Structure Database (LMSD)

Common Name
Genistein
Systematic Name
Synonyms
  • Prunetol
LM ID
LMPK12050218
Formula
Exact Mass
Calculate m/z
270.052825
Status
Curated





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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