Structure Database (LMSD)
Common Name
Genistein
Systematic Name
Synonyms
- Prunetol
3D model of Genistein
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Genistein is an isoflavonoid phytoestrogen that has been found in soybeans (G. max/S. hispida) and has kinase inhibitory, anticancer, pro-cancer, hepatoprotective, and antiviral properties.1 It inhibits the tyrosine kinases EGFR, pp50v-Src, and pp110gag-fes (IC50s = 6, 7-8, and 6.5 µg/ml, respectively) and decreases EGF-induced serine, threonine, and tyrosine phosphorylation of EGFR in A431 cells when used at a concentration of 20 µg/ml.2 Genistein inhibits proliferation and induces apoptosis in a variety of cancer cells, including Bel 7402 hepatocellular carcinoma cells when used at a concentration of 10 µg/ml.1,3 It reduces tumor invasion and angiogenesis in a Bel 7402 mouse subrenal capsule xenograft model when administered at a dose of 50 mg/kg per day.3 However, when administered at the same dose on postnatal days 1-5, genistein increases the incidence of uterine adenocarcinoma in a mouse model of cancer induced by the estrogen receptor agonist diethylstilbestrol (DES).4 It reduces lipid accumulation and inflammation in the liver of ovariectomized (OVX) and non-OVX female rats in a model of high-fat high-fructose diet-induced nonalcoholic hepatosteatosis (NASH) when administered at a dose of 16 mg/kg per day.5 Genistein (10 µM) also inhibits HIV-1 DNA synthesis in resting CD4+ T cells.6
This information has been provided by Cayman Chemical
References
2. Newbold, R.R., Banks, E.P., Bullock, B., et al. Uterine adenocarcinoma in mice treated neonatally with genistein. Cancer Res. 61(11), 4325-4328 (2001).
1. Akiyama, T., Ishida, J., Nakagawa, S., et al. Genistein, a specific inhibitor of tyrosine-specific protein kinases. The Journal of Biological Chemisty 262(1), 5592-5595 (1987).
5. Pummoung, S., Werawatganon, D., Klaikeaw, N., et al. Genistein-attenuated hepatic steatosis and inflammation in nonalcoholic steatohepatitis with bilateral ovariectomized rats. Pharmacogn. Mag. 14(55), 20-24 (2018).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Viridiplantae
(#33090)
Flavonoid imported from http://metabolomics.jp/
String Representations
InChiKey (Click to copy)
TZBJGXHYKVUXJN-UHFFFAOYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1(O)=CC2OC=C(C3=CC=C(O)C=C3)C(=O)C=2C(O)=C1
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
METABOLOMICS ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
20
Rings
3
Aromatic Rings
3
Rotatable Bonds
1
Van der Waals Molecular Volume
221.11
Topological Polar Surface Area
90.90
Hydrogen Bond Donors
3
Hydrogen Bond Acceptors
5
logP
3.48
Molar Refractivity
73.02
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