name of parent molecule,DOI,parent SMILES,metabolite SMILES (separated by space)
osthole,10.1080/00498254.2017.1306660 ,"C1=CC(OC)=C(C/C=C(\C)/C)C2OC(=O)C=CC1=2","C1=CC(O)=C(C/C=C(\C)/C)C2OC(=O)C=CC1=2" "C1=CC(OC)=C(/C=C/C(=C)C)C2OC(=O)C=CC1=2" "C1=CC(OC)=C(C/C=C(\C)/CO)C2OC(=O)C=CC1=2" "C1=CC(OC)=C(C/C=C(\C)/C)C2OC(=O)C(O)=CC1=2" "C1=CC(OC)=C(C/C=C(\C)/C)C2OC(O)C(CC(O)=O)=CC1=2"
TAK-438,10.1080/00498254.2016.1203505 ,"C1=CC=CC(F)=C1C1=CC(CNC)=CN1S(C1=CC=CN=C1)(=O)=O","C1=CC=CC(F)=C1C1=CC(CN)=CN1S(C1=CC=CN=C1)(=O)=O" "C1=CC=CC(F)=C1C1=CC(C(=O)O)=CN1S(C1=CC=CN=C1)(=O)=O" "C1=CC=CC(F)=C1C1=CC(/C=[NH0+](\[OH0-])/C)=CN1S(C1=CC=CN=C1)(=O)=O"
suvorexant,10.3109/00498254.2015.1129565 ,"C1=CC(Cl)=CC2N=C(N3CCN(C(=O)C4=CC(C)=CC=C4N4N=CC=N4)C(C)CC3)OC1=2","C1=C(O)C(Cl)=CC2N=C(N3CCN(C(=O)C4=CC(C)=CC=C4N4N=CC=N4)C(C)CC3)OC1=2" "C1=CC(Cl)=CC2N=C(N3CCN(C(=O)C4=CC(CO)=CC=C4N4N=CC=N4)C(C)CC3)OC1=2" "C1=CC(Cl)=CC2N=C(N3CCN(C(=O)C4=CC(C)=CC=C4N4N=CC=N4)C(CO)CC3)OC1=2"
TSAHC,10.3109/00498254.2015.1081306 ,"C1=C(C)C=CC(S(=O)(NC2=CC=C(C(/C=C/C3=CC=C(O)C=C3)=O)C=C2)=O)=C1","C1=C(CO)C=CC(S(=O)(NC2=CC=C(C(/C=C/C3=CC=C(O)C=C3)=O)C=C2)=O)=C1" "C1=C(C)C=CC(S(=O)(NC2=CC=C(C(/C=C/C3=CC=C(O)C(O)=C3)=O)C=C2)=O)=C1"
ripasudil,10.3109/00498254.2015.1096981 ,"C(S(=O)(N1[C@@H](C)CNCCC1)=O)1=CC=CC2C=NC=C(F)C1=2","C(S(=O)(N1[C@@H](C)CNC(=O)CC1)=O)1=CC=CC2C=NC=C(F)C1=2" "C(S(=O)(N1[C@@H](C)C[NH0+]([OH0-])=CCC1)=O)1=CC=CC2C=NC=C(F)C1=2"
crizotinib,10.3109/00498254.2014.941964 ,"C(Cl)1=C(F)C=CC(Cl)=C1[C@@H](C)OC1C(N)=NC=C(C2=CN(C3CCNCC3)N=C2)C=1","OC1C(N)=NC=C(C2=CN(C3CCNCC3)N=C2)C=1"
PBPA,10.3109/00498254.2013.850552 ,"C(C1=CC=C(CNCC(C)C)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1","C(C1=CC=C(CNCC(C)CO)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1" "C(C1=CC=C(CNCC(O)(C)C)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1" "C(C1=CC=C(CNCC(C)C)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1O" "C(C1=CC=C(CNCC(C)C)C=C1)1=CC=CC=C1S(=O)(=O)N1CCC(O)C1" "C(C1=CC=C(C(=O)NCC(C)C)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1" "C(C1=CC=C(CN)C=C1)1=CC=CC=C1S(=O)(=O)N1CCCC1"
S002-333,10.3109/00498254.2013.831958 ,"C1=CC=CC2NC3CN(S(C4=CC=C(OC)C=C4)(=O)=O)C(C(=O)N)CC=3C1=2","C1=CC=CC2NC3CN(S(C4=CC=C(OC)C(O)=C4)(=O)=O)C(C(=O)N)CC=3C1=2" "C1=CC=CC2NC3CN(S(C4=CC=C(O)C=C4)(=O)=O)C(C(=O)N)CC=3C1=2" "C1=CC=CC2NC3CN(S(C4=CC=C(OC)C=C4)(=O)=O)C(C(=O)N)=CC=3C1=2"
metoclopramide,10.3109/00498254.2013.835885 ,"C1=C(Cl)C(N)=CC(OC)=C1C(=O)NCCN(CC)CC","C1=C(Cl)C([NH0+](=O)[OH0-])=CC(OC)=C1C(=O)NCCN(CC)CC" "C1=C(Cl)C(N)=CC(OC)=C1C(=O)NCCNCC"
teneligliptin,10.3109/00498254.2013.816891 ,"C1=C(N2C(N3CCN([C@@H0]([HH0])4C[C@@H0]([HH0])(C(=O)N5CSCC5)NC4)CC3)=CC(C)=N2)C=CC=C1","C1=C(N2C(N3CCN([C@@H0]([HH0])4C[C@@H0]([HH0])(C(=O)N5CS(=O)CC5)NC4)CC3)=CC(C)=N2)C=CC=C1" "C1=C(N2C(N3CCN([C@@H0]([HH0])4C[C@@H0]([HH0])(C(=O)N5CSCC5)NC4)CC3)=CC(CO)=N2)C=CC=C1" "C1=C(N2C(N3CCN([C@@H0]([HH0])4C[C@@H0]([HH0])(C(O)=O)NC4)CC3)=CC(C)=N2)C=CC=C1"
venetoclax,10.1124/dmd.116.071613 ,"C1=CC(Cl)=CC=C1C1CC(C)(C)CCC=1CN1CCN(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1","C1=CC(Cl)=CC=C1C1CC(C)(C)CCC=1CN1CC(=O)N(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1" "C1=CC(Cl)=CC=C1C1CC(CO)(C)CCC=1CN1CCN(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1" "C1=CC(Cl)=CC=C1C1C(O)C(C)(C)CCC=1CN1CCN(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1" "C1=CC(Cl)=CC=C1C1CC(C)(C)CC(O)C=1CN1CCN(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1" "C1=CC(Cl)=CC=C1C1CC(C)(C)CCC=1C[NH0+]([OH0-])1CCN(C2=CC(OC3=CN=C4NC=CC4=C3)=C(C(=O)NS(=O)(=O)C3=CC=C(NCC4CCOCC4)C([NH0+]([OH0-])=O)=C3)C=C2)CC1"
CINPA1,10.1124/dmd.116.071993 ,"C1C2CCC3=CC=C(NC(=O)OCC)C=C3N(C(CN(CC)CC)=O)C=2C=CC=1","C1C2CCC3=CC=C(NC(=O)OCC)C=C3N(C(CNCC)=O)C=2C=CC=1"
bupropion (S- and R-),10.1124/dmd.116.072363 ,"C1=CC=C(Cl)C=C1C(=O)[C@@H](NC(C)(C)C)C","C1=CC(O)=C(Cl)C=C1C(=O)[C@@H](NC(C)(C)C)C" "C1=CC=C(Cl)C=C1[C@@H0](O)1[C@H](C)NC(C)(C)CO1"
imipramine,10.1124/dmd.116.071639 ,"C1C2CCC3=CC=CC=C3N(CCCN(C)C)C=2C=CC=1","C1C2CCC3=CC(O)=CC=C3N(CCCN(C)C)C=2C=CC=1" "C1C2CCC3=CC=CC=C3N(CCCNC)C=2C=CC=1"
lapatinib,10.1124/dmd.116.070839 ,"C1=CC(C2=CC=C(CNCCS(C)(=O)=O)O2)=CC2C(NC3=CC(Cl)=C(OCC4=CC(F)=CC=C4)C=C3)=NC=NC1=2","C1=CC(C2=CC=C(CN(O)CCS(C)(=O)=O)O2)=CC2C(NC3=CC(Cl)=C(OCC4=CC(F)=CC=C4)C=C3)=NC=NC1=2" "C1=CC(C2=CC=C(CN)O2)=CC2C(NC3=CC(Cl)=C(OCC4=CC(F)=CC=C4)C=C3)=NC=NC1=2" "C1=CC(C2=CC=C(CNCCS(=O)(C)=O)O2)=CC2C(NC3=CC(Cl)=C(O)C=C3)=NC=NC1=2"
dasabuvir,10.1124/dmd.115.067512 ,"C1=C(N2C(=O)NC(=O)C=C2)C=C(C(C)(C)C)C(OC)=C1C1=CC2C=CC(NS(=O)(=O)C)=CC=2C=C1","C1=C(N2C(=O)NC(=O)C=C2)C=C(C(C)(C)CO)C(OC)=C1C1=CC2C=CC(NS(=O)(=O)C)=CC=2C=C1"
atomoxetine,10.1124/dmd.116.069518 ,"C1=CC=CC=C1[C@@H](CCNC)OC1=C(C)C=CC=C1","C1=CC=CC=C1[C@@H](CCN)OC1=C(C)C=CC=C1" "C1=CC=CC=C1[C@@H](CCNC)OC1=C(C)C=C(O)C=C1" "C1=CC=CC=C1[C@@H](CCNC)OC1=C(CO)C=CC=C1"
turinabol,10.1124/dmd.115.066829 ,"C1=CC(=O)C(Cl)=C2CC[C@@H0]([HH0])3[C@H0]([HH0])4CC[C@H0](C)(O)[C@H0]4(C)CC[C@@H0]3([HH0])[C@@H0]12C","C1=CC(=O)C(Cl)=C2CC[C@@H0]([HH0])3[C@H0]([HH0])4CC[C@H0](C)(O)[C@H0]4(C)C[C@H](O)[C@@H0]3([HH0])[C@@H0]12C"
axitinib,10.1124/dmd.115.065615 ,"C1=CC=CN=C1/C=C/C1C2C=CC(SC3=CC=CC=C3C(=O)NC)=CC=2NN=1","C1=CC=CN=C1/C=C/C1C2C=CC(S(=O)C3=CC=CC=C3C(=O)NC)=CC=2NN=1" "C1=CC=C[NH0+]([OH0-])=C1/C=C/C1C2C=CC(SC3=CC=CC=C3C(=O)NC)=CC=2NN=1" "C1=CC=CN=C1/C=C/C1C2C=CC(SC3=CC=CC=C3C(=O)NCO)=CC=2NN=1" "C1=CC=CN=C1C1OC1C1C2C=CC(SC3=CC=CC=C3C(=O)NC)=CC=2NN=1"
bosentan,10.1124/dmd.115.067074 ,"C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=NC(C2=NC=CC=N2)=NC(OCCO)=C1OC1=CC=CC=C1OC","C1=CC(C(C)(C)C)=CC=C1S(=O)(=O)NC1=NC(C2=NC=CC=N2)=NC(OCCO)=C1OC1=CC=CC=C1O" "C1=CC(C(C)(C)CO)=CC=C1S(=O)(=O)NC1=NC(C2=NC=CC=N2)=NC(OCCO)=C1OC1=CC=CC=C1OC"
GDC-0623,10.1124/dmd.115.067181 ,"C(C(=O)NOCCO)1C=CC2=CN=CN2C=1NC1=CC=C(I)C=C1F","C(C(=O)N)1C=CC2=CN=CN2C=1NC1=CC=C(I)C=C1F" "C12C(=O)NN(C3=CC=C(I)C=C3F)C=1N1C=NC=C1C=C2"
montelukast,10.1124/dmd.115.065763 ,"C1=CC(Cl)=CC2N=C(/C=C/C3=CC=CC([C@H](SCC4(CC4)C(O)=O)CCC4=C(C(C)(C)O)C=CC=C4)=C3)C=CC1=2","C1=CC(Cl)=CC2N=C(/C=C/C3=CC=CC([C@H](SCC4(CC4)C(O)=O)CCC4=C(C(C)(C)O)C=C(O)C=C4)=C3)C=CC1=2" "C1=CC(Cl)=CC2N=C(/C=C/C3=CC=CC([C@H](SCC4(CC4)C(O)=O)CCC4=C(C(CO)(C)O)C=CC=C4)=C3)C=CC1=2" "C1=CC(Cl)=CC2N=C(/C=C/C3=CC=CC([C@H](S(=O)CC4(CC4)C(O)=O)CCC4=C(C(C)(C)O)C=CC=C4)=C3)C=CC1=2" "C1=CC(Cl)=CC2N=C(/C=C/C3=CC=CC([C@H](SCC4(CC4)C(O)=O)CC(O)C4=C(C(C)(C)O)C=CC=C4)=C3)C=CC1=2"
olanzapine,10.1124/dmd.115.064790 ,"C1=CC=CC2N=C(N3CCN(C)CC3)C3C=C(C)SC=3NC1=2","C1=CC=CC2N=C(N3CCNCC3)C3C=C(C)SC=3NC1=2" "C1=CC(O)=CC2N=C(N3CCN(C)CC3)C3C=C(C)SC=3NC1=2" "C1=CC=CC2N=C(N3CCN(C)CC3)C3C=C(CO)SC=3NC1=2" "N1C2SC(C)=CC=2C(N2CC[NH0+](C)([OH0-])CC2)=NC2C=CC=CC1=2"
benzbromarone,10.1124/dmd.115.065037 ,"C1=CC=CC2C(C(C3=CC(Br)=C(O)C(Br)=C3)=O)C(CC)OC1=2","C1=CC=CC2C(C(C3=CC(Br)=C(O)C(O)=C3)=O)C(CC)OC1=2" "C1=C(O)C=CC2C(C(C3=CC(Br)=C(O)C(Br)=C3)=O)C(CC)OC1=2" "OC1=CC(Br)=C(O)C(Br)=C1"
trimethoprim,10.1124/dmd.115.065193 ,"C1=NC(N)=NC(N)=C1CC1=CC(OC)=C(OC)C(OC)=C1","C1=NC(N)=NC(N)=C1C(O)C1=CC(OC)=C(OC)C(OC)=C1" "C1=NC(N)=NC(N)=C1CC1=CC(OC)=C(O)C(OC)=C1" "C1=NC(N)=NC(N)=C1CC1=CC(OC)=C(OC)C(O)=C1" "C1=NC(N)=[NH0+]([OH0-])C(N)=C1CC1=CC(OC)=C(OC)C(OC)=C1" "C1=[NH0+]([OH0-])C(N)=NC(N)=C1CC1=CC(OC)=C(OC)C(OC)=C1"
ifosfamide,10.1124/dmd.115.063628 ,"N(CCCl)1P(=O)(NCCCl)OCCC1","N(CCCl)1P(=O)(N)OCCC1" "N(CCCl)1P(=O)(NCCCl)OCCC1O" "N1P(=O)(NCCCl)OCCC1" "ClCC=O"
lenvatinib,10.1124/dmd.114.058073 ,"C1=C(OC)C(C(=O)N)=CC2C(OC3=CC=C(NC(=O)NC4CC4)C(Cl)=C3)=CC=NC1=2","C1=C(O)C(C(=O)N)=CC2C(OC3=CC=C(NC(=O)NC4CC4)C(Cl)=C3)=CC=NC1=2" "C1=C(OC)C(C(=O)N)=CC2C(OC3=CC=C(NC(=O)NC4CC4)C(Cl)=C3)=CC=[NH0+]([OH0-])C1=2"
evodiamine,10.1124/dmd.114.057414 ,"C1=CC=CC2NC3C4N(C)C5C=CC=CC=5C(=O)N4CCC=3C1=2","C1=C(O)C=CC2NC3C4N(C)C5C=CC=CC=5C(=O)N4CCC=3C1=2" "C1=CC=CC2NC3C4N(C)C5C=CC=CC=5C(=O)N4CC(O)C=3C1=2"
ticlopidine,10.1124/dmd.113.053017 ,"C1=CSC2CCN(CC3=C(Cl)C=CC=C3)CC1=2","C1C(=O)SC2CCN(CC3=C(Cl)C=CC=C3)CC=12"