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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2369
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENISTEIN

SMILES

OC1=CC=C(C=C1)C2=COC3=C(C(O)=CC(O)=C3)C2=O

InChI

InChIKey=TZBJGXHYKVUXJN-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15909536 | https://www.ncbi.nlm.nih.gov/pubmed/28265354 | https://www.ncbi.nlm.nih.gov/pubmed/25996650 | https://clinicaltrials.gov/ct2/show/NCT01664650

GENISTEIN is an isoflavonoid derived from soy products. It inhibits protein-tyrosine kinase and topoisomerase-II (DNA topoisomerases, type II) activity and is used as an antineoplastic and antitumor agent. Experimentally, it has been shown to induce G2 phase arrest in human and murine cell lines. Additionally, genistein has antihelmintic activity. It has been determined to be the active ingredient in Felmingia vestita, which is a plant traditionally used against worms. It has also been demonstrated to be effective against intestinal parasites such as the common liver fluke, pork trematode and poultry cestode. Further, genistein is a phytoestrogen which has selective estrogen receptor modulator properties. It has been investigated in clinical trials as an alternative to classical hormone therapy to help prevent cardiovascular disease in postmenopausal women. Genistein can be found in food sources such as tofu, fava beans, soybeans, kudzu, and lupin. It is also present in certain cell cultures and medicinal plants.

CNS Activity

Originator

Approval Year

2007
205
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.11 µM [IC50]
Modulator
828
 6.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.
1999 Dec
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
Differential induction of tumor necrosis factor alpha and manganese superoxide dismutase by endotoxin in human monocytes: role of protein tyrosine kinase, mitogen-activated protein kinase, and nuclear factor kappaB.
2000 Mar
Activation of a uterine insulin-like growth factor I signaling pathway by clinical and environmental estrogens: requirement of estrogen receptor-alpha.
2000 Sep
Tyrosine kinase inhibitors against EGF receptor-positive malignancies.
2001
FAK induction in keratinocytes in an in vitro model of reepithelialization.
2001 Apr
Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase.
2001 Apr
PTH stimulates PLCbeta and PLCgamma isoenzymes in rat enterocytes: influence of ageing.
2001 Feb
Genistein potentiates the radiation effect on prostate carcinoma cells.
2001 Feb
Involvement of erythropoietin-induced cytosolic free calcium mobilization in activation of mitogen-activated protein kinase and DNA synthesis in vascular smooth muscle cells.
2001 Feb
Overexpression of BCL-X(L) underlies the molecular basis for resistance to staurosporine-induced apoptosis in PC-3 cells.
2001 Feb 15
Heparin-binding epidermal-growth-factor-like growth factor gene expression is induced by scrape-wounding epithelial cell monolayers: involvement of mitogen-activated protein kinase cascades.
2001 Feb 15
Vascular endothelial growth factor KDR receptor signaling potentiates tumor necrosis factor-induced tissue factor expression in endothelial cells.
2001 Feb 16
Molecular biology of transplant arteriosclerosis and sites of therapeutic intervention.
2001 Feb-Mar
Effects of tyrosine kinase inhibitors on cell death induced by sodium fluoride and pertussis toxin in the pancreatic beta-cell line, RINm5F.
2001 Jan
Interleukin-6 up-regulates the oxytocin receptor in cultured uterine smooth muscle cells.
2001 Mar
Ca(2+)-dependent production of reactive oxygen metabolites by human neutrophils in response to fluorinated propranolol analogues.
2001 Mar 1
Dihydropyridine calcium channel blockers inhibit ascorbic acid accumulation in human intestinal Caco-2 cells.
2001 Mar 2
Effects of simple aromatic compounds and flavonoids on Ca2+ fluxes in rat pituitary GH(4)C(1) cells.
2001 Mar 2
The "in vivo" and "ex vivo" roles of cylcooxygenase-2, nuclear factor-kappaB and protein kinases pathways in the up-regulation of B1 receptor-mediated contraction of the rabbit aorta.
2001 Mar 2
Patents

Patents

05679806
3
08742141
3
20010002407
14
JP2000053573A
5
JP2000302678A
4
JP2002510621A
8
JP2003081875A
4
JP2006298781A
5
JP2009519341A
24
JP2010168389A
2
JP2011528326A
17
JP2014201591A
2
JPH1087486A
4

Sample Use Guides

In Vivo Use Guide
54 mg/day in 2 tablets for 12 months.
Route of Administration: Oral
In Vitro Use Guide
Cells were cultured in Dulbecco’s modified Eagle’s medium (U2OS, HCT116) media containing fetal calf serum, penicillin, streptomycin, glutamine, nonessential amino acids (Hyclone). The long-term growth curves of both 10 μmol/L genistein-treated U2OS and HCT116 cells were then determined by MTS assay. The experiment was conducted for 60 days with measuring the population doublings (PD) every 2–4 days after each dilution.
Name Type Language
GENISTEIN
HSDB   INCI   MART.   MI   USP-RS   WHO-DD  
INCI   INN   USAN  
Official Name English
4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-
Systematic Name English
GENISTEIN [INCI]
Common Name English
BIO-300
Code English
GENISTEIN [HSDB]
Common Name English
SOPHORICOL
Common Name English
GENISTEIN [MART.]
Common Name English
genistein [INN]
Common Name English
GENISTEIN (CONSTITUENT OF RED CLOVER) [DSC]
Common Name English
4',5,7-TRIHYDROXYISOFLAVONE
Common Name English
NSC-36586
Code English
GENISTEIN [MI]
Common Name English
Genistein [WHO-DD]
Common Name English
5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
GENISTEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
GENISTEIN [USAN]
Common Name English
GENISTEIN [USP-RS]
Common Name English
FW-635I-2
Code English
5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-CHROMEN-4-ONE
Systematic Name English
SIPI-807-1
Code English
NPI-031L
Code English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
NCI_THESAURUS C1821
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
FDA ORPHAN DRUG 241107
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
NCI_THESAURUS C599
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
DSLD 1584 (Number of products:80)
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
Code System Code Type Description
RS_ITEM_NUM
1288816
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
CHEBI
28088
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
MERCK INDEX
m5696
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
GENISTEIN
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
DRUG BANK
DB01645
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
MESH
D019833
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
NSC
36586
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-174-9
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
DAILYMED
DH2M523P0H
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
FDA UNII
DH2M523P0H
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
NCI_THESAURUS
C1113
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
PUBCHEM
5280961
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
EVMPD
SUB13958MIG
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
SMS_ID
100000078160
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
INN
11073
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
CHEBI
27514
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
HSDB
7475
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
CAS
446-72-0
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022308
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
USAN
FG-12
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY
RXCUI
25696
Created by admin on Fri Dec 15 15:53:45 GMT 2023 , Edited by admin on Fri Dec 15 15:53:45 GMT 2023
PRIMARY RxNorm
CHEBI
74224
Created by admin on Fri Dec 15 15:53:44 GMT 2023 , Edited by admin on Fri Dec 15 15:53:44 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of GENISTEIN
SALT/SOLVATE (PARENT)
Structure of GENISTEIN SODIUM DIHYDRATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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