Structure Database (LMSD)

Common Name
Biochanin A
Systematic Name
5,7-Dihydroxy-4'-methoxyisoflavone
Synonyms
  • Pratensol
LM ID
LMPK12050229
Formula
Exact Mass
Calculate m/z
284.068475
Status
Curated

Classification

Biological Context

Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity.1,2 Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects.3 Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 µM) and has also been shown to activate a PPARα promoter.4 Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis.5 Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 µM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 µM).6,7

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Viridiplantae (#33090)
Flavonoid imported from http://metabolomics.jp/
Trifolium pratense (#57577)
Magnoliopsida (#3398)
Chemical Studies on “Clover Sickness”,
Agric Biol Chem, 1969

String Representations

InChiKey (Click to copy)
WUADCCWRTIWANL-UHFFFAOYSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1(O)=CC2OC=C(C3C=CC(OC)=CC=3)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 21
Rings 3
Aromatic Rings 3
Rotatable Bonds 2
Van der Waals Molecular Volume 238.41
Topological Polar Surface Area 79.90
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 5
logP 3.78
Molar Refractivity 77.91

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Updated at
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