Biochanin A

Biochanin A
Names
	IUPAC name 5,7-Dihydroxy-3-(4-methoxyphenyl)chromen-4-one
	Other names Biochanin; 4'-Methylgenistein; olmelin; Biochanine A; Biochanin-A; Genistein 4-methyl ether; 5,7-Dihydroxy-4'-methoxyisoflavone
Identifiers
CAS Number	491-80-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17574 ;
ChEMBL	ChEMBL131921 ;
ChemSpider	4444068 ;
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829;
KEGG	C00814 ;
PubChem CID	5280373;
CompTox Dashboard (EPA)	DTXSID1022394 ;
	InChI InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 Key: WUADCCWRTIWANL-UHFFFAOYSA-N ; InChI=1/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 Key: WUADCCWRTIWANL-UHFFFAOYAM;
	SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O;
Properties
Chemical formula	C16H12O5
Molar mass	284.267 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover ^[1] in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes.

Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis.^{[medical citation needed]} It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.^[2]

Metabolism

The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP⁺ to produce biochanin A, NADPH, and H⁺. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside).

References

^ Medjakovic, S.; Jungbauer, A. (2008). "Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID 18060767.
^ Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology. 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565.

[1] Medjakovic, S.; Jungbauer, A. (2008). "Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID 18060767.

[2] Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology. 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565.

[1]

[2]

v t e Isoflavones and their glycosides
Isoflavones	Daidzein Genistein Orobol
O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin
Glycosides	Daidzin Genistin Iridin Mirificin Ononin Puerarin Sophoricoside Tectoridin
Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone
Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone
Derivatives	Anagyroidisoflavone A and B Irilone Pseudobaptigenin Rotenoids
Synthetic	Ipriflavone

v t e Receptor/signaling modulators
Amino acids and similar/related	Amino acids and related: GABA receptor modulators GABA_A receptor positive modulators GABA metabolism and transport modulators GHB receptor modulators Glutamate metabolism and transport modulators Glycine receptor modulators Ionotropic glutamate receptor modulators Metabotropic glutamate receptor modulators Monoamines: Adrenergic receptor modulators Dopamine receptor modulators Histamine receptor modulators Melatonin receptor modulators Monoamine metabolism modulators Monoamine neurotoxins Monoamine releasing agents Monoamine reuptake inhibitors Serotonin receptor modulators hTAAR modulators Acetylcholine: Acetylcholine metabolism and transport modulators Muscarinic acetylcholine receptor modulators Nicotinic acetylcholine receptor modulators Others: Imidazoline receptor modulators Purine receptor modulators Sigma receptor modulators Thyroid hormone receptor modulators
Lipids	Eicosanoids: Cannabinoid receptor modulators Leukotriene signaling modulators Prostanoid signaling modulators Phospholipids: Lysophospholipid signaling modulators PAF receptor modulators Steroids: Androgen receptor modulators Estrogen receptor modulators Glucocorticoid receptor modulators Mineralocorticoid receptor modulators Progesterone receptor modulators Steroid metabolism modulators Other nuclear receptors: Aryl hydrocarbon receptor modulators Estrogen-related receptor modulators FXR and LXR modulators PPAR modulators Retinoid receptor modulators Vitamin D receptor modulators Xenobiotic-sensing receptor modulators
Peptides/proteins	Peptides: Angiotensin receptor modulators GH/IGF-1 axis signaling modulators GnRH and gonadotropin receptor modulators Melanocortin receptor modulators Neurokinin receptor modulators Opioid receptor modulators Oxytocin and vasopressin receptor modulators Cytokines: Cytokine receptor modulators Chemokine receptor modulators Interleukin receptor modulators TNF receptor superfamily modulators Growth factors: Growth factor receptor modulators TGFβ receptor superfamily modulators
Others and non-receptor	Enzymes: Cytochrome P450 modulators Histone deacetylase inhibitors Phosphodiesterase inhibitors Ion channels: Ion channel modulators TRP channel modulators Transporters: Sodium-glucose transporter modulators Symporter inhibitors Others: Nitric oxide signaling modulators

Metabolism

See also

References