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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2375
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENISTEIN

SMILES

c1cc(ccc1-c2coc3cc(cc(c3c2=O)O)O)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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.11 µM [IC50]
6.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Tyrosine kinase inhibitors against EGF receptor-positive malignancies.
2001
FAK induction in keratinocytes in an in vitro model of reepithelialization.
2001 Apr
Mitogenic effect of oxidized low-density lipoprotein on vascular smooth muscle cells mediated by activation of Ras/Raf/MEK/MAPK pathway.
2001 Apr
Characterization of the serotonin receptor mediating contraction in the mouse thoracic aorta and signal pathway coupling.
2001 Apr
Differential effects of flavonoids on 3T3-L1 adipogenesis and lipolysis.
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 ErbB-2 in rheumatoid synovial cell growth.
2001 Feb
Effects of genistein on the periovulatory expression of messenger ribonucleic acid for matrix metalloproteinases and tissue inhibitors of metalloproteinases in the rat ovary.
2001 Feb
Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon.
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
Regulation of MAP kinase by calcium-sensing receptor in bovine parathyroid and CaR-transfected HEK293 cells.
2001 Feb
Effect of genistein-enriched diets on the endocrine process of gametogenesis and on reproduction efficiency of the rainbow trout Oncorhynchus mykiss.
2001 Feb
Detrimental effect of cancer preventive phytochemicals silymarin, genistein and epigallocatechin 3-gallate on epigenetic events in human prostate carcinoma DU145 cells.
2001 Feb 1
Cytokine regulation of the expression of estrogenic biosynthetic enzymes in cultured rat granulosa cells.
2001 Feb 14
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
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.
2001 Feb 16
Sex steroid receptor regulation by genistein in the prepubertal rat uterus.
2001 Feb 28
Molecular biology of transplant arteriosclerosis and sites of therapeutic intervention.
2001 Feb-Mar
The mechanism of maitotoxin-induced elevation of the cytosolic free calcium level in rat cerebrocortical synaptosomes.
2001 Jan
Genistein prevents the glucose autoxidation mediated atherogenic modification of low density lipoprotein.
2001 Jan
Comparative assessment of endocrine modulators with oestrogenic activity: I. Definition of a hygiene-based margin of safety (HBMOS) for xeno-oestrogens against the background of European developments.
2001 Jan
Secretory transport of p-aminohippuric acid across intestinal epithelial cells in Caco-2 cells and isolated intestinal tissue.
2001 Jan
[In vitro and in vivo study of regulation mechanisms of type I interleukin-1 receptor].
2001 Jan
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.
2001 Jan
Constitutive activation of Lck and Fyn tyrosine kinases in large granular lymphocytes infected with the gamma-herpesvirus agents of malignant catarrhal fever.
2001 Jan
Agents that increase tyrosine phosphorylation activate a non-selective cation current in single rabbit portal vein smooth muscle cells.
2001 Jan 15
The phytoestrogen genistein produces acute nitric oxide-dependent dilation of human forearm vasculature with similar potency to 17beta-estradiol.
2001 Jan 16
Leflunomide inhibits activation of inducible nitric oxide synthase in rat astrocytes.
2001 Jan 19
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors.
2001 Jan 23
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.
2001 Jan 31
Novel CFTR chloride channel activators identified by screening of combinatorial libraries based on flavone and benzoquinolizinium lead compounds.
2001 Jun 8
Interleukin-6 up-regulates the oxytocin receptor in cultured uterine smooth muscle cells.
2001 Mar
Differences in signal transduction pathways by which platelet-derived and fibroblast growth factors activate extracellular signal-regulated kinase in differentiating oligodendrocytes.
2001 Mar
Vascular endothelial growth factor and the in vivo increase in plasma extravasation in the hamster cheek pouch.
2001 Mar
Src tyrosine kinases and extracellular signal-regulated kinase 1/2 mitogen-activated protein kinases mediate pressure-induced c-fos expression in cannulated rat mesenteric small arteries.
2001 Mar
Bile acids induce eosinophil degranulation by two different mechanisms.
2001 Mar
Protein tyrosine kinase inhibitors alter human dopamine transporter activity in Xenopus oocytes.
2001 Mar
Phytoestrogens and gonadotropin-releasing hormone pulse generator activity and pituitary luteinizing hormone release in the rat.
2001 Mar
Adenosine-induced late preconditioning in mouse hearts: role of p38 MAP kinase and mitochondrial K(ATP) channels.
2001 Mar
Ca(2+)-dependent production of reactive oxygen metabolites by human neutrophils in response to fluorinated propranolol analogues.
2001 Mar 1
Initiation of polyoma virus origin-dependent DNA replication through STAT5 activation by human granulocyte-macrophage colony-stimulating factor.
2001 Mar 1
Paclitaxel sensitization of multidrug-resistant cells to chemotherapy is independent of the cell cycle.
2001 Mar 1
Corticosterone-induced rapid phosphorylation of p38 and JNK mitogen-activated protein kinases in PC12 cells.
2001 Mar 16
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
Effect of phytoestrogen and antioxidant supplementation on oxidative DNA damage assessed using the comet assay.
2001 Mar 7
Patents

Sample Use Guides

54 mg/day in 2 tablets for 12 months.
Route of Administration: Oral
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  
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
5,7-DIHYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
Systematic Name English
GENISTEIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
GENISTEIN [WHO-DD]
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 Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
NCI_THESAURUS C1821
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
FDA ORPHAN DRUG 241107
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
NCI_THESAURUS C599
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
DSLD 1584 (Number of products:80)
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
NCI_THESAURUS C1742
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
Code System Code Type Description
MERCK INDEX
M5696
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
GENISTEIN
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
DRUG BANK
DB01645
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
MESH
D019833
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-174-9
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
FDA UNII
DH2M523P0H
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
NCI_THESAURUS
C1113
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
PUBCHEM
5280961
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
EVMPD
SUB13958MIG
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
INN
11073
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
HSDB
7475
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
CAS
446-72-0
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
EPA CompTox
446-72-0
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY
USP_CATALOG
1288816
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY USP-RS
RXCUI
25696
Created by admin on Sat Jun 26 02:43:51 UTC 2021 , Edited by admin on Sat Jun 26 02:43:51 UTC 2021
PRIMARY RxNorm