CDK 0807181207 4 3 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 M END > InChI=1S/C2H4Cl2/c3-1-2-4/h1-2H2 > 1,2-dichloroethane > M01 M02 > M01 NAME: S-(2-chloroethyl)glutathione PUBCHEM_CID: NULL INCHI: InChI=1S/C12H20ClN3O6S/c13-3-4-23-6-8(11(20)15-5-10(18)19)16-9(17)2-1-7(14)12(21)22/h7-8H,1-6,14H2,(H,15,20)(H,16,17)(H,18,19)(H,21,22) M02 NAME: 1,2-dichloroethanol PUBCHEM_CID: NULL INCHI: InChI=1S/C2H4Cl2O/c3-1-2(4)5/h2,5H,1H2 > 7.19. Halogenated Hydrocarbons; H M Mehendale $$$$ CDK 0807181207 11 12 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6 4 1 0 0 0 0 7 5 1 0 0 0 0 8 1 1 0 0 0 0 8 2 1 0 0 0 0 9 3 1 0 0 0 0 9 4 1 0 0 0 0 9 5 1 0 0 0 0 10 6 1 0 0 0 0 10 7 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 11 10 1 0 0 0 0 M END > InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3 > 1,4-Cineole > M01 M02 M03 > M01 NAME: 1-Methyl-1-[1-methyl-7-oxabicyclo[2.2.1]heptane-4-yl]ethanol PUBCHEM_CID: 14191736 INCHI: InChI=1S/C10H18O2/c1-8(2,11)10-6-4-9(3,12-10)5-7-10/h11H,4-7H2,1-3H3 M02 NAME: 1,4-Epoxy-p-menthane-2-ol PUBCHEM_CID: 113623 INCHI: InChI=1S/C10H18O2/c1-7(2)10-5-4-9(3,12-10)8(11)6-10/h7-8,11H,4-6H2,1-3H3 M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C10H18O2/c1-8(7-11)10-5-3-9(2,12-10)4-6-10/h8,11H,3-7H2,1-2H3 > Walter Jäger and Martina Höferl; Metabolism of Terpenoids in Animal Models and Humans; p. 265; in Handbook of Essential Oils: Science, Technology, and Applications $$$$ CDK 0807181207 21 24 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 4 1 1 0 0 0 0 5 2 1 0 0 0 0 6 3 2 0 0 0 0 7 3 1 0 0 0 0 9 8 2 0 0 0 0 10 4 2 0 0 0 0 11 8 1 0 0 0 0 11 10 1 0 0 0 0 12 5 2 0 0 0 0 12 10 1 0 0 0 0 13 6 1 0 0 0 0 14 7 2 0 0 0 0 15 9 1 0 0 0 0 15 13 2 0 0 0 0 16 11 2 0 0 0 0 16 13 1 0 0 0 0 16 14 1 0 0 0 0 17 12 1 0 0 0 0 17 14 1 0 0 0 0 18 15 1 0 0 0 0 19 17 2 0 0 0 0 20 18 2 0 0 0 0 21 18 2 0 0 0 0 M END > InChI=1S/C17H9NO3/c19-17-12-5-2-1-4-10(12)11-8-9-15(18(20)21)13-6-3-7-14(17)16(11)13/h1-9H > 3-Nitrobenzanthrone > M01 > M01 NAME: N-hydroxy-3-aminobenzanthrone PUBCHEM_CID: 24849078 INCHI: InChI=1S/C17H11NO2/c19-17-12-5-2-1-4-10(12)11-8-9-15(18-20)13-6-3-7-14(17)16(11)13/h1-9,18,20H > Arlt, VM. et al. (2004); 3-Aminobenzanthrone, a Human Metabolite of the Environmental Pollutant 3-Nitrobenzanthrone, Forms DNA Adducts after Metabolic Activation by Human and Rat Liver Microsomes: Evidence for Activation by Cytochrome P450 1A1 and P450 1A2; Chem. Res. Toxicol., 17, 1092-1101 $$$$ CDK 0807181207 12 12 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 5 1 1 0 0 0 0 5 3 2 0 0 0 0 5 4 1 0 0 0 0 6 2 1 0 0 0 0 7 3 1 0 0 0 0 7 6 2 0 0 0 0 8 4 1 0 0 0 0 9 6 1 0 0 0 0 10 7 1 0 0 0 0 11 8 2 0 0 0 0 12 8 1 0 0 0 0 M END > InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) > 3,4-dihydroxyphenylacetic acid > M01 M02 M03 M04 > M01 NAME: Homovanillic acid PUBCHEM_CID: 1738 INCHI: InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12) M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C8H8O7S/c9-6-2-1-5(4-8(10)11)3-7(6)15-16(12,13)14/h1-3,9H,4H2,(H,10,11)(H,12,13,14) M03 NAME: 3,4-DIHYDROXYBENZOIC ACID PUBCHEM_CID: 72 INCHI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11) M04 NAME: 3-Hydroxyphenylacetic acid PUBCHEM_CID: 12122 INCHI: InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) M05 NAME: 4-Hydroxyphenylacetic acid PUBCHEM_CID: NULL INCHI: InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11) > Serra, A. et al. (2012); Metabolic pathways of the colonic metabolism of flavonoids (flavonols, flavones and flavanones) and phenolic acids; Food Chemistry 130 (2012) 383–393; PMCID:PMC3798909; DOI: 10.3390/nu5093367 $$$$ CDK 0807181207 25 29 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3 2 1 0 0 0 0 5 4 2 0 0 0 0 7 2 1 0 0 0 0 8 4 1 0 0 0 0 9 3 1 0 0 0 0 10 6 2 0 0 0 0 11 6 1 0 0 0 0 12 7 2 0 0 0 0 12 9 1 0 0 0 0 13 7 1 0 0 0 0 13 10 1 0 0 0 0 14 8 1 0 0 0 0 14 11 2 0 0 0 0 15 13 2 0 0 0 0 15 14 1 0 0 0 0 16 12 1 0 0 0 0 17 8 1 0 0 0 0 18 9 2 0 0 0 0 19 16 2 0 0 0 0 20 1 1 0 0 0 0 20 10 1 0 0 0 0 21 5 1 0 0 0 0 21 17 1 0 0 0 0 22 11 1 0 0 0 0 22 17 1 0 0 0 0 23 15 1 0 0 0 0 23 16 1 0 0 0 0 24 8 1 0 0 0 0 25 17 1 0 0 0 0 M END > InChI=1S/C17H12O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8,17H,2-3H2,1H3/t8-,17+/m0/s1 > Aflatoxin B1 > M01 M02 M03 M04 M05 > M01 NAME: Aflatoxin Q1 PUBCHEM_CID: NULL INCHI: InChI=1S/C17H12O7/c1-21-9-5-10-11(6-2-3-22-17(6)23-10)15-14(9)12-7(18)4-8(19)13(12)16(20)24-15/h2-3,5-7,17-18H,4H2,1H3/t6-,7?,17+/m0/s1 M02 NAME: AFB1- 8,9-epoxide PUBCHEM_CID: NULL INCHI: InChI=1S/C17H12O7/c1-20-7-4-8-11(12-14-17(23-14)24-16(12)21-8)13-10(7)5-2-3-6(18)9(5)15(19)22-13/h4,12,14,16-17H,2-3H2,1H3/t12-,14?,16+,17?/m1/s1 M03 NAME: Aflatoxin P1 PUBCHEM_CID: NULL INCHI: InChI=1S/C16H10O6/c17-8-2-1-6-11-9(18)5-10-13(7-3-4-20-16(7)21-10)14(11)22-15(19)12(6)8/h3-5,7,16,18H,1-2H2/t7-,16+/m0/s1 M04 NAME: Aflatoxicol (AFL) PUBCHEM_CID: NULL INCHI: InChI=1S/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h4-6,8-9,17-18H,2-3H2,1H3/t8-,9?,17+/m0/s1 M05 NAME: Aflatoxin M1 PUBCHEM_CID: NULL INCHI: InChI=1S/C17H12O7/c1-21-9-6-10-13(17(20)4-5-22-16(17)23-10)14-12(9)7-2-3-8(18)11(7)15(19)24-14/h4-6,16,20H,2-3H2,1H3/t16-,17?/m1/s1 M06 NAME: Aflatoxin B2 PUBCHEM_CID: NULL INCHI: InChI=1/C17H14O6/c1-20-10-6-11-14(8-4-5-21-17(8)22-11)15-13(10)7-2-3-9(18)12(7)16(19)23-15/h6,8,17H,2-5H2,1H3 > Metabolism of aflatoxins: key enzymes and interindividual as well as interspecies differences Aflatoxins metabolism, effects on epigenetic mechanisms and their role in carcinogenesis 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 $$$$ CDK 0807181207 20 24 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 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 5 3 2 0 0 0 0 6 3 1 0 0 0 0 7 2 1 0 0 0 0 9 8 2 0 0 0 0 11 10 2 0 0 0 0 13 5 1 0 0 0 0 13 8 1 0 0 0 0 14 6 2 0 0 0 0 14 10 1 0 0 0 0 15 4 2 0 0 0 0 15 12 1 0 0 0 0 16 9 1 0 0 0 0 16 12 2 0 0 0 0 17 7 2 0 0 0 0 17 15 1 0 0 0 0 18 11 1 0 0 0 0 18 17 1 0 0 0 0 19 13 2 0 0 0 0 19 14 1 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 M END > InChI=1S/C20H12/c1-2-7-17-15(4-1)12-16-9-8-13-5-3-6-14-10-11-18(17)20(16)19(13)14/h1-12H > Benzo[a]pyrene > M01 M02 M03 > M01 NAME: Benzo[a]pyrene-9,10-oxide PUBCHEM_CID: 37456 INCHI: InChI=1S/C20H12O/c1-2-11-4-5-13-10-14-7-9-16-20(21-16)19(14)15-8-6-12(3-1)17(11)18(13)15/h1-10,16,20H M02 NAME: Benzo(a)pyrene 7,8-epoxide PUBCHEM_CID: 37455 INCHI: InChI=1S/C20H12O/c1-2-11-4-5-13-10-16-14(8-9-17-20(16)21-17)15-7-6-12(3-1)18(11)19(13)15/h1-10,17,20H M03 NAME: Benzo(a)pyrene 2,3-epoxide PUBCHEM_CID: NULL INCHI: InChI=1S/C20H12O/c1-2-4-14-11(3-1)9-12-6-8-16-19-13(10-17-20(16)21-17)5-7-15(14)18(12)19/h1-10,17,20H M04 NAME: Benzo(a)pyrene 4,5-epoxide PUBCHEM_CID: 37786 INCHI: InChI=1/C20H12O/c1-2-6-13-12(4-1)10-16-18-14(13)9-8-11-5-3-7-15(17(11)18)19-20(16)21-19/h1-10,19-20H > 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 Shimada, T. et al. (2006); Xenobiotic-metabolizing enzymes involved in activation and detoxification of carcinogenic polycyclic aromatic hydrocarbons; Drug Metab Pharmacokinet.; 21(4):257-76; PMID:16946553 $$$$ CDK 0807181207 13 14 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6 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 8 7 1 0 0 0 0 9 5 1 0 0 0 0 9 7 1 0 0 0 0 10 4 1 0 0 0 0 10 5 1 0 0 0 0 10 6 1 0 0 0 0 10 8 1 0 0 0 0 11 9 2 0 0 0 0 12 7 1 0 0 0 0 13 8 1 0 0 0 0 M END > InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8-,10+/m1/s1 > beta-Thujone > M01 M02 M03 M04 M05 M06 > M01 NAME: 7-Hydroxy-beta-Thujone PUBCHEM_CID: 101118193 INCHI: InChI=1S/C10H16O2/c1-6-7-4-10(7,5-8(6)11)9(2,3)12/h6-7,12H,4-5H2,1-3H3/t6?,7?,10-/m1/s1 M02 NAME: 4-Hydroxy-beta-Thujone PUBCHEM_CID: NULL INCHI: InChI=1S/C10H16O2/c1-6(2)10-4-7(10)9(3,12)8(11)5-10/h6-7,12H,4-5H2,1-3H3/t7?,9?,10-/m0/s1 M03 NAME: 8-Hydroxy-beta-Thujone PUBCHEM_CID: NULL INCHI: InChI=1S/C10H16O2/c1-6(5-11)10-3-8(10)7(2)9(12)4-10/h6-8,11H,3-5H2,1-2H3/t6?,7?,8?,10-/m0/s1 M04 NAME: 10-Hydroxy-beta-Thujone PUBCHEM_CID: NULL INCHI: InChI=1S/C10H16O2/c1-6(2)10-3-8(10)7(5-11)9(12)4-10/h6-8,11H,3-5H2,1-2H3/t7?,8?,10-/m0/s1 M05 NAME: 7,8-dehydro-beta-Thujone PUBCHEM_CID: NULL INCHI: InChI=1S/C10H14O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h7-8H,1,4-5H2,2-3H3/t7?,8?,10-/m0/s1 M06 NAME: 2-Hydroxy-beta-Thujone PUBCHEM_CID: NULL INCHI: InChI=1S/C10H16O2/c1-5(2)10-4-7(10)6(3)8(11)9(10)12/h5-7,9,12H,4H2,1-3H3/t6?,7?,9?,10-/m0/s1 M07 NAME: Thujol PUBCHEM_CID: NULL INCHI: InChI=1S/C10H18O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-9,11H,4-5H2,1-3H3/t7-,8+,9?,10-/m0/s1 M08 NAME: 2-Cyclohexen-1-one, 2-methyl-5-(1-methylethyl)-, (S)- PUBCHEM_CID: 6432475 INCHI: InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,7,9H,5-6H2,1-3H3/t9-/m0/s1 > 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 0807181207 15 15 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3 1 2 0 0 0 0 2 4 2 0 0 0 0 6 1 1 0 0 0 0 6 2 1 0 0 0 0 6 5 2 0 0 0 0 7 3 1 0 0 0 0 8 5 1 0 0 0 0 8 7 2 0 0 0 0 9 4 1 0 0 0 0 10 7 1 0 0 0 0 11 8 1 0 0 0 0 12 9 2 0 0 0 0 13 9 1 0 0 0 0 14 2 1 0 0 0 0 15 4 1 0 0 0 0 M END > InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+ > Caffeic acid > M01 M02 M03 M04 M05 M06 M07 M08 M09 M10 > M01 NAME: Dihydrocaffeic acid PUBCHEM_CID: 348154 INCHI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13) M02 NAME: ferulic acid PUBCHEM_CID: 445858 INCHI: InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ M03 NAME: Isoferulic acid PUBCHEM_CID: 736186 INCHI: InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C15H16O10/c16-7-3-1-6(2-4-9(17)18)5-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+ M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C15H16O10/c16-7-5-6(2-4-9(17)18)1-3-8(7)24-15-12(21)10(19)11(20)13(25-15)14(22)23/h1-5,10-13,15-16,19-21H,(H,17,18)(H,22,23)/b4-2+ M06 NAME: caffeic acid 3-sulfate PUBCHEM_CID: 2261219 INCHI: InChI=1S/C9H8O7S/c10-7-3-1-6(2-4-9(11)12)5-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+ M07 NAME: Caffeic acid 4-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+ M08 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) M09 NAME: 4-Vinylbenzene-1,2-diol PUBCHEM_CID: 151398 INCHI: InChI=1S/C8H8O2/c1-2-6-3-4-7(9)8(10)5-6/h2-5,9-10H,1H2 M10 NAME: 3-Hydroxycinnamic acid PUBCHEM_CID: 637541 INCHI: InChI=1S/C9H8O3/c10-8-3-1-2-7(6-8)4-5-9(11)12/h1-6,10H,(H,11,12)/b5-4+ M11 NAME: caffeic acid 4-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C9H8O7S/c10-7-5-6(2-4-9(11)12)1-3-8(7)16-17(13,14)15/h1-5,10H,(H,11,12)(H,13,14,15)/b4-2+ > Stalmach, A. et al. (2009); Metabolite profiling of hydroxycinnamate derivatives in plasma and urine after the ingestion of coffee by humans: identification of biomarkers of coffee consumption; Drug Metab Dispos.;37(8):1749-58; PMID:19460943; DOI:10.1124/dmd.109.028019 Rechner, AR. (2003); Flavonoids in Health and Disease, Second Edition; ISBN 9780824742348; Chapter 17 Hu, H. et al. (2015); An organic solvent-tolerant phenolic acid decarboxylase from Bacillus licheniformis for the efficient bioconversion of hydroxycinnamic acids to vinyl phenol derivatives; Appl Microbiol Biotechnol.;99(12):5071-81. DOI:10.1007/s00253-014-6313-3; PMID:25547838 Wong, CC. et al. (2010); In vitro and in vivo conjugation of dietary hydroxycinnamic acids by UDP-glucuronosyltransferases and sulfotransferases in humans; J Nutr Biochem.;21(11):1060-8. DOI:10.1016/j.jnutbio.2009.09.001 $$$$ CDK 0807181207 11 11 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5 4 2 0 0 0 0 7 1 1 0 0 0 0 7 2 1 0 0 0 0 8 3 1 0 0 0 0 8 4 1 0 0 0 0 9 5 1 0 0 0 0 9 6 2 0 0 0 0 9 7 1 0 0 0 0 10 6 1 0 0 0 0 10 8 2 0 0 0 0 11 10 1 0 0 0 0 M END > InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4-7,11H,1-3H3 > Carvacrol > M01 M02 M03 M04 M05 M06 > M01 NAME: Carvacrol O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C16H22O7/c1-7(2)9-5-4-8(3)10(6-9)22-16-13(19)11(17)12(18)14(23-16)15(20)21/h4-7,11-14,16-19H,1-3H3,(H,20,21) M02 NAME: Carvacrol O-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C10H14O4S/c1-7(2)9-5-4-8(3)10(6-9)14-15(11,12)13/h4-7H,1-3H3,(H,11,12,13) M03 NAME: 8-hydroxycarvacrol (p-Cymene-2,8-diol) PUBCHEM_CID: 342518 INCHI: InChI=1S/C10H14O2/c1-7-4-5-8(6-9(7)11)10(2,3)12/h4-6,11-12H,1-3H3 M04 NAME: 8-hydroxycarvacrol PUBCHEM_CID: 84652415 INCHI: InChI=1S/C10H14O2/c1-7(2)8-3-4-9(6-11)10(12)5-8/h3-5,7,11-12H,6H2,1-2H3 M05 NAME: 2-hydroxycarvacrol PUBCHEM_CID: 95873 INCHI: InChI=1S/C10H14O2/c1-6(2)8-5-4-7(3)9(11)10(8)12/h4-6,11-12H,1-3H3 M06 NAME: 9-hydroxycarvacrol PUBCHEM_CID: 117276423 INCHI: InChI=1S/C10H14O2/c1-7-3-4-9(5-10(7)12)8(2)6-11/h3-5,8,11-12H,6H2,1-2H3 > Walter Jäger and Martina Höferl; Metabolism of Terpenoids in Animal Models and Humans; p. 265; in Handbook of Essential Oils: Science, Technology, and Applications $$$$ CDK 0807181207 44 43 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 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 8 6 1 0 0 0 0 9 7 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 12 10 1 0 0 0 0 13 11 1 0 0 0 0 14 12 1 0 0 0 0 15 13 1 0 0 0 0 16 14 1 0 0 0 0 17 15 1 0 0 0 0 18 17 1 0 0 0 0 19 16 1 0 0 0 0 20 18 1 0 0 0 0 21 19 1 0 0 0 0 22 20 1 0 0 0 0 23 21 1 0 0 0 0 24 22 1 0 0 0 0 25 23 1 0 0 0 0 26 24 1 0 0 0 0 27 25 1 0 0 0 0 28 26 1 0 0 0 0 29 27 1 0 0 0 0 30 28 1 0 0 0 0 29 31 2 0 0 0 0 32 30 1 0 0 0 0 34 33 1 0 0 0 0 35 31 1 0 0 0 0 35 34 1 0 0 0 0 36 32 1 0 0 0 0 37 34 1 0 0 0 0 37 36 2 0 0 0 0 38 33 1 0 0 0 0 39 35 1 0 0 0 0 40 36 1 0 0 0 0 41 29 1 0 0 0 0 42 31 1 0 0 0 0 43 34 1 0 0 0 0 44 35 1 0 0 0 0 M END > InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1 > Ceramide (d18:1/18:0) > > M01 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C18H38NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16H2,1,19H3/b15-14+ M02 NAME: COENZYME A,S-OCTADECANOATE PUBCHEM_CID: 1106 INCHI: InChI=1S/C39H70N7O17P3S/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/h26-28,32-34,38,49-50H,4-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54) M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+ M04 NAME: CerP(d18:1/18:0) PUBCHEM_CID: NULL INCHI: InChI=1S/C36H72NO6P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(39)37-34(33-43-44(40,41)42)35(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38H,3-28,30,32-33H2,1-2H3,(H,37,39)(H2,40,41,42)/b31-29+ M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C41H82N2O3/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-46-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3/p+1/b34-32+ M06 NAME: (2S,3R)-Sphingosine PUBCHEM_CID: 5353955 INCHI: InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+ M07 NAME: stearic acid PUBCHEM_CID: 5281 INCHI: InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20) M08 NAME: β-D-galactosyl-N-acylsphingosine, d18:1 PUBCHEM_CID: NULL INCHI: InChI=1S/C42H81NO8/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-38(46)43-35(34-50-42-41(49)40(48)39(47)37(33-44)51-42)36(45)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,35-37,39-42,44-45,47-49H,3-28,30,32-34H2,1-2H3,(H,43,46)/b31-29+/t35-,36+,37+,39-,40-,41+,42+/m0/s1 > Sphingolipid Metabolic Pathway- An Overview of Major Roles Played in Human Diseases http://www.genome.jp/kegg-bin/show_pathway?hsa00600 http://smpdb.ca/view/SMP00034# Jewison T et al. (2013); SMPDB 2.0: big improvements to the Small Molecule Pathway Database.; Nucleic Acids Res. 2014 Jan;42(Database issue):D478-84. doi: 10.1093/nar/gkt1067; PMID: 24203708 $$$$ CDK 0807181207 44 43 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 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 8 6 1 0 0 0 0 9 7 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 12 10 1 0 0 0 0 13 11 1 0 0 0 0 14 12 1 0 0 0 0 15 13 1 0 0 0 0 16 14 1 0 0 0 0 17 15 1 0 0 0 0 18 17 1 0 0 0 0 19 16 1 0 0 0 0 20 18 1 0 0 0 0 21 19 1 0 0 0 0 22 20 1 0 0 0 0 23 21 1 0 0 0 0 24 22 1 0 0 0 0 25 23 1 0 0 0 0 26 24 1 0 0 0 0 27 25 1 0 0 0 0 28 26 1 0 0 0 0 29 27 1 0 0 0 0 30 28 1 0 0 0 0 29 31 2 0 0 0 0 32 30 1 0 0 0 0 34 33 1 0 0 0 0 35 31 1 0 0 0 0 35 34 1 0 0 0 0 36 32 1 0 0 0 0 37 34 1 0 0 0 0 37 36 2 0 0 0 0 38 33 1 0 0 0 0 39 35 1 0 0 0 0 40 36 1 0 0 0 0 41 29 1 0 0 0 0 42 31 1 0 0 0 0 43 34 1 0 0 0 0 44 35 1 0 0 0 0 M END > InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1 > Cholic acid > M01 M02 M03 M04 M05 M06 M07 M08 M09 M10 > M01 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C30H48O11/c1-13(4-7-21(33)34)16-5-6-17-22-18(12-20(32)30(16,17)3)29(2)9-8-15(10-14(29)11-19(22)31)40-28-25(37)23(35)24(36)26(41-28)27(38)39/h13-20,22-26,28,31-32,35-37H,4-12H2,1-3H3,(H,33,34)(H,38,39)/t13?,14?,15?,16?,17?,18?,19?,20?,22?,23?,24?,25?,26?,28?,29-,30+/m0/s1 M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C30H48O11/c1-13(4-7-21(33)34)16-5-6-17-22-18(12-20(32)30(16,17)3)29(2)9-8-15(31)10-14(29)11-19(22)40-28-25(37)23(35)24(36)26(41-28)27(38)39/h13-20,22-26,28,31-32,35-37H,4-12H2,1-3H3,(H,33,34)(H,38,39)/t13?,14?,15?,16?,17?,18?,19?,20?,22?,23?,24?,25?,26?,28?,29-,30+/m0/s1 M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C30H48O11/c1-13(4-7-21(34)40-28-25(37)23(35)24(36)26(41-28)27(38)39)16-5-6-17-22-18(12-20(33)30(16,17)3)29(2)9-8-15(31)10-14(29)11-19(22)32/h13-20,22-26,28,31-33,35-37H,4-12H2,1-3H3,(H,38,39)/t13?,14?,15?,16?,17?,18?,19?,20?,22?,23?,24?,25?,26?,28?,29-,30+/m0/s1 M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O8S/c1-13(4-7-21(27)28)16-5-6-17-22-18(12-20(26)24(16,17)3)23(2)9-8-15(32-33(29,30)31)10-14(23)11-19(22)25/h13-20,22,25-26H,4-12H2,1-3H3,(H,27,28)(H,29,30,31)/t13?,14?,15?,16?,17?,18?,19?,20?,22?,23-,24+/m0/s1 M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O8S/c1-13(4-7-21(27)28)16-5-6-17-22-18(12-20(26)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)32-33(29,30)31/h13-20,22,25-26H,4-12H2,1-3H3,(H,27,28)(H,29,30,31)/t13?,14?,15?,16?,17?,18?,19?,20?,22?,23-,24+/m0/s1 M06 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C45H74N7O20P3S/c1-23(26-7-8-27-34-28(18-31(55)45(26,27)5)44(4)12-10-25(53)16-24(44)17-29(34)54)6-9-33(57)76-15-14-47-32(56)11-13-48-41(60)38(59)43(2,3)20-69-75(66,67)72-74(64,65)68-19-30-37(71-73(61,62)63)36(58)42(70-30)52-22-51-35-39(46)49-21-50-40(35)52/h21-31,34,36-38,42,53-55,58-59H,6-20H2,1-5H3,(H,47,56)(H,48,60)(H,64,65)(H,66,67)(H2,46,49,50)(H2,61,62,63)/t23?,24?,25?,26?,27?,28?,29?,30?,31?,34?,36?,37?,38?,42?,44-,45+/m0/s1 M07 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h14-21,25-26H,4-13H2,1-3H3,(H,27,28)/t14?,15?,16?,17?,18?,19?,20?,21?,23-,24+/m0/s1 M08 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13?,14?,16?,17?,18?,19?,20?,22?,23-,24+/m0/s1 M09 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13?,14?,15?,16?,17?,18?,20?,22?,23-,24+/m0/s1 M10 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H40O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-20,22,25-27H,4-12H2,1-3H3,(H,28,29)/t13?,14?,15?,16?,17?,18?,19?,22?,23-,24+/m0/s1 > Chiang, JYL. (2017); Bile acid metabolism and signaling in liver disease and therapy; Liver Research; 1(2017) 3-9 Trottier, J. et al. (2013); Profiling serum bile acid glucuronides in humans: gender divergences, genetic determinants and response to fenofibrate; Clin Pharmacol Ther.; 94(4): 533–543. DOI:10.1038/clpt.2013.122. Alnouti, Y. et al. (108); Bile Acid Sulfation: A Pathway of Bile Acid Elimination and Detoxification; TOXICOLOGICAL SCIENCES 108(2), 225–246; DOI:10.1093/toxsci/kfn268 Falany, CN. et al. (1994); Glycine and taurine conjugation of bile acids by a single enzyme. Molecular cloning and expression of human liver bile acid CoA:amino acid N-acyltransferase; J Biol Chem.;269(30):19375-9; PMID:8034703 Macdonald, IA. et al. (1983); Degradation of steroids in the human gut; J Lipid Res.;24(6):675-700; PMID:6350517 Ridlon, JM. et al. (2006); Bile salt biotransformations by human intestinal bacteria; J Lipid Res.;47(2):241-59; PMID:16299351; DOI:10.1194/jlr.R500013-JLR200 $$$$ CDK 0807181207 31 32 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3 7 2 0 0 0 0 4 8 2 0 0 0 0 9 5 2 0 0 0 0 10 6 2 0 0 0 0 14 3 1 0 0 0 0 14 5 1 0 0 0 0 14 11 2 0 0 0 0 15 4 1 0 0 0 0 15 6 1 0 0 0 0 15 12 2 0 0 0 0 16 7 1 0 0 0 0 16 13 1 0 0 0 0 17 8 1 0 0 0 0 17 13 1 0 0 0 0 18 9 1 0 0 0 0 19 10 1 0 0 0 0 20 11 1 0 0 0 0 20 18 2 0 0 0 0 21 12 1 0 0 0 0 21 19 2 0 0 0 0 22 16 2 0 0 0 0 23 17 2 0 0 0 0 24 18 1 0 0 0 0 25 19 1 0 0 0 0 26 1 1 0 0 0 0 26 20 1 0 0 0 0 27 2 1 0 0 0 0 27 21 1 0 0 0 0 28 3 1 0 0 0 0 29 4 1 0 0 0 0 30 7 1 0 0 0 0 31 8 1 0 0 0 0 M END > InChI=1S/C21H20O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3-12,24-25H,13H2,1-2H3/b7-3+,8-4+ > Curcumin > M01 M02 M03 M04 M05 M06 M07 > M01 NAME: dihydrocurcumin PUBCHEM_CID: 10429233 INCHI: InChI=1S/C21H22O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(25)21(12-15)27-2/h3,5-7,9-12,24-25H,4,8,13H2,1-2H3/b7-3+ M02 NAME: Dehydrozingerone (Feruloylmethane) PUBCHEM_CID: 5354238 INCHI: InChI=1S/C11H12O3/c1-8(12)3-4-9-5-6-10(13)11(7-9)14-2/h3-7,13H,1-2H3/b4-3+ M03 NAME: ferulic acid PUBCHEM_CID: NULL INCHI: InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C27H28O12/c1-36-20-11-14(5-9-18(20)30)3-7-16(28)13-17(29)8-4-15-6-10-19(21(12-15)37-2)38-27-24(33)22(31)23(32)25(39-27)26(34)35/h3-12,22-25,27,30-33H,13H2,1-2H3,(H,34,35)/b7-3+,8-4+ M05 NAME: Curcumin sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C21H20O9S/c1-28-20-11-14(5-9-18(20)24)3-7-16(22)13-17(23)8-4-15-6-10-19(21(12-15)29-2)30-31(25,26)27/h3-12,24H,13H2,1-2H3,(H,25,26,27)/b7-3+,8-4+ M06 NAME: Mono-O-Demethylcurcumin PUBCHEM_CID: 5469426 INCHI: InChI=1S/C20H18O6/c1-26-20-11-14(5-9-18(20)24)3-7-16(22)12-15(21)6-2-13-4-8-17(23)19(25)10-13/h2-11,23-25H,12H2,1H3/b6-2+,7-3+ M07 NAME: PUBCHEM_CID: 89978543 INCHI: InChI=1S/C21H20O5/c1-25-19-5-3-4-15(12-19)6-9-17(22)14-18(23)10-7-16-8-11-20(24)21(13-16)26-2/h3-13,24H,14H2,1-2H3/b9-6+,10-7+ M08 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C8H8O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-5,10H,1H3 M09 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C13H14O4/c1-9(14)7-11(15)5-3-10-4-6-12(16)13(8-10)17-2/h3-6,8,16H,7H2,1-2H3/b5-3+ > Ireson, C.R. et al.; Metabolism of the Cancer Chemopreventive Agent Curcumin in Human and Rat Intestine; Cancer Epidemiology, Biomarkers & Prevention; Vol. 11, 105–111, January 2002 Wang YJ, Pan MH, Cheng AL, Lin LI, Ho YS, Hsieh CY, Lin JK. Stability of curcumin in buffer solutions and characterization of its degradation products. J. Pharm. Biomed. Anal. 1997;15:1867–76. Burapan, S. et al. (2017); Curcuminoid Demethylation as an Alternative Metabolism by Human Intestinal Microbiota; J Agric Food Chem.; 65(16):3305-3310. doi: 10.1021/acs.jafc.7b00943 Wang, K. and Qiu, F. (2013); Curcuminoid metabolism and its contribution to the pharmacological effects; Curr Drug Metab. 2013 Sep;14(7):791-806; PMID:23937173 Griesser, M. t al. (2011); Autoxidative and Cyclooxygenase-2 Catalyzed Transformation of the Dietary Chemopreventive Agent Curcumin; DOI:10.1074/jbc.M110.178806; PMCID:PMC3020718 $$$$ CDK 0807181207 21 23 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 7 1 1 0 0 0 0 7 3 2 0 0 0 0 8 4 1 0 0 0 0 8 5 2 0 0 0 0 9 6 2 0 0 0 0 10 2 1 0 0 0 0 11 4 2 0 0 0 0 11 9 1 0 0 0 0 12 3 1 0 0 0 0 12 10 2 0 0 0 0 13 6 1 0 0 0 0 14 5 1 0 0 0 0 14 9 1 0 0 0 0 15 7 1 0 0 0 0 15 13 2 0 0 0 0 16 8 1 0 0 0 0 17 10 1 0 0 0 0 18 11 1 0 0 0 0 19 12 1 0 0 0 0 20 13 1 0 0 0 0 21 14 2 0 0 0 0 21 15 1 0 0 0 0 M CHG 1 21 1 M END > InChI=1S/C15H10O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-6H,(H4-,16,17,18,19,20)/p+1 > Cyanidin > M01 M02 M03 M04 > M01 NAME: Peonidin PUBCHEM_CID: 441773 INCHI: InChI=1S/C16H12O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-7H,1H3,(H3-,17,18,19,20)/p+1 M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H18O12/c22-8-4-11(24)9-6-14(32-21-17(28)15(26)16(27)19(33-21)20(29)30)18(31-13(9)5-8)7-1-2-10(23)12(25)3-7/h1-6,15-17,19,21,26-28H,(H4-,22,23,24,25,29,30)/p+1 M03 NAME: 2,4,6-Trihydroxybenzaldehyde PUBCHEM_CID: 68099 INCHI: InChI=1S/C7H6O4/c8-3-5-6(10)1-4(9)2-7(5)11/h1-3,9-11H M04 NAME: 3,4-Dihydroxyphenylacetic acid PUBCHEM_CID: 547 INCHI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12) > Hanske, L. et al. (2013); Contribution of gut bacteria to the metabolism of cyanidin 3-glucoside in human microbiota-associated rats; British Journal of Nutrition (2013), 109, 1433–1441; doi:10.1017/S0007114512003376 $$$$ CDK 0807181207 19 21 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 1 1 0 0 0 0 4 2 2 0 0 0 0 6 5 2 0 0 0 0 9 1 2 0 0 0 0 9 2 1 0 0 0 0 10 3 2 0 0 0 0 10 4 1 0 0 0 0 11 5 1 0 0 0 0 11 7 2 0 0 0 0 12 6 1 0 0 0 0 13 8 2 0 0 0 0 13 9 1 0 0 0 0 14 7 1 0 0 0 0 14 12 2 0 0 0 0 15 12 1 0 0 0 0 15 13 1 0 0 0 0 16 10 1 0 0 0 0 17 11 1 0 0 0 0 18 15 2 0 0 0 0 19 8 1 0 0 0 0 19 14 1 0 0 0 0 M END > InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H > Daidzein > M01 M02 M03 M04 M05 M06 M07 > M01 NAME: DAIDZEIN 4'-BETA-D-GLUCURONIDE PUBCHEM_CID: 92024357 INCHI: InChI=1S/C21H18O10/c22-10-3-6-12-14(7-10)29-8-13(15(12)23)9-1-4-11(5-2-9)30-21-18(26)16(24)17(25)19(31-21)20(27)28/h1-8,16-19,21-22,24-26H,(H,27,28) M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H18O10/c22-10-3-1-9(2-4-10)13-8-29-14-7-11(5-6-12(14)15(13)23)30-21-18(26)16(24)17(25)19(31-21)20(27)28/h1-8,16-19,21-22,24-26H,(H,27,28) M03 NAME: Daidzein 4'-sulfate PUBCHEM_CID: 12114463 INCHI: InChI=1S/C15H10O7S/c16-10-3-6-12-14(7-10)21-8-13(15(12)17)9-1-4-11(5-2-9)22-23(18,19)20/h1-8,16H,(H,18,19,20) M04 NAME: Demethyltexasin PUBCHEM_CID: 5284649 INCHI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-14-6-13(18)12(17)5-10(14)15(11)19/h1-7,16-18H M05 NAME: 8-Hydroxydaidzein PUBCHEM_CID: 5466139 INCHI: InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-15-10(13(11)18)5-6-12(17)14(15)19/h1-7,16-17,19H M06 NAME: 3'-Hydroxydaidzein PUBCHEM_CID: 5284648 INCHI: InChI=1S/C15H10O5/c16-9-2-3-10-14(6-9)20-7-11(15(10)19)8-1-4-12(17)13(18)5-8/h1-7,16-18H M07 NAME: dihydrodaidzein PUBCHEM_CID: 176907 INCHI: InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2 M08 NAME: Daidzein 7-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C15H10O7S/c16-10-3-1-9(2-4-10)13-8-21-14-7-11(22-23(18,19)20)5-6-12(14)15(13)17/h1-8,16H,(H,18,19,20) > Kulling, SE. et al. (2001); Oxidative Metabolism of the Soy Isoflavones Daidzein and Genistein in Humans in Vitro and in Vivo; J. Agric. Food Chem. 2001, 49, 3024−3033 Shelnutt, SR. et al. (2002); Pharmacokinetics of the glucuronide and sulfate conjugates of genistein and daidzein in men and women after consumption of a soy beverage; Am J Clin Nutr.;76(3):588-94; PMID:12198004 Joannou, GE. et al. (1995); A urinary profile study of dietary phytoestrogens. The identification and mode of metabolism of new isoflavonoids; J Steroid Biochem Mol Biol.;54(3-4):167-84; PMID:7662591 $$$$ CDK 0807181207 23 25 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 7 1 1 0 0 0 0 7 3 2 0 0 0 0 8 4 2 0 0 0 0 8 5 1 0 0 0 0 9 6 1 0 0 0 0 10 2 1 0 0 0 0 11 4 1 0 0 0 0 11 9 2 0 0 0 0 12 3 1 0 0 0 0 12 10 2 0 0 0 0 13 6 1 0 0 0 0 14 5 2 0 0 0 0 14 9 1 0 0 0 0 15 7 1 0 0 0 0 15 13 1 0 0 0 0 16 8 1 0 0 0 0 17 10 1 0 0 0 0 18 11 1 0 0 0 0 19 12 1 0 0 0 0 20 13 1 0 0 0 0 21 14 1 0 0 0 0 21 15 1 0 0 0 0 22 13 1 0 0 0 0 23 15 1 0 0 0 0 M END > InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1 > Epicatechin > > M01 NAME: Arachidoside PUBCHEM_CID: 597207 INCHI: InChI=1S/C16H16O6/c1-21-15-4-8(2-3-11(15)18)16-13(20)7-10-12(19)5-9(17)6-14(10)22-16/h2-6,13,16-20H,7H2,1H3 M02 NAME: Epicatechin, 3-O-glucuronide PUBCHEM_CID: NULL INCHI: InChI=1S/C21H22O12/c22-8-4-11(24)9-6-12(25)18(31-13(9)5-8)7-1-2-10(23)14(3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30) M03 NAME: Epicatechin, 3-O-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C15H14O9S/c16-8-4-11(18)9-6-12(19)15(23-13(9)5-8)7-1-2-10(17)14(3-7)24-25(20,21)22/h1-5,12,15-19H,6H2,(H,20,21,22) M04 NAME: delta-(3,4-Dihydroxyphenyl)-gamma-valerolactone PUBCHEM_CID: 152432 INCHI: InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2 M05 NAME: phloroglucinol PUBCHEM_CID: NULL INCHI: InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H M06 NAME: 1,3,5-Benzenetriol, 2-[(2S)-3-(3,4-dihydroxyphenyl)-2-hydroxypropyl]- PUBCHEM_CID: 21722175 INCHI: InChI=1S/C15H16O6/c16-9(3-8-1-2-12(18)15(21)4-8)5-11-13(19)6-10(17)7-14(11)20/h1-2,4,6-7,9,16-21H,3,5H2 M07 NAME: 7-O-b-D-glucuronide-epicatechin PUBCHEM_CID: NULL INCHI: NULL M08 NAME: 7-O-sulfateepicatechin PUBCHEM_CID: NULL INCHI: NULL M09 NAME: 4'-O-sulfate-epicatechin PUBCHEM_CID: NULL INCHI: NULL M10 NAME: 5-O-sulfate-epicatechin PUBCHEM_CID: NULL INCHI: NULL M11 NAME: 5-O-b-D-glucuronide-epicatechin PUBCHEM_CID: NULL INCHI: NULL > Sanchez-Bridge, B. et al. (2015); Modulation of (-)-epicatechin metabolism by coadministration with other polyphenols in Caco-2 cell model; Drug Metab Dispos.;43(1):9-16; DOI:10.1124/dmd.114.060590; PMID:25315342 Laura Marín et al. (2014); Bioavailability of Dietary Polyphenols and Gut Microbiota Metabolism: Antimicrobial Properties Actis-Goretta, L. et al. (2013); Intestinal absorption, metabolism, and excretion of (–)-epicatechin in healthy humans assessed by using an intestinal perfusion technique; Am J Clin Nutr; 98:924–33 Borges, G. et al. (2017); Absorption, metabolism, distribution and excretion of (−)-epicatechin: A review of recent findings; DOI:10.1016/j.mam.2017.11.002; Molecular Aspects of Medicine); pp. 1-13 $$$$ CDK 0807181207 20 22 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 3 1 1 0 0 0 0 4 2 1 0 0 0 0 5 3 2 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 0 0 0 0 11 7 2 0 0 0 0 12 10 2 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 8 1 0 0 0 0 15 14 2 0 0 0 0 16 9 1 0 0 0 0 17 10 1 0 0 0 0 18 13 2 0 0 0 0 19 14 1 0 0 0 0 20 11 1 0 0 0 0 20 15 1 0 0 0 0 M END > InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H > Galangin > > M01 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H18O11/c22-9-6-10(23)12-11(7-9)30-17(8-4-2-1-3-5-8)18(13(12)24)31-21-16(27)14(25)15(26)19(32-21)20(28)29/h1-7,14-16,19,21-23,25-27H,(H,28,29) M02 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H18O11/c22-9-6-10-12(13(23)15(25)18(30-10)8-4-2-1-3-5-8)11(7-9)31-21-17(27)14(24)16(26)19(32-21)20(28)29/h1-7,14,16-17,19,21-22,24-27H,(H,28,29) M03 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C21H18O11/c22-10-6-9(30-21-17(27)14(24)16(26)19(32-21)20(28)29)7-11-12(10)13(23)15(25)18(31-11)8-4-2-1-3-5-8/h1-7,14,16-17,19,21-22,24-27H,(H,28,29) M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C15H10O8S/c16-10-6-9(23-24(19,20)21)7-11-12(10)13(17)14(18)15(22-11)8-4-2-1-3-5-8/h1-7,16,18H,(H,19,20,21) M05 NAME: kaempferol PUBCHEM_CID: 5280863 INCHI: InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H M06 NAME: 3,5,7-trihydroxy-2-phenyl-2,3-dihydrochromen-4-one PUBCHEM_CID: 3519897 INCHI: InChI=1S/C15H12O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,14-17,19H > Wu, B. et al. (2011); Regioselective Sulfation and Glucuronidation of Phenolics: Insights into the Structural Basis of Conjugation; Curr Drug Metab.;12(9):900-16; PMID:21933112; PMCID:PMC3426368 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 Labib, S. et al. (2006); Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds; Mol Nutr Food Res.;50(1):78-86; PMID:16317785; DOI:10.1002/mnfr.200500144 $$$$ CDK 0807181207 15 15 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 2 0 0 0 0 5 1 1 0 0 0 0 5 3 1 0 0 0 0 5 4 2 0 0 0 0 6 3 1 0 0 0 0 7 2 1 0 0 0 0 8 4 1 0 0 0 0 8 7 2 0 0 0 0 9 6 1 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 9 2 0 0 0 0 14 9 1 0 0 0 0 15 6 1 0 0 0 0 M END > InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1 > L-DOPA > > M01 NAME: dopamine PUBCHEM_CID: 681 INCHI: InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2 M02 NAME: PUBCHEM_CID: 18971002 INCHI: InChI=1S/CH2O2/c2-1-3/h1H,(H,2,3) M03 NAME: 2-amino-3-(4-hydroxy-3-methoxyphenyl)propanoic acid PUBCHEM_CID: 1670 INCHI: InChI=1S/C10H13NO4/c1-15-9-5-6(2-3-8(9)12)4-7(11)10(13)14/h2-3,5,7,12H,4,11H2,1H3,(H,13,14) M04 NAME: L-DOPA, 3-O-sulfate PUBCHEM_CID: NULL INCHI: InChI=1S/C9H11NO7S/c10-6(9(12)13)3-5-1-2-7(11)8(4-5)17-18(14,15)16/h1-2,4,6,11H,3,10H2,(H,12,13)(H,14,15,16) M05 NAME: DL-m-Tyrosine PUBCHEM_CID: 13052 INCHI: InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13) > Elroby, SAK. et al. (2012); Toward the Understanding of the Metabolism of Levodopa I. DFT Investigation of the Equilibrium Geometries, Acid-Base Properties and Levodopa-Water Complexes; Int. J. Mol. Sci. 2012, 13, 4321-4339; DOI:10.3390/ijms13044321 Kuchel, O. et al. (1990) Alternative catecholamine pathways after tyrosine hydroxylase inhibition in malignant pheochromocytoma. J Lab Clin Med.; 115(4):449-53 Sousa, T. et al. (2008); The gastrointestinal microbiota as a site for the biotransformation of drugs; Int J Pharm.;363(1-2):1-25; DOI: 10.1016/j.ijpharm.2008.07.009 $$$$ CDK 0807181207 12 12 0 0 0 0 0 0 0 0999 V2000 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 2 1 0 0 0 0 5 1 1 0 0 0 0 6 4 2 0 0 0 0 7 4 1 0 0 0 0 7 5 2 0 0 0 0 8 2 1 0 0 0 0 8 5 1 0 0 0 0 8 6 1 0 0 0 0 9 6 1 0 0 0 0 10 3 1 0 0 0 0 11 9 2 0 0 0 0 12 9 2 0 0 0 0 M END > InChI=1S/C6H9N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h4,10H,2-3H2,1H3 > Metronidazole > M01 M02 M03 M04 > M01 NAME: Metronidazole ?-D-Glucuronide PUBCHEM_CID: 85080190 INCHI: InChI=1S/C12H17N3O9/c1-5-13-4-6(15(21)22)14(5)2-3-23-12-9(18)7(16)8(17)10(24-12)11(19)20/h4,7-10,12,16-18H,2-3H2,1H3,(H,19,20) M02 NAME: 1-(2-hydroxyethyl)-2-hydroxymethyl-5-nitroimidazole PUBCHEM_CID: 121858 INCHI: InChI=1S/C6H9N3O4/c10-2-1-8-5(4-11)7-3-6(8)9(12)13/h3,10-11H,1-2,4H2 M03 NAME: (2-methyl-5-nitroimidazol-1-yl)-acetaldehyde PUBCHEM_CID: 11105771 INCHI: InChI=1S/C6H7N3O3/c1-5-7-4-6(9(11)12)8(5)2-3-10/h3-4H,2H2,1H3 M04 NAME: PUBCHEM_CID: 88854302 INCHI: InChI=1S/C6H9N3O2/c1-5-7-4-6(8-11)9(5)2-3-10/h4,10H,2-3H2,1H3 M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C4H7NO4/c6-2-1-5-3(7)4(8)9/h6H,1-2H2,(H,5,7)(H,8,9) M06 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) > Farrell, G. et al. (1984); Disposition and metabolism of metronidazole in patients with liver failure; Hepatology.;4(4):722-6; PMID:6745863 Koch, RL. and Goldman, P. (1979); The anaerobic metabolism of metronidazole forms N-(2-hydroxyethyl)-oxamic acid; J Pharmacol Exp Ther.;208(3):406-10. $$$$ CDK 0807181207 51 50 0 0 1 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6 1 1 0 0 0 0 7 2 1 0 0 0 0 8 6 1 0 0 0 0 9 7 1 0 0 0 0 10 8 1 0 0 0 0 11 9 1 0 0 0 0 12 10 1 0 0 0 0 13 11 1 0 0 0 0 14 12 1 0 0 0 0 15 13 1 0 0 0 0 16 14 1 0 0 0 0 17 15 1 0 0 0 0 18 16 1 0 0 0 0 19 17 1 0 0 0 0 20 18 1 0 0 0 0 21 19 1 0 0 0 0 22 20 1 0 0 0 0 23 21 1 0 0 0 0 24 22 1 0 0 0 0 25 23 1 0 0 0 0 26 24 1 0 0 0 0 27 25 1 0 0 0 0 28 26 1 0 0 0 0 29 27 1 0 0 0 0 30 28 1 0 0 0 0 31 29 1 0 0 0 0 32 30 1 0 0 0 0 33 31 1 0 0 0 0 35 34 1 0 0 0 0 38 36 1 0 0 0 0 38 37 1 0 0 0 0 39 32 1 0 0 0 0 40 33 1 0 0 0 0 41 3 1 0 0 0 0 41 4 1 0 0 0 0 41 5 1 0 0 0 0 41 34 1 0 0 0 0 42 39 2 0 0 0 0 43 40 2 0 0 0 0 46 36 1 0 0 0 0 46 39 1 0 0 0 0 47 35 1 0 0 0 0 48 37 1 0 0 0 0 49 38 1 0 0 0 0 49 40 1 0 0 0 0 50 44 2 0 0 0 0 50 45 1 0 0 0 0 50 47 1 0 0 0 0 50 48 1 0 0 0 0 51 38 1 0 0 0 0 M CHG 1 41 1 M CHG 1 45 -1 M END > InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1 > PC(16:0/16:0) > > M01 NAME: 1-Palmitoylglycerophosphocholine PUBCHEM_CID: 86555 INCHI: InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/p+1 M02 NAME: palmitic acid PUBCHEM_CID: 985 INCHI: InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18) M03 NAME: 5-Cholesten-3-acyl-palmitate PUBCHEM_CID: 4466036 INCHI: InChI=1S/C43H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h24,33-34,36-40H,7-23,25-32H2,1-6H3 M04 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C43H76O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-41(45)46-35-27-29-42(5)34(31-35)22-23-36-38-25-24-37(43(38,6)30-28-39(36)42)33(4)21-26-40(44)32(2)3/h22,32-33,35-40,44H,7-21,23-31H2,1-6H3 M05 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C45H80O2/c1-8-10-11-12-13-14-15-16-17-18-19-20-21-22-43(46)47-38-29-31-44(6)37(33-38)25-26-39-41-28-27-40(45(41,7)32-30-42(39)44)35(5)23-24-36(9-2)34(3)4/h25,34-36,38-42H,8-24,26-33H2,1-7H3 M06 NAME: 1,2-Dipalmitoyl-rac-glycero-3-phospho-L-serine PUBCHEM_CID: 181664 INCHI: InChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45) M07 NAME: choline PUBCHEM_CID: 305 INCHI: InChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1 M08 NAME: PUBCHEM_CID: NULL INCHI: InChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)32-23(21-26)22-31-33(28,29)30-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/p+1 M09 NAME: 1,2-Dipalmitoyl-rac-glycerophosphoric acid PUBCHEM_CID: 3099 INCHI: InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40) M10 NAME: Ethyltrimethylammonium PUBCHEM_CID: 33993 INCHI: InChI=1S/C5H14N/c1-5-6(2,3)4/h5H2,1-4H3/q+1 > http://www.genome.jp/kegg-bin/show_pathway?org_name=hsa&mapno=00564&mapscale=&show_description=hide PMID:12975367 PMID:661432 PMID:736674 PMID:662168 $$$$