Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0768)
Drug Name
BIO-300
Synonyms
Bonistein; Differenol A; Genestein; Genisteol; Genisterin; NPI 031L; Prunetol; SIPI 807-1; Sophoricol; genistein; 4',5, 7-Trihydroxyisoflavone; 4',5,7-Trihydroxyisoflavone; 4,5,7-Trihydroxyiso-flavone; 446-72-0; 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-; 5,7,4'-Trihydroxyisoflavone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one; C.I. 75610; CCRIS 7675; NSC 36586; UNII-DH2M523P0H
Indication Prostate cancer [ICD11: 2C82] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 270.24 Topological Polar Surface Area 87
Heavy Atom Count 20 Rotatable Bond Count 1
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
5280961
PubChem SID
8792 ; 93197 ; 606653 ; 640215 ; 854585 ; 854586 ; 3153130 ; 4652582 ; 7887819 ; 8138208 ; 8144401 ; 8616462 ; 10318994 ; 11111233 ; 11111234 ; 11113921 ; 11114608 ; 11120325 ; 11120813 ; 11121301 ; 11341576 ; 11361759 ; 11363214 ; 11364972 ; 11365776 ; 11367534 ; 11368338 ; 11370096 ; 11371695 ; 11373135 ; 11375144 ; 11375696 ; 11376500 ; 11378267 ; 11404364 ; 11407761 ; 11484372 ; 11487161 ; 11488454 ; 11490494 ; 11493357 ; 11494134 ; 15197341 ; 17389520 ; 17405083 ; 22391506 ; 24278036 ; 24895273 ; 25622056 ; 26527427
ChEBI ID
ChEBI:28088
CAS Number
446-72-0
TTD Drug ID
D0L4FS
Formula
C15H10O5
Canonical SMILES
C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
InChI
1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
InChIKey
TZBJGXHYKVUXJN-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
3'-hydroxygenistein DM006770
5281801
Oxidation - 3'-hydroxylation 1 [7]
6'-hydroxy-O-desmethylangolensin DM006760
20601635
Unclear 1 [8]
Genistein-4'-glucuronide DM006766 N. A. Unclear 1 [7]
Genistein-4'-sulfate DM006769
53997099
Unclear 1 [7]
Genistein-7-glucuronide DM006763
124934066
Unclear 1 [7]
Genistein-7-sulfate DM006768
10291508
Unclear 1 [7]
4-ethylphenol DM006762
31242
Unclear 2 [8]
4-hydroxyphenyl-2-propionic acid DM006761
102526
Hydrolysis - Hydrolysis 2 [8]
Genistein 4'-Glucuronide-7-Sulfate DM006767
102339163
Unclear 2 [7]
Genistein 7-Glucuronide-4'-Sulfate DM006764
156960888
Unclear 2 [7]
Genistein-4',7-diglucuronide DM006765
101519310
Unclear 2 [7]
4-ethylphenol DM006762
31242
Unclear 3 [8]
⏷ Show the Full List of 12  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007304 BIO-300 6'-hydroxy-O-desmethylangolensin Unclear Unclear [8]
MR007308 BIO-300 Genistein-7-glucuronide Unclear UGT [7]
MR007311 BIO-300 Genistein-4'-glucuronide Unclear UGT [7]
MR007314 BIO-300 Genistein-7-sulfate Unclear SULT [7]
MR007316 BIO-300 Genistein-4'-sulfate Unclear SULT [7]
MR007318 BIO-300 3'-hydroxygenistein Oxidation - 3'-hydroxylation CYP [7]
MR007305 6'-hydroxy-O-desmethylangolensin 4-hydroxyphenyl-2-propionic acid Hydrolysis - Hydrolysis Unclear [8]
MR007307 6'-hydroxy-O-desmethylangolensin 4-ethylphenol Unclear Unclear [8]
MR007312 Genistein-4'-glucuronide Genistein 4'-Glucuronide-7-Sulfate Unclear SULT [7]
MR007313 Genistein-4'-glucuronide Genistein-4',7-diglucuronide Unclear UGT [7]
MR007317 Genistein-4'-sulfate Genistein 7-Glucuronide-4'-Sulfate Unclear UGT [7]
MR007309 Genistein-7-glucuronide Genistein 7-Glucuronide-4'-Sulfate Unclear SULT [7]
MR007310 Genistein-7-glucuronide Genistein-4',7-diglucuronide Unclear UGT [7]
MR007315 Genistein-7-sulfate Genistein 4'-Glucuronide-7-Sulfate Unclear UGT [7]
MR007306 4-hydroxyphenyl-2-propionic acid 4-ethylphenol Unclear Unclear [8]
⏷ Show the Full List of 15 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[3]
Unclear metabolic mechanism (DME-unclear) DME1289 Tannerella forsythia Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1463 Slackia isoflavoniconvertens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME2045 Eubacterium ramulus Not Available Not Available [6]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Sulfotransferase 2A1 (SULT2A1) DME0074 Km = 0.041 microM
ST2A1_HUMAN
[3]
References
1 New drugs in development for the treatment of endometriosis. Expert Opin Investig Drugs. 2008 Aug;17(8):1187-202.
2 Differential mechanisms for the inhibition of human cytochrome P450 1A2 by apigenin and genistein. J Biochem Mol Toxicol. 2010 Jul-Aug;24(4):230-4.
3 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
4 Bacteroides uniformis is a putative bacterial species associated with the degradation of the isoflavone genistein in human feces. J Nutr. 2011 Jun;141(6):1120-6.
5 Daidzein and genistein are converted to equol and 5-hydroxy-equol by human intestinal Slackia isoflavoniconvertens in gnotobiotic rats. J Nutr. 2012 Jan;142(1):40-6.
6 Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiol Lett. 2002 Mar 5;208(2):197-202.
7 Genistein: Dual Role in Women's Health
8 Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism

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