Genistein

Synonyms :
4′,5, 7-Trihydroxyisoflavone, 5,7,4′-Trihydroxyisoflavone, Genisteol, Genisterin

Status : investigational

Category

Protein Kinase Inhibitors

Description

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. [Wikipedia] 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. [1] 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. [Wikipedia]

Used

Currently Genistein is being studied in clinical trials as a treatment for prostate cancer.

Mechanism Of Action

Genistein may inhibit cancer cell growth by blocking enzymes required for cell growth. Genistein may decrease cardiovascular risk in postmenopausal women by interacting with the nuclear estrogen receptors to alter the transcription of cell specific genes. In randomized clinical trials, genistein was seen to increase the ratio of nitric oxide to endothelin and improved flow-mediated endothelium dependent vasodilation in healthy postmenopausal women. [1] In addition, genistein may have beneficial effects on glucose metabolism by inhibiting islet tyrosine kinase activity as well as insulin release dependent on glucose and sulfonylurea. [1]

Chemical Classification

This compound belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Isoflavones

Organic compounds

Phenylpropanoids and polyketides

Isoflavonoids

Isoflav-2-enes

Chemical Name

4′,5, 7-Trihydroxyisoflavone

Calculated Property

kind Value Source
logP 3.04 ALOGPS
logS -3.3 ALOGPS
Water Solubility 1.23e-01 g/l ALOGPS
logP 3.08 ChemAxon
IUPAC Name 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one ChemAxon
Traditional IUPAC Name genistein ChemAxon
Molecular Weight 270.2369 ChemAxon
Monoisotopic Weight 270.05282343 ChemAxon
SMILES OC1=CC=C(C=C1)C1=COC2=C(C(O)=CC(O)=C2)C1=O ChemAxon
Molecular Formula C15H10O5 ChemAxon
InChI 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 ChemAxon
InChIKey InChIKey=TZBJGXHYKVUXJN-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 86.99 ChemAxon
Refractivity 71.68 ChemAxon
Polarizability 26.59 ChemAxon
Rotatable Bond Count 1 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 6.61 ChemAxon
pKa (strongest basic) -5.2 ChemAxon
Physiological Charge -1 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Estrogen receptor beta : in Human
  • DNA topoisomerase 2-alpha : in Human
  • Protein-tyrosine kinase 2-beta : in Human
  • Nuclear receptor coactivator 1 : in Human
  • Estrogen receptor : in Human
  • Nuclear receptor coactivator 2 : in Human