Biochanin

Biochanin
Compound Structure:
Synonyms: biochanin A;491-80-5;Biochanin;4'-Methylgenistein;5,7-Dihydroxy-4'-methoxyisoflavone;5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one;olmelin;Pratensol;Biochanine A;Genistein 4-methyl ether;5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one;4-Methylgenistei
Compound ID: NMPC-678
PubChem ID:

5280373

Molecular Formula: C16H12O5
Canonical SMILES: COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
InChIKey: WUADCCWRTIWANL-UHFFFAOYSA-N
About the compound:

Biochanin A is a compound belonging to the class of 7-hydroxyisoflavones, characterized by its structure as a 7-hydroxyisoflavone that is further modified with a hydroxy group at position 5 and a methoxy group at position 4'. Recognized as a phytoestrogen, Biochanin A is noted for its potential benefits in dietary cancer prophylaxis. It functions in various capacities including as a phytoestrogen, a plant metabolite, an inhibitor of fatty acid amide hydrolase (EC 3.5.1.99), a tyrosine kinase inhibitor, and an antineoplastic agent. It belongs to both the groups of 7-hydroxyisoflavones and 4'-methoxyisoflavones, and chemically, it is a conjugate acid of a biochanin A(1-). Biochanin A is currently being studied in clinical trials, such as NCT02174666, which focuses on the treatment of postmenopausal osteopenia with isoflavones. As an O-methylated isoflavone, it is a natural organic compound categorized under the broad class of phytochemicals known as flavonoids. It can be found in various dietary sources, including red clover, soy, alfalfa sprouts, peanuts, chickpeas (Cicer arietinum), and other legumes. Apart from its role as a phytoestrogen with potential implications in cancer prevention, Biochanin A has also been identified as a weak inhibitor of fatty acid amide hydrolase in vitro. Furthermore, it has the capacity to block vasoconstriction in a dose-dependent manner, primarily through the inhibition of L-type calcium channels. This vasodilatory effect, notable at micromolar concentrations, may have clinical significance for the management of cardiovascular diseases. However, further research and clinical trials are needed to fully understand its efficacy and potential applications in medical treatments.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Property Name

Property Value

Molecular Weight

284.26 g/mol

XLogP3-AA

3

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

5

Rotatable Bond Count

2

Exact Mass

284.06847348 g/mol

Monoisotopic Mass

284.06847348 g/mol

Topological Polar Surface Area

76Ų

Heavy Atom Count

21

Formal Charge

0

Complexity

424

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Physical Description

Solid

Source: PubChem

Source Species: Talinum triangulare
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