Details of the Drug

General Information of Drug (ID: DMRFTJX)

Drug Name
daidzein
Synonyms
Daidzein; 486-66-8; 4',7-Dihydroxyisoflavone; Daidzeol; 7,4'-Dihydroxyisoflavone; 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one; 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-; 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one; 7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone; UNII-6287WC5J2L; CCRIS 7600; K 251b; 4,7-Dihydroxyisoflavone; EINECS 207-635-4; BRN 0231523; CHEMBL8145; 4',7-Dihydroxy-iso-flavone; d-(+)-alpha-methylbenzylamine; ,7-Dihydroxyisoflavone; 7,4'-dihydroxyisoflavone; DIADZEIN
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 254.24
Logarithm of the Partition Coefficient (xlogp) 2.5
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C15H10O4
IUPAC Name
7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
Canonical SMILES
C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O
InChI
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
Cross-matching ID
PubChem CID
5281708
ChEBI ID
CHEBI:28197
CAS Number
486-66-8
UNII
6287WC5J2L
DrugBank ID
DB13182
TTD ID
D0SY2M
VARIDT ID
DR00845
INTEDE ID
DR1986
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aldose reductase (AKR1B1) TTFBNVI ALDR_HUMAN Inhibitor [2]
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Inhibitor [3]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [3]
Estrogen-related receptor-alpha (ESRRA) TTPNQAC ERR1_HUMAN Agonist [4]
Estrogen-related receptor-beta (ESRRB) TTKF0XS ERR2_HUMAN Agonist [4]
Estrogen-related receptor-gamma (ESRRG) TT9ZRHB ERR3_HUMAN Agonist [4]
Short transient receptor potential channel 5 (TRPC5) TT32NQ1 TRPC5_HUMAN Activator [5]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [6]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Sulfotransferase 2A1 (SULT2A1) DE0P6LK ST2A1_HUMAN Substrate [7]
Cytochrome P450 102D1 (cyp102) DEUWAV0 CPXB_BACMB Substrate [8], [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Alkaline phosphatase, germ cell type (ALPG) OTCIM29R PPBN_HUMAN Gene/Protein Processing [10]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [11]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [12]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Protein Interaction/Cellular Processes [13]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [11]
Beta-enolase (ENO3) OT3HYKYI ENOB_HUMAN Gene/Protein Processing [14]
Breast cancer type 1 susceptibility protein (BRCA1) OT5BN6VH BRCA1_HUMAN Gene/Protein Processing [15]
Carnitine O-palmitoyltransferase 1, liver isoform (CPT1A) OTI862QH CPT1A_HUMAN Gene/Protein Processing [16]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [11]
Catechol O-methyltransferase (COMT) OTPWKTQG COMT_HUMAN Gene/Protein Processing [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Breast cancer resistance protein (ABCG2) DTP BCRP 9.93E-01 -1.09E-01 -5.77E-01
Sulfotransferase 2A1 (SULT2A1) DME SULT2A1 9.76E-01 2.62E-02 1.37E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 The balance between concurrent activation of ERs and PPARs determines daidzein-induced osteogenesis and adipogenesis. J Bone Miner Res. 2004 May;19(5):853-61.
2 1-Benzopyran-4-one antioxidants as aldose reductase inhibitors. J Med Chem. 1999 Jun 3;42(11):1881-93.
3 Isolation and structure elucidation of an isoflavone and a sesterterpenoic acid from Henriettella fascicularis. J Nat Prod. 2002 Dec;65(12):1749-53.
4 Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors. Mol Cancer Res. 2003 Nov;1(13):981-91.
5 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 490).
6 Effect of breast cancer resistance protein (Bcrp/Abcg2) on the disposition of phytoestrogens. Mol Pharmacol. 2007 Oct;72(4):967-75.
7 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
8 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
9 Engineering of daidzein 3'-hydroxylase P450 enzyme into catalytically self-sufficient cytochrome P450. Microb Cell Fact. 2012 Jun 14;11:81.
10 Estrogenic and genotoxic potential of equol and two hydroxylated metabolites of Daidzein in cultured human Ishikawa cells. Toxicol Lett. 2005 Jul 28;158(1):72-86. doi: 10.1016/j.toxlet.2005.02.011. Epub 2005 Apr 11.
11 Effects of soy isoflavones on apoptosis induction and G2-M arrest in human hepatoma cells involvement of caspase-3 activation, Bcl-2 and Bcl-XL downregulation, and Cdc2 kinase activity. Nutr Cancer. 2003;45(1):113-23. doi: 10.1207/S15327914NC4501_13.
12 Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):216-25. doi: 10.1016/j.jsbmb.2006.06.021. Epub 2006 Sep 11.
13 Xeno-oestrogens and phyto-oestrogens are alternative ligands for the androgen receptor. Asian J Androl. 2010 Jul;12(4):535-47. doi: 10.1038/aja.2010.14. Epub 2010 May 3.
14 Expression profiling of the estrogen responsive genes in response to phytoestrogens using a customized DNA microarray. FEBS Lett. 2005 Mar 14;579(7):1732-40.
15 Phytoestrogens activate estrogen receptor beta1 and estrogenic responses in human breast and bone cancer cell lines. Mol Nutr Food Res. 2007 Feb;51(2):171-7. doi: 10.1002/mnfr.200600091.
16 Positive regulation of hepatic carnitine palmitoyl transferase 1A (CPT1A) activities by soy isoflavones and L-carnitine. Eur J Nutr. 2006 Mar;45(3):159-64. doi: 10.1007/s00394-005-0576-5. Epub 2005 Dec 20.
17 Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells. Carcinogenesis. 2008 Feb;29(2):363-70.