(13)5(9)4-11/h5-8,10-14H,1-4H2/t5-,6+,7-,8-/m1/s1 > MITIGOL > > > > > > $$$$ CDK 08101821052D 21 25 0 0 1 0 0 0 0 0999 V2000 2.7534 -3.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5301 2.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4801 -3.6220 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8301 3.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7801 -4.3720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5101 -0.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0999 -0.5820 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7999 0.1480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5101 0.8980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4801 -2.1220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8099 -1.3520 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1201 2.3680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0801 -3.6220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8001 0.1280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1101 0.8680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0801 -2.1220 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7801 -1.3720 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.1299 -2.0920 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4270 3.1042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5573 -3.3617 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5901 -0.5320 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 2 2 0 0 0 0 5 3 2 0 0 0 0 7 6 1 0 0 0 0 9 2 1 0 0 0 0 9 8 1 0 0 0 0 10 3 1 0 0 0 0 11 8 1 0 0 0 0 11 10 1 0 0 0 0 12 4 1 0 0 0 0 13 5 1 0 0 0 0 14 9 2 0 0 0 0 15 12 2 0 0 0 0 15 14 1 0 0 0 0 16 13 1 0 0 0 0 17 6 1 1 0 0 0 17 10 1 0 0 0 0 17 14 1 6 0 0 0 17 16 1 0 0 0 0 18 1 1 0 0 0 0 18 7 1 0 0 0 0 18 11 1 0 0 0 0 19 12 1 0 0 0 0 13 20 1 6 0 0 0 21 15 1 0 0 0 0 21 16 1 0 0 0 0 M END > InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1 > Morphine > M01 M02 M03 > M01 M02 M03 > > > M01 NAME: Morphine-3-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C23H27NO9/c1-24-7-6-23-10-3-4-12(25)20(23)32-18-13(5-2-9(14(18)23)8-11(10)24)31-22-17(28)15(26)16(27)19(33-22)21(29)30/h2-5,10-12,15-17,19-20,22,25-28H,6-8H2,1H3,(H,29,30)/t10?,11?,12?,15?,16?,17?,19?,20?,22?,23-/m0/s1 M02 NAME: Morphine-N-oxide PUBCHEM_CID: 5362459 (ONLY SAME CONNECTIVITY) INCHI: InChI=1S/C17H19NO4/c1-18(21)7-6-17-10-3-5-13(20)16(17)22-15-12(19)4-2-9(14(15)17)8-11(10)18/h2-5,10-11,13,16,19-20H,6-8H2,1H3/t10?,11?,13?,16?,17-,18?/m0/s1 M03 NAME: Normorphine PUBCHEM_CID: NULL INCHI: InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9?,10?,12?,15?,16-/m0/s1 M04 NAME: morphine-6-glucuronide PUBCHEM_CID: NULL INCHI: NULL M05 NAME: Morphine6-O-sulfate PUBCHEM_CID: NULL INCHI: NULL > https://www.pharmgkb.org/pathway/PA146123006 $$$$ CDK 08101821052D 12 13 0 0 0 0 0 0 0 0999 V2000 1.6616 -1.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6097 1.5414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6700 0.2836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3097 0.7914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6665 1.3985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6097 3.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9149 -1.0150 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0097 3.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0097 1.5414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7108 0.7912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3097 3.7914 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5487 -0.7043 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4 2 2 0 0 0 0 5 3 1 0 0 0 0 6 2 1 0 0 0 0 7 3 1 0 0 0 0 9 4 1 0 0 0 0 9 8 2 0 0 0 0 10 5 1 0 0 0 0 10 9 1 0 0 0 0 11 6 2 0 0 0 0 11 8 1 0 0 0 0 12 1 1 0 0 0 0 12 7 1 0 0 0 0 12 10 1 0 0 0 0 M END > InChI=1/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3 > Nicotine > M01 M02 M03 M04 M05 > M01 M02 M03 > M01 M03 > > M01 NAME: Nicotine N-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C16H22N2O6/c1-17-6-3-5-10(17)9-4-2-7-18(8-9)15-13(21)11(19)12(20)14(24-15)16(22)23/h2,4,7-8,10-15,19-21H,3,5-6H2,1H3/p+1 M02 NAME: nicotine-1'-N-oxide PUBCHEM_CID: 409 INCHI: InChI=1S/C10H14N2O/c1-12(13)7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3 M03 NAME: Nornicotine PUBCHEM_CID: 412 INCHI: InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2 M04 NAME: Nicotine delta-iminium PUBCHEM_CID: 431 INCHI: InChI=1S/C10H13N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6-8,10H,3,5H2,1H3/q+1 M05 NAME: 2'-hydroxynicotine PUBCHEM_CID: 432 INCHI: InChI=1S/C10H14N2O/c1-12-7-3-5-10(12,13)9-4-2-6-11-8-9/h2,4,6,8,13H,3,5,7H2,1H3 > Hukkanen,J. et al. (2005); Metabolism and Disposition Kinetics of Nicotine; Pharmacological Reviews March 2005, 57 (1) 79-115; DOI: https://doi.org/10.1124/pr.57.1.3 $$$$ CDK 08101821052D 24 26 0 0 0 0 0 0 0 0999 V2000 10.8517 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3506 -3.8972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8512 -3.8959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6015 0.0013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3517 -1.2976 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1002 -2.5980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6010 -2.5972 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1006 0.0006 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 -1.2100 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 1.2100 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8500 1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3512 -3.8962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 6 5 2 0 0 0 0 10 1 1 0 0 0 0 10 8 1 0 0 0 0 11 2 1 0 0 0 0 12 5 1 0 0 0 0 12 7 2 0 0 0 0 13 6 1 0 0 0 0 14 7 1 0 0 0 0 14 13 2 0 0 0 0 15 9 1 0 0 0 0 15 11 2 0 0 0 0 16 10 2 0 0 0 0 16 11 1 0 0 0 0 18 8 2 0 0 0 0 18 15 1 0 0 0 0 19 13 1 0 0 0 0 19 17 2 0 0 0 0 20 14 1 0 0 0 0 20 17 1 0 0 0 0 22 3 1 0 0 0 0 22 12 1 0 0 0 0 23 4 1 0 0 0 0 23 16 1 0 0 0 0 24 9 1 0 0 0 0 24 17 1 0 0 0 0 24 21 2 0 0 0 0 M END > InChI=1/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20) > Omeprazole > M01 M02 M03 M04 > M01 M02 M03 M04 > M01 M02 M03 M04 > M02 M03 M04 > M01 NAME: UFIPRAZOLE PUBCHEM_CID: 155794 INCHI: InChI=1/C17H19N3O2S/c1-10-8-18-15(11(2)16(10)22-4)9-23-17-19-13-6-5-12(21-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/f/h20H M02 NAME: 3-Hydroxyomeprazole PUBCHEM_CID: 71587579 INCHI: InChI=1S/C17H19N3O4S/c1-10-7-18-15(12(8-21)16(10)24-3)9-25(22)17-19-13-5-4-11(23-2)6-14(13)20-17/h4-7,21H,8-9H2,1-3H3,(H,19,20) M03 NAME: 5-Hydroxyomeprazole PUBCHEM_CID: 119560 INCHI: InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20) M04 NAME: Omeprazole sulfone PUBCHEM_CID: 145900 INCHI: InChI=1S/C17H19N3O4S/c1-10-8-18-15(11(2)16(10)24-4)9-25(21,22)17-19-13-6-5-12(23-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20) > C-G Regårdh, M Gabrielsson, K-J Hoffman, I Löfberg & I. Skånberg (1985) Pharmacokinetics and metabolism of omeprazole in animals and man - an overview, Scandinavian Journal of Gastroenterology, 20:sup108, 79-94, DOI: 10.3109/00365528509095821 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 22 25 0 0 0 0 0 0 0 0999 V2000 5.5436 0.5889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.3400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2200 -1.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6800 0.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7500 -1.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6800 1.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6800 0.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6800 1.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0985 -2.3248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8073 -3.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2244 -2.3840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2983 -0.7075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2200 -1.2700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2100 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2100 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -0.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7500 -1.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7932 -0.8541 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.8400 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.6915 -2.0712 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2855 -3.0063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 2 0 0 0 0 5 3 1 0 0 0 0 6 4 1 0 0 0 0 8 7 1 0 0 0 0 10 9 2 0 0 0 0 12 1 1 0 0 0 0 13 7 1 0 0 0 0 13 11 1 0 0 0 0 14 5 2 0 0 0 0 15 6 2 0 0 0 0 15 14 1 0 0 0 0 16 8 1 0 0 0 0 17 14 1 0 0 0 0 17 16 2 0 0 0 0 18 13 1 0 0 0 0 18 17 1 0 0 0 0 19 9 1 0 0 0 0 19 12 2 0 0 0 0 20 2 1 0 0 0 0 20 15 1 0 0 0 0 20 16 1 0 0 0 0 21 10 1 0 0 0 0 21 11 1 0 0 0 0 21 12 1 0 0 0 0 22 18 2 0 0 0 0 M END > InChI=1/C18H19N3O/c1-12-19-9-10-21(12)11-13-7-8-16-17(18(13)22)14-5-3-4-6-15(14)20(16)2/h3-6,9-10,13H,7-8,11H2,1-2H3 > Ondansetron > M01 M02 M03 > M01 M02 M03 > M03 > M03 > M01 NAME: 7-Hydroxyondansetron PUBCHEM_CID: 71749264 INCHI: InChI=1S/C18H19N3O2/c1-11-19-7-8-21(11)10-12-3-6-15-17(18(12)23)14-5-4-13(22)9-16(14)20(15)2/h4-5,7-9,12,22H,3,6,10H2,1-2H3 M02 NAME: 6-Hydroxy Ondansetron PUBCHEM_CID: 20152440 INCHI: InChI=1S/C18H19N3O2/c1-11-19-7-8-21(11)10-12-3-5-16-17(18(12)23)14-9-13(22)4-6-15(14)20(16)2/h4,6-9,12,22H,3,5,10H2,1-2H3 M03 NAME: 8-Hydroxy Ondansetron PUBCHEM_CID: 19734439 INCHI: InChI=1S/C18H19N3O2/c1-11-19-8-9-21(11)10-12-6-7-14-16(18(12)23)13-4-3-5-15(22)17(13)20(14)2/h3-5,8-9,12,22H,6-7,10H2,1-2H3 M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1/C17H17N3O/c1-11-18-8-9-20(11)10-12-6-7-15-16(17(12)21)13-4-2-3-5-14(13)19-15/h2-5,8-9,12,19H,6-7,10H2,1H3 > Wang, B. and Zhou, S.-F. (2009); Synthetic and Natural Compounds that Interact with Human Cytochrome P450 1A2 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 4066-4218 $$$$ CDK 08101821052D 18 18 0 0 0 0 0 0 0 0999 V2000 -3.8981 -3.0002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0276 0.5693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5992 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4497 0.3091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1970 -2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8970 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8970 -2.9992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5970 -0.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1970 -0.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5970 -2.2492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4959 0.0010 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.7951 -0.7488 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4957 1.5010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -2.9998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9629 -1.1004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2981 -2.9994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0011 -2.2496 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 -0.9654 -1.1007 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 7 5 1 0 0 0 0 8 6 2 0 0 0 0 9 5 2 0 0 0 0 9 6 1 0 0 0 0 10 7 2 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 12 11 2 0 0 0 0 13 11 2 0 0 0 0 14 3 1 0 0 0 0 15 4 1 0 0 0 0 16 10 1 0 0 0 0 17 14 1 0 0 0 0 17 15 1 0 0 0 0 17 16 1 0 0 0 0 18 17 2 0 0 0 0 M END > InChI=1S/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 > Parathion > M01 M02 M03 M04 > M01 M02 M03 M04 > M01 M02 M03 M04 > M02 M03 > M01 NAME: Phosphorothioic acid O,O-diethyl O-[4-(hydroxyamino)phenyl] ester PUBCHEM_CID: 85843561 INCHI: InChI=1S/C10H16NO4PS/c1-3-13-16(17,14-4-2)15-10-7-5-9(11-12)6-8-10/h5-8,11-12H,3-4H2,1-2H3 M02 NAME: Phosphorothioic acid O,O-diethyl PUBCHEM_CID: NULL INCHI: InChI=1S/C4H11O3PS/c1-3-6-8(5,9)7-4-2/h3-4H2,1-2H3,(H,5,9) M03 NAME: 4-Nitrophenol PUBCHEM_CID: 980 INCHI: InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H M04 NAME: PARAOXON PUBCHEM_CID: 9395 INCHI: InChI=1S/C10H14NO6P/c1-3-15-18(14,16-4-2)17-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 > http://www.inchem.org/documents/jmpr/jmpmono/v95pr13.htm Neal, R.A. (1967) Studies on the metabolism of diethyl 4-nitrophenyl phosphorothionate (parathion) in vitro. Biochem. J., 103, 183-191 Kamataki, T. & Neal, R.A. (1976) Metabolism of diethyl A-nitrophenyl phosphorothionate (parathion) by a reconstituted mixed-function oxidase enzyme system: Studies of covalent binding of the sulfer atom. Mol. Pharmacol., 12, 933-944 $$$$ CDK 08101821052D 18 20 0 0 0 0 0 0 0 0999 V2000 4.4317 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9285 -4.8702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4675 -0.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9187 -3.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4415 -3.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4512 -5.1305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 1.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.1800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9903 -0.8993 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4415 -3.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4772 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5130 -3.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 -0.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 -0.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4772 -2.3097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.5700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0700 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4 1 2 0 0 0 0 5 1 1 0 0 0 0 6 2 1 0 0 0 0 7 2 1 0 0 0 0 8 3 1 0 0 0 0 9 3 1 0 0 0 0 10 4 1 0 0 0 0 11 5 2 0 0 0 0 12 6 1 0 0 0 0 13 7 1 0 0 0 0 14 8 1 0 0 0 0 15 9 1 0 0 0 0 16 10 2 0 0 0 0 16 11 1 0 0 0 0 17 12 1 0 0 0 0 17 13 1 0 0 0 0 17 16 1 0 0 0 0 18 14 1 0 0 0 0 18 15 1 0 0 0 0 18 17 1 0 0 0 0 M END > InChI=1S/C17H25N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11H,2-3,6-9,12-15H2 > Phenncyclidine > M01 M02 M03 > M01 M02 M04 > M01 M02 M04 > > M01 NAME: 4-Phenyl-4-piperidinocyclohexanol PUBCHEM_CID: 162171 INCHI: InChI=1S/C17H25NO/c19-16-9-11-17(12-10-16,15-7-3-1-4-8-15)18-13-5-2-6-14-18/h1,3-4,7-8,16,19H,2,5-6,9-14H2 M02 NAME: 5-(1-Phenylcyclohexylamino)valeric acid PUBCHEM_CID: 173576 INCHI: InChI=1S/C17H25NO2/c19-16(20)11-5-8-14-18-17(12-6-2-7-13-17)15-9-3-1-4-10-15/h1,3-4,9-10,18H,2,5-8,11-14H2,(H,19,20) M03 NAME: 1-(1-Phenylcyclohexyl)-2,3,4,5-tetrahydropyridinium PUBCHEM_CID: 53846933 INCHI: InChI=1S/C17H24N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11,14H,2-3,6-9,12-13,15H2/q+1 M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C17H25NO/c19-16-9-13-18(14-10-16)17(11-5-2-6-12-17)15-7-3-1-4-8-15/h1,3-4,7-8,16,19H,2,5-6,9-14H2 > $$$$ CDK 08101821052D 23 26 0 0 1 0 0 0 0 0999 V2000 5.0433 4.3199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6125 0.9400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4507 3.1203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3200 -2.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0100 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5500 0.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7100 -0.3100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2000 -0.5600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3200 1.6300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8900 0.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0100 2.3900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8900 -2.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0204 2.8200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6200 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2000 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0100 -0.5600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7100 2.0900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2800 0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3200 0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6200 -0.5600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2800 1.6300 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3078 2.0502 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4977 -2.8424 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 4 1 0 0 0 0 7 6 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 13 1 1 0 0 0 0 14 4 1 0 0 0 0 14 12 2 0 0 0 0 15 8 1 0 0 0 0 15 12 1 0 0 0 0 16 5 1 0 0 0 0 17 6 1 1 0 0 0 17 13 1 0 0 0 0 18 7 1 0 0 0 0 18 16 1 0 0 0 0 19 9 1 0 0 0 0 19 16 1 0 0 0 0 20 2 1 1 0 0 0 20 10 1 0 0 0 0 20 14 1 0 0 0 0 20 19 1 0 0 0 0 21 3 1 1 0 0 0 21 11 1 0 0 0 0 21 17 1 0 0 0 0 21 18 1 0 0 0 0 22 13 2 0 0 0 0 23 15 2 0 0 0 0 M END > InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1 > Progesterone > M01 M02 M03 M04 M05 M06 M07 M08 M09 M10 M11 > M01 M02 M03 M06 M07 M08 M09 M10 M11 > M01 M10 M11 > > M01 NAME: 5beta-pregnane-3,20-dione PUBCHEM_CID: NULL INCHI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14,16-19H,4-12H2,1-3H3/t14?,16?,17?,18?,19?,20-,21+/m0/s1 M02 NAME: 21-OH-progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15?,16?,17?,18?,20-,21-/m0/s1 M03 NAME: 17-OH-hydroxy progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16?,17?,18?,19-,20-,21?/m0/s1 M04 NAME: acetic acid PUBCHEM_CID: 21980959 INCHI: InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) M05 NAME: [1beta-3H] androstenedione PUBCHEM_CID: 6432604 INCHI: InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14?,15?,16?,18-,19-/m0/s1 M06 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-12(22)15-4-5-16-19-17(7-9-21(15,16)3)20(2)8-6-14(23)10-13(20)11-18(19)24/h10,15-19,24H,4-9,11H2,1-3H3/t15?,16?,17?,18?,19?,20-,21+/m0/s1 M07 NAME: 11-beta-Hydroxyprogesterone PUBCHEM_CID: 44135599 INCHI: InChI=1S/C21H30O3/c1-12(22)16-6-7-17-15-5-4-13-10-14(23)8-9-20(13,2)19(15)18(24)11-21(16,17)3/h10,15-19,24H,4-9,11H2,1-3H3/t15?,16?,17?,18?,19?,20-,21+/m0/s1 M08 NAME: 16alpha-OH-progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-12(22)19-18(24)11-17-15-5-4-13-10-14(23)6-8-20(13,2)16(15)7-9-21(17,19)3/h10,15-19,24H,4-9,11H2,1-3H3/t15?,16?,17?,18?,19?,20-,21-/m0/s1 M09 NAME: 2beta-OH-progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-12(22)15-6-7-16-14-5-4-13-10-18(23)19(24)11-21(13,3)17(14)8-9-20(15,16)2/h10,14-17,19,24H,4-9,11H2,1-3H3/t14?,15?,16?,17?,19?,20-,21+/m1/s1 M10 NAME: 6-OH-progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O3/c1-12(22)15-4-5-16-14-11-19(24)18-10-13(23)6-8-21(18,3)17(14)7-9-20(15,16)2/h10,14-17,19,24H,4-9,11H2,1-3H3/t14?,15?,16?,17?,19?,20-,21-/m1/s1 M11 NAME: 20-Dihydroprogesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13?,16?,17?,18?,19?,20-,21+/m0/s1 M12 NAME: 15alpha-OH-progesterone PUBCHEM_CID: NULL INCHI: InChI=1S/C21H30O4/c1-12(22)21(25)11-17(24)18-15-5-4-13-10-14(23)6-8-19(13,2)16(15)7-9-20(18,21)3/h10,15-18,24-25H,4-9,11H2,1-3H3/t15?,16?,17-,18?,19-,20-,21?/m0/s1 > PMID:685271 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 Muhammad Akhtar et al. (2011); A review of mechanistic studies on aromatase (CYP19) and 17 -hydroxylase-17,20-lyase (CYP17); Journal of Steroid Biochemistry & Molecular Biology 125 (2011) 2–12; doi:10.1016/j.jsbmb.2010.11.003 PMID:725981 Storbeck KH, Swart P, Africander D, Conradie R, Louw R, Swart AC (2011). 16α-hydroxyprogesterone: origin, biosynthesis and receptor interaction. Mol. Cell. Endocrinol. 336 (1-2): 92–101. PMID 21095220. doi:10.1016/j.mce.2010.11.016 PMID:655220 $$$$ CDK 08101821052D 15 15 0 0 1 0 0 0 0 0999 V2000 -5.2505 1.1357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0441 2.5076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3512 0.6479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7100 -1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 1.2900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7700 -1.2900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7100 1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9592 -0.0890 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7513 1.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9592 0.0890 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4600 -0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4600 0.0400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7513 -1.1848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0441 -2.5076 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2505 -1.1357 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 4 1 0 0 0 0 7 5 2 0 0 0 0 9 1 1 0 0 0 0 9 2 1 0 0 0 0 9 8 1 0 0 0 0 10 3 1 6 0 0 0 11 4 2 0 0 0 0 11 5 1 0 0 0 0 11 8 1 0 0 0 0 12 6 2 0 0 0 0 12 7 1 0 0 0 0 12 10 1 0 0 0 0 13 10 1 0 0 0 0 14 13 2 0 0 0 0 15 13 1 0 0 0 0 M END > InChI=1/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)/t10-/s2 > R-Ibuprofen > M01 M02 M03 M04 > M01 M02 M03 M04 > M01 M02 M04 > > M01 NAME: R-Ibuprofen glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C19H26O8/c1-9(2)8-11-4-6-12(7-5-11)10(3)18(25)27-19-15(22)13(20)14(21)16(26-19)17(23)24/h4-7,9-10,13-16,19-22H,8H2,1-3H3,(H,23,24) M02 NAME: 1-Hydroxyibuprofen PUBCHEM_CID: 45117195 INCHI: InChI=1S/C13H18O3/c1-8(2)12(14)11-6-4-10(5-7-11)9(3)13(15)16/h4-9,12,14H,1-3H3,(H,15,16) M03 NAME: 2-Hydroxyibuprofen PUBCHEM_CID: 10443535 INCHI: InChI=1S/C13H18O3/c1-9(12(14)15)11-6-4-10(5-7-11)8-13(2,3)16/h4-7,9,16H,8H2,1-3H3,(H,14,15) M04 NAME: 3-Hydroxyibuprofen PUBCHEM_CID: 71312545 INCHI: InChI=1S/C13H18O3/c1-9(8-14)7-11-3-5-12(6-4-11)10(2)13(15)16/h3-6,9-10,14H,7-8H2,1-2H3,(H,15,16) > Neunzig, I. et al. (2012); Production and NMR analysis of the human ibuprofen metabolite 3-hydroxyibuprofen; J Biotechnol. 2012 Feb 10;157(3):417-20. doi: 10.1016/j.jbiotec.2011.12.016; PMID: 22226725 Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 15 16 0 0 0 0 0 0 0 0999 V2000 -2.3100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0100 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3100 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2900 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 0.7504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2070 1.5006 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -5.8724 -0.3985 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -3.9441 -0.3988 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 4.1000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 -1.2100 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6089 1.5002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7200 1.2100 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 4 1 1 0 0 0 0 4 3 2 0 0 0 0 5 2 1 0 0 0 0 6 3 1 0 0 0 0 6 5 2 0 0 0 0 9 8 1 0 0 0 0 10 8 1 0 0 0 0 11 8 1 0 0 0 0 12 7 2 0 0 0 0 13 5 1 0 0 0 0 13 7 1 0 0 0 0 14 4 1 0 0 0 0 14 8 1 0 0 0 0 15 6 1 0 0 0 0 15 7 1 0 0 0 0 M END > InChI=1S/C8H5F3N2OS/c9-8(10,11)14-4-1-2-5-6(3-4)15-7(12)13-5/h1-3H,(H2,12,13) > Riluzole > M01 M02 M03 > M01 M02 M03 > M03 > M03 > M01 NAME: 2-Amino-6-trifluoromethoxybenzothiazol-5-ol PUBCHEM_CID: NULL INCHI: InChI=1S/C14H13F3N2O7S/c15-14(16,17)26-4-1-2-5-6(3-4)27-13(18-5)19-11-9(22)7(20)8(21)10(25-11)12(23)24/h1-3,7-11,20-22H,(H,18,19)(H,23,24) M02 NAME: PUBCHEM_CID: 19063893 INCHI: InChI=1S/C8H5F3N2O2S/c9-8(10,11)15-5-2-6-3(1-4(5)14)13-7(12)16-6/h1-2,14H,(H2,12,13) M03 NAME: N-Hydroxy Riluzole PUBCHEM_CID: 9859774 INCHI: InChI=1S/C8H5F3N2O2S/c9-8(10,11)15-4-1-2-5-6(3-4)16-7(12-5)13-14/h1-3,14H,(H,12,13) M04 NAME: 4-OH-riluzole PUBCHEM_CID: NULL INCHI: InChI=1S/C8H5F3N2O2S/c9-8(10,11)15-3-1-4(14)6-5(2-3)16-7(12)13-6/h1-2,14H,(H2,12,13) M05 NAME: 7-OH-riluzole PUBCHEM_CID: NULL INCHI: InChI=1S/C8H5F3N2O2S/c9-8(10,11)15-4-2-1-3-6(5(4)14)16-7(12)13-3/h1-2,14H,(H2,12,13) > Wang, B. and Zhou, S.F. (2009); Synthetic and Natural Compounds that Interact with Human Cytochrome P450 1A2 and Implications in Drug Development; Current Medicinal Chemistry; Vol. 16, No. 31; PMID:19754423 Sanderink, GJ. et al. (1997); Involvement of human CYP1A isoenzymes in the metabolism and drug interactions of riluzole in vitro; J Pharmacol Exp Ther.;282(3):1465-72; PMID:9316860 $$$$ CDK 08101821052D 17 20 0 0 1 0 0 0 0 0999 V2000 -4.4700 0.7100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3900 -0.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4600 -0.7900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3700 0.7200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1800 1.4700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1000 -1.5300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1500 -1.5300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0600 1.4600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6800 0.5200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7300 1.7700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8100 -1.8300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 1.7800 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6800 -1.8500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8600 0.7400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7700 -0.8000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8600 -0.7600 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7700 0.7000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 5 1 1 0 0 0 0 6 2 1 0 0 0 0 7 3 1 0 0 0 0 8 4 1 0 0 0 0 12 9 1 0 0 0 0 12 10 1 0 0 0 0 13 9 1 0 0 0 0 13 11 1 0 0 0 0 14 5 1 0 0 0 0 14 12 1 0 0 0 0 15 6 1 0 0 0 0 15 13 1 0 0 0 0 16 7 1 0 0 0 0 16 11 1 0 0 0 0 16 14 1 0 0 0 0 17 8 1 0 0 0 0 17 10 1 0 0 0 0 17 15 1 0 0 0 0 M END > InChI=1S/C15H26N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h12-15H,1-11H2/t12-,13-,14-,15+/m0/s1 > Sparteine > M01 > M01 > > > M01 NAME: Sparteine N-oxide PUBCHEM_CID: NULL INCHI: InChI=1S/C15H26N2O/c18-17-8-4-2-6-15(17)12-9-13(11-17)14-5-1-3-7-16(14)10-12/h12-15H,1-11H2 M02 NAME: 5-Dihydrosparteine PUBCHEM_CID: NULL INCHI: InChI=1/C15H24N2/c1-3-7-16-11-13-9-12(14(16)5-1)10-17-8-4-2-6-15(13)17/h5,12-13,15H,1-4,6-11H2/t12-,13-,15-/s2 > Ebner, T et al. (1995); Mechanism of cytochrome P450 2D6-catalyzed sparteine metabolism in humans; Mol Pharmacol. 1995 Dec;48(6):1078-86; PMID:8848008 Zhou, SF. (2009); Clin Pharmacokinet ; 48 (12): 761-804 $$$$ CDK 08101821052D 17 18 0 0 0 0 0 0 0 0999 V2000 -3.8549 1.9661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5026 4.3380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5588 1.9638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1309 3.7288 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1872 1.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2801 2.6504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3885 1.6506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7165 3.4555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9732 2.2372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0189 1.9004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0871 4.0650 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2927 0.4406 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3895 2.5099 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.5232 0.5861 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4409 0.3837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7856 0.2748 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6027 1.6277 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 4 2 1 0 0 0 0 5 3 2 0 0 0 0 7 1 1 0 0 0 0 7 6 2 0 0 0 0 8 2 2 0 0 0 0 8 3 1 0 0 0 0 9 4 2 0 0 0 0 9 5 1 0 0 0 0 10 6 1 0 0 0 0 11 8 1 0 0 0 0 12 10 2 0 0 0 0 13 10 1 0 0 0 0 16 7 1 0 0 0 0 16 12 1 0 0 0 0 17 9 1 0 0 0 0 17 13 1 0 0 0 0 17 14 2 0 0 0 0 17 15 2 0 0 0 0 M END > InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13) > Sulfamethoxazole > M01 M02 M03 M04 > M01 M02 M03 M04 > M03 M04 > > M01 NAME: N4-Acetylsulfamethoxazole PUBCHEM_CID: 65280 INCHI: InChI=1S/C12H13N3O4S/c1-8-7-12(14-19-8)15-20(17,18)11-5-3-10(4-6-11)13-9(2)16/h3-7H,1-2H3,(H,13,16)(H,14,15) M02 NAME: Sulfamethoxazole N1-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C16H19N3O9S/c1-7-6-10(18-28-7)19-29(25,26)9-4-2-8(3-5-9)17-15-13(22)11(20)12(21)14(27-15)16(23)24/h2-6,11-15,17,20-22H,1H3,(H,18,19)(H,23,24) M03 NAME: N-[5-(Hydroxymethyl)isoxazol-3-yl]-4-aminobenzenesulfonamide PUBCHEM_CID: 10355717 INCHI: InChI=1S/C10H11N3O4S/c11-7-1-3-9(4-2-7)18(15,16)13-10-5-8(6-14)17-12-10/h1-5,14H,6,11H2,(H,12,13) M04 NAME: Sulfamethoxazole hydroxylamine PUBCHEM_CID: 114821 INCHI: InChI=1S/C10H11N3O4S/c1-7-6-10(12-17-7)13-18(15,16)9-4-2-8(11-14)3-5-9/h2-6,11,14H,1H3,(H,12,13) > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 21 23 0 0 0 0 0 0 0 0999 V2000 -0.5568 -3.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1096 6.0776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3245 5.6351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2106 5.0575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6577 4.1726 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8773 3.5950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8800 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5800 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5800 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5568 3.1525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8800 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2800 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2800 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 1.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3500 -1.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1789 1.5002 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -2.3500 1.3500 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8900 -1.6900 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2879 -2.5207 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2 0 0 0 0 4 2 1 0 0 0 0 5 3 1 0 0 0 0 6 4 2 0 0 0 0 8 7 2 0 0 0 0 10 5 2 0 0 0 0 10 6 1 0 0 0 0 11 7 1 0 0 0 0 11 9 2 0 0 0 0 12 9 1 0 0 0 0 13 8 1 0 0 0 0 13 12 2 0 0 0 0 14 10 1 0 0 0 0 14 12 1 0 0 0 0 16 15 1 0 0 0 0 17 11 1 0 0 0 0 18 14 2 0 0 0 0 18 15 1 0 0 0 0 19 1 1 0 0 0 0 19 13 1 0 0 0 0 19 16 1 0 0 0 0 20 15 1 0 0 0 0 21 16 2 0 0 0 0 M END > InChI=1S/C16H13ClN2O2/c1-19-13-8-7-11(17)9-12(13)14(18-15(20)16(19)21)10-5-3-2-4-6-10/h2-9,15,20H,1H3 > Temazepam > M01 > M01 > M01 > M01 > M01 NAME: Tazepam PUBCHEM_CID: NULL INCHI: InChI=1S/C15H11ClN2O2/c16-10-6-7-12-11(8-10)13(9-4-2-1-3-5-9)18-15(20)14(19)17-12/h1-8,15,20H,(H,17,19) M02 NAME: Temazepam O-glucuronide PUBCHEM_CID: NULL INCHI: NULL > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 11 11 0 0 0 0 0 0 0 0999 V2000 -3.5376 -0.2051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2386 -2.4551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9576 2.0449 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3590 2.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9400 1.2958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6590 -0.2059 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2386 -0.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6585 1.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9395 -0.2051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3600 -0.9559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3597 -2.4559 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 4 2 0 0 0 0 7 1 1 0 0 0 0 7 2 1 0 0 0 0 8 3 1 0 0 0 0 8 4 1 0 0 0 0 8 6 2 0 0 0 0 9 5 1 0 0 0 0 9 7 1 0 0 0 0 10 6 1 0 0 0 0 10 9 2 0 0 0 0 11 10 1 0 0 0 0 M END > InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-7,11H,1-3H3 > Thymol > M01 M02 M03 M04 M05 M06 M07 M08 > M01 M02 M03 M05 M07 > M03 M05 M07 > M03 M05 > M01 NAME: thymol O-glucuronide PUBCHEM_CID: 346530 INCHI: InChI=1S/C16H22O7/c1-7(2)9-5-4-8(3)6-10(9)22-16-13(19)11(17)12(18)14(23-16)15(20)21/h4-7,11-14,16-19H,1-3H3,(H,20,21) M02 NAME: thymol O-sulfate PUBCHEM_CID: 12456386 INCHI: InChI=1S/C10H14O4S/c1-7(2)9-5-4-8(3)6-10(9)14-15(11,12)13/h4-7H,1-3H3,(H,11,12,13) M03 NAME: p-Cymene-3,8-diol PUBCHEM_CID: NULL INCHI: InChI=1S/C10H14O2/c1-7-4-5-8(9(11)6-7)10(2,3)12/h4-6,11-12H,1-3H3 M04 NAME: Thymoquinol PUBCHEM_CID: NULL INCHI: InChI=1S/C10H14O2/c1-6(2)8-5-9(11)7(3)4-10(8)12/h4-6,11-12H,1-3H3 M05 NAME: 7-Hydroxythymol PUBCHEM_CID: 14002478 INCHI: InChI=1S/C10H14O2/c1-7(2)9-4-3-8(6-11)5-10(9)12/h3-5,7,11-12H,6H2,1-2H3 M06 NAME: p-Cymene-2,3-diol PUBCHEM_CID: 95873 INCHI: InChI=1S/C10H14O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h4-6,11-12H,1-3H3 M07 NAME: 9-Hydroxythymol PUBCHEM_CID: 14432748 INCHI: InChI=1S/C10H14O2/c1-7-3-4-9(8(2)6-11)10(12)5-7/h3-5,8,11-12H,6H2,1-2H3 M08 NAME: p-Cymen-8-en-3-ol PUBCHEM_CID: 6429037 INCHI: InChI=1S/C10H12O/c1-7(2)9-5-4-8(3)6-10(9)11/h4-6,11H,1H2,2-3H3 > Walter Jäger and Martina Höferl; Metabolism of Terpenoids in Animal Models and Humans; p. 265; in Handbook of Essential Oils: Science, Technology, and Applications $$$$ CDK 08101821052D 21 24 0 0 1 0 0 0 0 0999 V2000 -1.6300 0.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4272 3.1517 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 -2.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6900 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5700 0.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2300 -0.5900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3300 1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9300 0.1600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 2.4100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9300 -2.8400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6300 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2300 -2.0900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9700 -0.5900 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.2700 0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3300 0.1600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6900 2.1200 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6300 -0.5900 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2700 1.6600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5289 -2.8402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9890 2.8700 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 3 1 0 0 0 0 6 5 1 0 0 0 0 9 7 1 0 0 0 0 10 8 1 0 0 0 0 12 3 1 0 0 0 0 12 11 2 0 0 0 0 13 7 1 0 0 0 0 13 11 1 0 0 0 0 14 4 1 0 0 0 0 15 5 1 0 0 0 0 15 14 1 0 0 0 0 16 8 1 0 0 0 0 16 14 1 0 0 0 0 17 6 1 1 0 0 0 18 1 1 1 0 0 0 18 9 1 0 0 0 0 18 12 1 0 0 0 0 18 16 1 0 0 0 0 19 2 1 1 0 0 0 19 10 1 0 0 0 0 19 15 1 0 0 0 0 19 17 1 0 0 0 0 20 13 2 0 0 0 0 21 17 1 0 0 0 0 M END > InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 > Testosterone > M01 M02 M03 M04 M05 M06 M07 M08 M09 > M01 M02 M03 M06 M08 M09 M10 > M01 M02 M03 M08 > M03 > M01 NAME: 5-Dihydrotestosterone PUBCHEM_CID: NULL INCHI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12?,14?,15?,16?,17?,18-,19-/m0/s1 M02 NAME: 5-Androstenediol PUBCHEM_CID: 44358133 INCHI: InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-17,20-21H,3-10H2,1-2H3/t13?,14?,15?,16?,17?,18-,19-/m0/s1 M03 NAME: 17-Ketotestosterone (Androstenedione) PUBCHEM_CID: NULL INCHI: InChI=1S/C19H27O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17H,3-10H2,1-2H3/t14?,15?,16?,18-,19-/m0/s1 M04 NAME: Estradiol PUBCHEM_CID: 43912931 INCHI: InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14?,15?,16?,17?,18-/m0/s1 M05 NAME: methanol PUBCHEM_CID: NULL INCHI: InChI=1S/CH4O/c1-2/h2H,1H3 M06 NAME: 11-OH-testosterone PUBCHEM_CID: 68057362 INCHI: InChI=1S/C19H28O3/c1-18-8-7-12(20)9-11(18)3-4-13-14-5-6-16(22)19(14,2)10-15(21)17(13)18/h9,13-17,21-22H,3-8,10H2,1-2H3/t13?,14?,15?,16?,17?,18-,19-/m0/s1 M07 NAME: Testosterone 17-O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C25H36O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31)/t14?,15?,16?,17?,18?,19?,20?,21?,23?,24-,25-/m0/s1 M08 NAME: 6-Hydroxytestosterone PUBCHEM_CID: NULL INCHI: InChI=1S/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12?,13?,14?,16?,17?,18-,19+/m1/s1 M09 NAME: 2-Hydroxytestosterone PUBCHEM_CID: NULL INCHI: InChI=1S/C19H28O3/c1-18-8-7-14-12(13(18)5-6-17(18)22)4-3-11-9-15(20)16(21)10-19(11,14)2/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12?,13?,14?,16?,17?,18-,19-/m0/s1 M10 NAME: 15-OH-testosterone PUBCHEM_CID: NULL INCHI: InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)16(22)10-15(21)17(13)19/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14+,15?,16+,17-,18+,19-/m1/s1 M11 NAME: 1-Hydroxytestosterone PUBCHEM_CID: NULL INCHI: InChI=1S/C19H28O3/c1-18-8-7-15-13(14(18)5-6-16(18)21)4-3-11-9-12(20)10-17(22)19(11,15)2/h9,13-17,21-22H,3-8,10H2,1-2H3/t13-,14-,15-,16-,17?,18-,19-/m0/s1 > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 Sten, T. et al. (2009); UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly; Drug Metab Dispos. 2009 Feb;37(2):417-23. doi: 10.1124/dmd.108.024844; PMID:19022937 $$$$ CDK 08101821052D 10 9 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 5 3 1 0 0 0 0 6 4 1 0 0 0 0 7 5 1 0 0 0 0 7 6 1 0 0 0 0 8 7 1 0 0 0 0 9 8 2 0 0 0 0 10 8 1 0 0 0 0 M END > InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) > Valproic acid > M01 M02 M03 M04 > M01 M02 M03 M05 > M01 M02 M03 > > M01 NAME: Valproic Acid beta-D-Glucuronide PUBCHEM_CID: 20982145 INCHI: InChI=1S/C14H24O8/c1-3-5-7(6-4-2)13(20)22-14-10(17)8(15)9(16)11(21-14)12(18)19/h7-11,14-17H,3-6H2,1-2H3,(H,18,19) M02 NAME: 4-Hydroxyvalproic acid PUBCHEM_CID: 134467 INCHI: InChI=1S/C8H16O3/c1-3-4-7(8(10)11)5-6(2)9/h6-7,9H,3-5H2,1-2H3,(H,10,11) M03 NAME: 5-Hydroxyvalproic acid PUBCHEM_CID: 135244 INCHI: InChI=1S/C8H16O3/c1-2-4-7(8(10)11)5-3-6-9/h7,9H,2-6H2,1H3,(H,10,11) M04 NAME: 2-Propyl-4-pentenoic acid PUBCHEM_CID: 104896 INCHI: InChI=1S/C8H14O2/c1-3-5-7(6-4-2)8(9)10/h3,7H,1,4-6H2,2H3,(H,9,10) M05 NAME: 3-OH-VPA PUBCHEM_CID: NULL INCHI: NULL > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 Brown, C.M. et al. (2008); Cytochromes P450: A Structure-Based Summary of Biotransformations Using Representative Substrates; Drug Metabolism Reviews, 40:1, 1-100, DOI: 10.1080/03602530701836662; PMID:18259985; PMID:18259985 $$$$ CDK 08101821052D 21 23 0 0 0 0 0 0 0 0999 V2000 -6.0756 -2.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2400 -0.3000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9400 1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1100 -1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5100 1.6600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8900 1.2800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4600 1.7300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1400 -1.2100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8000 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7121 -0.5628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2700 -0.1500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7100 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6800 -0.8300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7000 -1.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3300 0.6800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3800 0.6000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7906 0.4796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3228 -3.3246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4271 1.9349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2327 0.0668 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0300 1.2800 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 3 2 2 0 0 0 0 4 2 1 0 0 0 0 5 3 1 0 0 0 0 7 6 2 0 0 0 0 10 1 1 0 0 0 0 11 6 1 0 0 0 0 11 8 2 0 0 0 0 11 10 1 0 0 0 0 12 8 1 0 0 0 0 12 9 1 0 0 0 0 13 4 2 0 0 0 0 14 9 1 0 0 0 0 14 13 1 0 0 0 0 15 7 1 0 0 0 0 15 12 2 0 0 0 0 16 5 2 0 0 0 0 16 13 1 0 0 0 0 17 10 1 0 0 0 0 18 14 2 0 0 0 0 19 17 2 0 0 0 0 20 17 1 0 0 0 0 21 15 1 0 0 0 0 21 16 1 0 0 0 0 M END > InChI=1/C17H14O3S/c1-10(17(19)20)11-6-7-15-12(8-11)9-14(18)13-4-2-3-5-16(13)21-15/h2-8,10H,9H2,1H3,(H,19,20) > Zaltoprofen > M01 M02 M03 > M01 M02 M03 > M01 M02 M03 > M03 > M01 NAME: PUBCHEM_CID: 69583459 INCHI: InChI=1S/C17H16O3S/c1-10(17(19)20)11-6-7-15-12(8-11)9-14(18)13-4-2-3-5-16(13)21-15/h2-8,10,14,18H,9H2,1H3,(H,19,20) M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C23H22O9S/c1-10(22(30)32-23-19(27)17(25)18(26)20(31-23)21(28)29)11-6-7-15-12(8-11)9-14(24)13-4-2-3-5-16(13)33-15/h2-8,10,17-20,23,25-27H,9H2,1H3,(H,28,29) M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C17H14O4S/c1-10(17(19)20)11-6-7-15-12(8-11)9-14(18)13-4-2-3-5-16(13)22(15)21/h2-8,10H,9H2,1H3,(H,19,20) > Zhou, S.F. et al. (2009); Substrates, Inducers, Inhibitors and Structure-Activity Relationships of Human Cytochrome P450 2C9 and Implications in Drug Development; Current Medicinal Chemistry, 2009, 16, 3480-3675 $$$$ CDK 08101821052D 23 23 0 0 1 0 0 0 0 0999 V2000 5.2185 1.3785 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3000 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2543 -1.2716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7413 1.6389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2899 -2.4204 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3000 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8127 -2.1596 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3000 -0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5989 -1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4509 4.0587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0264 4.3190 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4149 5.2078 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7772 0.4897 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.9641 2.6492 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.7315 -1.5324 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2281 3.0483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5888 -3.1707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3355 -2.4198 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5987 -3.0002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8981 -0.7504 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4 1 1 0 0 0 0 5 2 1 0 0 0 0 6 3 1 0 0 0 0 7 2 2 0 0 0 0 8 5 1 0 0 0 0 9 6 1 0 0 0 0 10 8 1 0 0 0 0 10 9 1 6 0 0 0 11 7 1 0 0 0 0 13 12 2 0 0 0 0 14 12 1 0 0 0 0 15 4 2 0 0 0 0 8 15 1 1 0 0 0 5 16 1 6 0 0 0 16 12 1 0 0 0 0 17 3 1 0 0 0 0 18 4 1 4 0 0 0 6 19 1 1 0 0 0 9 20 1 1 0 0 0 21 11 2 0 0 0 0 22 11 1 0 0 0 0 23 7 1 0 0 0 0 23 10 1 0 0 0 0 M END > InChI=1S/C12H20N4O7/c1-4(18)15-8-5(16-12(13)14)2-7(11(21)22)23-10(8)9(20)6(19)3-17/h2,5-6,8-10,17,19-20H,3H2,1H3,(H,15,18)(H,21,22)(H4,13,14,16)/t5-,6+,8+,9+,10+/m0/s1 > Zanamivir > > > > > > $$$$