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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

Molecular Formula C15H10O5
Molecular Weight 270.2375
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
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
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
Effect of genistein-enriched diets on the endocrine process of gametogenesis and on reproduction efficiency of the rainbow trout Oncorhynchus mykiss.
2001 Feb
A common mechanism for cystic fibrosis transmembrane conductance regulator protein activation by genistein and benzimidazolone analogs.
2001 Feb
Assessment of CFTR chloride channel openers in intact normal and cystic fibrosis murine epithelia.
2001 Feb
Signaling events following chemokine receptor ligation in human dendritic cells at different developmental stages.
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
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.
2001 Feb 16
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
Modulation of noradrenaline-induced microvascular constriction by protein kinase inhibitors.
2001 Jan
Contractile actions of proteinase-activated receptor-derived polypeptides in guinea-pig gastric and lung parenchymal strips: evidence for distinct receptor systems.
2001 Jan
Leukotriene C(4) enhances the contraction of porcine tracheal smooth muscle through the activation of Y-27632, a rho kinase inhibitor, sensitive pathway.
2001 Jan
Growth hormone- and prolactin-induced proliferation of insulinoma cells, INS-1, depends on activation of STAT5 (signal transducer and activator of transcription 5).
2001 Jan
Activation of human neutrophils by technical toxaphene.
2001 Jan
Genistein inhibits nonoxidative ribose synthesis in MIA pancreatic adenocarcinoma cells: a new mechanism of controlling tumor growth.
2001 Jan
Agents that increase tyrosine phosphorylation activate a non-selective cation current in single rabbit portal vein smooth muscle cells.
2001 Jan 15
Salicylates inhibit T cell adhesion on endothelium under nonstatic conditions: induction of L-selectin shedding by a tyrosine kinase-dependent mechanism.
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
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Effect of intraovarian factors on porcine follicular cells: cumulus expansion, granulosa and cumulus cell progesterone production.
2001 Jan 31
Differential effects of protein tyrosine kinase inhibitors on interferon-gamma-induction of major histocompatibility complex class II and intercellular adhesion molecule-1 expression in human corneal epithelial cells.
2001 Jan-Feb
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
Effects of estrogens in vitro and in vivo on cartilage growth in the tilapia (Oreochromis mossambicus).
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
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
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

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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:43:51 UTC 2021
Edited
by admin
on Sat Jun 26 02:43:51 UTC 2021
Record UNII
DH2M523P0H
Record Status Validated (UNII)
Record Version
  • Download
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
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TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY