CHEBI:17574 - biochanin A

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ChEBI Name biochanin A
ChEBI ID CHEBI:17574
Definition A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:13903, CHEBI:3105, CHEBI:22876
Supplier Information ChemicalBook:CB8474490, eMolecules:481798, Selleckchem:Biochanin-A(4-Methylgenistein), ZINC000018847037
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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 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. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.
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Formula C16H12O5
Net Charge 0
Average Mass 284.26348
Monoisotopic Mass 284.06847
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
InChIKey WUADCCWRTIWANL-UHFFFAOYSA-N
SMILES COc1ccc(cc1)-c1coc2cc(O)cc(O)c2c1=O
Roles Classification
Biological Role(s): tyrosine kinase inhibitor
Any protein kinase inhibitor that interferes with the action of tyrosine kinase.
phytoestrogen
Any compound produced by a plant that happens to have estrogenic activity.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the action of fatty acid amide hydrolase (EC 3.5.1.99).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing biochanin A (CHEBI:17574) has role antineoplastic agent (CHEBI:35610)
biochanin A (CHEBI:17574) has role EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor (CHEBI:64033)
biochanin A (CHEBI:17574) has role phytoestrogen (CHEBI:76989)
biochanin A (CHEBI:17574) has role plant metabolite (CHEBI:76924)
biochanin A (CHEBI:17574) has role tyrosine kinase inhibitor (CHEBI:38637)
biochanin A (CHEBI:17574) is a 4'-methoxyisoflavones (CHEBI:133959)
biochanin A (CHEBI:17574) is a 7-hydroxyisoflavones (CHEBI:55465)
biochanin A (CHEBI:17574) is conjugate acid of biochanin A(1−) (CHEBI:58194)
Incoming 2,3-dihydrobiochanin A (CHEBI:15712) has functional parent biochanin A (CHEBI:17574)
biochanin A 7-O-β-D-glucoside (CHEBI:28751) has functional parent biochanin A (CHEBI:17574)
biochanin A 7-O-(6-O-malonyl-β-D-glucoside) (CHEBI:28556) has functional parent biochanin A (CHEBI:17574)
biochanin A(1−) (CHEBI:58194) is conjugate base of biochanin A (CHEBI:17574)
IUPAC Name
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Synonyms Sources
4'-methylgenistein ChemIDplus
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one ChemIDplus
5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one ChemIDplus
5,7-dihydroxy-4'-methoxyisoflavone ChemIDplus
Biochanin A KEGG COMPOUND
olmelin ChEBI
pratensol LIPID MAPS
Manual Xrefs Databases
BIOCHANIN-A MetaCyc
Biochanin_A Wikipedia
C00002510 KNApSAcK
C00814 KEGG COMPOUND
HMDB0002338 HMDB
LMPK12050229 LIPID MAPS
QSO PDBeChem
View more database links
Registry Numbers Types Sources
278107 Reaxys Registry Number Reaxys
491-80-5 CAS Registry Number ChemIDplus
Citations
McCormack PL, Keam SJ (2012)
Spotlight on dasatinib in chronic myeloid leukemia and Philadelphia chromosome-positive acute lymphoblastic leukemia.
BioDrugs : clinical immunotherapeutics, biopharmaceuticals and gene therapy 26, 61-64 [PubMed:22233429]
[show Abstract]
Last Modified
01 March 2018