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

General Information of Drug (ID: DR1986)
Drug Name
Daidzein
Synonyms
Daidzeol; K 251b; d-(+)-alpha-methylbenzylamine; daidzein; 4',7-Dihydroxy-iso-flavone; 4',7-Dihydroxyisoflavone; 4,7-Dihydroxyisoflavone; 486-66-8; 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-; 7,4'-Dihydroxyisoflavone; 7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone; 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one; BRN 0231523; CCRIS 7600; CHEMBL8145; EINECS 207-635-4; MFCD00016954; UNII-6287WC5J2L
Indication Dyslipidaemia [ICD11: 5C81] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 254.24 Topological Polar Surface Area 66.8
Heavy Atom Count 19 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
5281708
PubChem SID
12394 ; 623493 ; 5142892 ; 8144381 ; 8149155 ; 8616734 ; 11111095 ; 11114077 ; 11336198 ; 11361437 ; 11363149 ; 11365711 ; 11368273 ; 11371341 ; 11375568 ; 11376435 ; 11462409 ; 11483941 ; 11487869 ; 11490007 ; 11493778 ; 11494069 ; 11537432 ; 14720388 ; 14847806 ; 17389519 ; 17404975 ; 22391461 ; 24278030 ; 25622055 ; 26527426 ; 26613045 ; 26679806 ; 26747166 ; 26747167 ; 26752188 ; 26752189 ; 26758540 ; 29204010 ; 39315324 ; 46487931 ; 46500432 ; 47213225 ; 47216588 ; 47290947 ; 47440044 ; 47440045 ; 47440046 ; 47515129 ; 47959544
CAS Number
486-66-8
TTD Drug ID
D0SY2M
Formula
C15H10O4
Canonical SMILES
C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O
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
InChIKey
ZQSIJRDFPHDXIC-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',4',7-trihydroxyisoflavone DM006558
5284648
Oxidation - Hydrolyzationn 1 [3]
Dihydrodaidzein DM003821
176907
Reduction - Reduction 1 [4]
Unclear DM009999 N. A. Conjugation - Sulfation 1 [5]
O-desmethylangolensin DM006557
89472
Unclear 2 [4]
Tetrahydrodaidzein DM003818
129651510
Unclear 2 [4]
Equol DM003820
91469
Unclear 3 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007067 Daidzein Dihydrodazein Reduction - Reduction DZNR [4]
MR007071 Daidzein 3',4',7-trihydroxyisoflavone Oxidation - Hydrolyzationn cyp105d7 ... [3]
MR007072 Daidzein Unclear Conjugation - Sulfation SULT1A1 ... [5]
MR007068 Dihydrodazein Tetrahydrodaidzein Unclear DHDR [4]
MR007070 Dihydrodazein O-desmethylangolensin Unclear Unclear [4]
MR007069 Tetrahydrodaidzein Equol Unclear THDR [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102D1 (cyp102) DME1465 Streptomyces avermitilis
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 102D1 (cyp102D1) DMEN349 Streptomyces avermitilis Not Available Not Available [3]
daidzein reductase (DZNR) DMEN345 . Not Available Not Available [4]
dihydrodaidzein reductase (DHDR) DMEN346 . Not Available Not Available [4]
Pentalenic acid synthase (cyp105d7) DMEN348 Streptomyces avermitilis
CYP28_STRAW
1.14.15.11
[3]
Sulfotransferase 1A1 (SULT1A1) DME0008 Homo sapiens
ST1A1_HUMAN
2.8.2.1
[5]
Sulfotransferase 1E1 (SULT1E1) DME0061 Homo sapiens
ST1E1_HUMAN
2.8.2.4
[5]
Sulfotransferase 2A1 (SULT2A1) DME0074 Homo sapiens
ST2A1_HUMAN
2.8.2.14
[5]
tetrahydrodaidzein reductase (THDR) DMEN347 . Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1262 Enterorhabdus mucosicola Not Available Not Available [7]
Unclear metabolic mechanism (DME-unclear) DME1289 Tannerella forsythia Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1463 Slackia isoflavoniconvertens Not Available Not Available [8]
Unclear metabolic mechanism (DME-unclear) DME2045 Eubacterium ramulus Not Available Not Available [9]
⏷ Show the Full List of 14  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cytochrome P450 102D1 (cyp102) DME1465 Kcat/Km = 0.28 s-1microM-1
CPXB_BACMB
[2] , [3]
Sulfotransferase 2A1 (SULT2A1) DME0074 Km = 0.1673 microM
ST2A1_HUMAN
[5]
References
1 ClinicalTrials.gov (NCT01497977) Phytoestrogen Supplementation in Postmenopausal Women.
2 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
3 Engineering of daidzein 3'-hydroxylase P450 enzyme into catalytically self-sufficient cytochrome P450. Microb Cell Fact. 2012 Jun 14;11:81.
4 Metabolism of Daidzein and Genistein by Gut Bacteria of the Class Coriobacteriia
5 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
6 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.
7 Conversion of daidzein and genistein by an anaerobic bacterium newly isolated from the mouse intestine. Appl Environ Microbiol. 2008 Aug;74(15):4847-52.
8 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.
9 Anaerobic C-ring cleavage of genistein and daidzein by Eubacterium ramulus. FEMS Microbiol Lett. 2002 Mar 5;208(2):197-202.

If you find any error in data or bug in web service, please kindly report it to Dr. Yin and Dr. Li.