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Details

Stereochemistry ACHIRAL
Molecular Formula C16H12O5
Molecular Weight 284.2635
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIOCHANIN A

SMILES

COC1=CC=C(C=C1)C2=COC3=CC(O)=CC(O)=C3C2=O

InChI

InChIKey=WUADCCWRTIWANL-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H12O5
Molecular Weight 284.2635
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Biochanin A, a natural organic compound derived from herbal plants such as peanuts, soy, and red clover, possesses various pharmacological properties including antioxidant and anti-inflammatory. In addition, the compound has anticancer activity, which was shown in the following cells: head and neck squamous cell carcinoma and in osteosarcoma. In both cases, biochanin A induced apoptotic signaling pathway. It has also been found biochanin-A was an inhibitor of fatty acid amide hydrolase.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.4 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Biochanin A inhibited the hydrolysis of 0.5 µM anandamide by mouse, rat and human FAAH with IC50 values of 1.8, 1.4 and 2.4 µM respectively. The compound did not interact to any major extent with CB1 or CB2 receptors, nor with FAAH-2.
Substance Class Chemical
Record UNII
U13J6U390T
Record Status Validated (UNII)
Record Version