Details of the Drug

General Information of Drug (ID: DM0JETC)

Drug Name
Genistein
Synonyms
Bonistein; GEN; Genestein; Genisteol; Genisterin; Prunetol; Sophoricol; Differenol A; G 6649; G10000; IN1327; NPI 031L; STO514; TNP00151; GENISTEIN (ENDOCRINE DISRUPTER); Lactoferrin-genistein; PTI G4660 (Genistein); PTI-G4660; SIPI 807-1; C.I. 75610; SIPI-9764-I; ENDOCRINE DISRUPTOR (GENISTEIN) (SEE ALSO GENISTEIN (446-72-0)); 4 inverted exclamation marka,5,7-Trihydroxyisoflavone; ,5,7-Trihydroxyisoflavone; 4',5, 7-Trihydroxyisoflavone; 4',5,7-Trihydroxy isoflavone; 4',5,7-Trihydroxyisoflavone; 4,5,7-Trihydroxyiso-flavone; 4,6,7-Trihydroxyisoflavone; 5,7,4'-Trihydroxyisoflavone; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone; 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
Indication
Disease Entry ICD 11 Status REF
Menopause symptom GA30.0 Phase 2/3 [1]
Prostate cancer 2C82.0 Phase 2 [2]
Affected Organisms
Humans and other mammalsHelminthic MicroorganismsParasitic nematodes and other roundworms
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 270.24
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H10O5
IUPAC Name
5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
Canonical SMILES
C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O
InChI
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
Cross-matching ID
PubChem CID
5280961
ChEBI ID
CHEMBL44
CAS Number
446-72-0
UNII
DH2M523P0H
DrugBank ID
DB01645
TTD ID
D0L4FS
VARIDT ID
DR00641
INTEDE ID
DR0768
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Modulator [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [5]
Sulfotransferase 2A1 (SULT2A1) DE0P6LK ST2A1_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
(3R)-3-hydroxyacyl-CoA dehydrogenase (HSD17B8) OTX1DWEF DHB8_HUMAN Gene/Protein Processing [7]
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [8]
1-acyl-sn-glycerol-3-phosphate acyltransferase beta (AGPAT2) OT5I4Y9K PLCB_HUMAN Gene/Protein Processing [9]
1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1 (PLCB1) OT9HYT7A PLCB1_HUMAN Gene/Protein Processing [10]
14-3-3 protein epsilon OT3WQXNA 1433E_HUMAN Gene/Protein Processing [11]
17-beta-hydroxysteroid dehydrogenase 14 (HSD17B14) OT0ETO72 DHB14_HUMAN Gene/Protein Processing [10]
17-beta-hydroxysteroid dehydrogenase type 1 (HSD17B1) OT6EBDHM DHB1_HUMAN Gene/Protein Processing [12]
182 kDa tankyrase-1-binding protein (TNKS1BP1) OTBIZECQ TB182_HUMAN Gene/Protein Processing [7]
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial (BCKDHA) OT0LHOZB ODBA_HUMAN Gene/Protein Processing [7]
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial (CYP27B1) OTTK98BH CP27B_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Menopause symptom
ICD Disease Classification GA30.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Estrogen receptor beta (ESR2) DTT ESR2 1.12E-20 -0.22 -0.7
Breast cancer resistance protein (ABCG2) DTP BCRP 1.46E-65 -1.41E+00 -1.41E+00
Cytochrome P450 1A2 (CYP1A2) DME CYP1A2 4.34E-02 -5.62E-03 -1.44E-02
Sulfotransferase 2A1 (SULT2A1) DME SULT2A1 8.40E-01 5.46E-03 3.67E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 ClinicalTrials.gov (NCT00355953) Vascular and Skeletal Protective Effects of Genistein in Postmenopausal Women. U.S. National Institutes of Health.
2 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. (Ligand id: 2826).
3 Company report (Axcentua)
4 Differential selectivity of efflux transporter inhibitors in Caco-2 and MDCK-MDR1 monolayers: a strategy to assess the interaction of a new chemical entity with P-gp, BCRP, and MRP2. J Pharm Sci. 2012 May;101(5):1888-97.
5 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.
6 Sulfation of environmental estrogens by cytosolic human sulfotransferases. Drug Metab Pharmacokinet. 2002;17(3):221-8.
7 Quantitative proteomics and transcriptomics addressing the estrogen receptor subtype-mediated effects in T47D breast cancer cells exposed to the phytoestrogen genistein. Mol Cell Proteomics. 2011 Jan;10(1):M110.002170.
8 Genistein potentiates the growth inhibitory effects of 1,25-dihydroxyvitamin D3 in DU145 human prostate cancer cells: role of the direct inhibition of CYP24 enzyme activity. Mol Cell Endocrinol. 2005 Sep 28;241(1-2):49-61.
9 Genistein and bisphenol A exposure cause estrogen receptor 1 to bind thousands of sites in a cell type-specific manner. Genome Res. 2012 Nov;22(11):2153-62.
10 Gene expression profiling in Ishikawa cells: a fingerprint for estrogen active compounds. Toxicol Appl Pharmacol. 2009 Apr 1;236(1):85-96.
11 A high concentration of genistein down-regulates activin A, Smad3 and other TGF-beta pathway genes in human uterine leiomyoma cells. Exp Mol Med. 2012 Apr 30;44(4):281-92.
12 Mammalian lignans and genistein decrease the activities of aromatase and 17beta-hydroxysteroid dehydrogenase in MCF-7 cells. J Steroid Biochem Mol Biol. 2005 Apr;94(5):461-7.
13 25-Hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds. Circulation. 2005 Apr 5;111(13):1666-71.