BIOCHANIN A

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 Search

SMILES

COC1=CC=C(C=C1)C2=COC3=C(C2=O)C(O)=CC(O)=C3

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

Description
Sources: https://doi.org/10.3892/or.2017.5953 | https://www.ncbi.nlm.nih.gov/pubmed/29305928

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 Target	Pharmacology	Condition	Potency
Fatty-acid amide hydrolase 1 2 Target ID: O00519 Gene ID: 2166.0 Gene Symbol: FAAH Target Organism: Homo sapiens (Human) Sources: DOI: 10.1111/j.1476-5381.2010.00716.x retrieved from http://onlinelibrary.wiley.com/doi/10.1111/j.1476-5381.2010.00716.x/abstract	Inhibitor 8504		2.4 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29305928	Primary		Basic research	Unknown Approved Use Unknown
Head and neck squamous cell carcinoma 32 Sources: https://doi.org/10.3892/or.2017.5953	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vivo prediction of CYP-mediated metabolic interaction potential of formononetin and biochanin A using in vitro human and rat CYP450 inhibition data.	2015-11-19	26278343
Isoflavones enhance interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.	2015-03-02	25583575
The characterisation of structural and antioxidant properties of isoflavone metal chelates.	2010-10	20656356
Biochanin A induction of sulfotransferases in rats.	2010-04-15	20391625
Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone.	2010-04	20015553
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.	2010-02-15	19913605
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.	2010	21071833
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.	2009-03-16	19007764
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.	2008-12-15	18980245
Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.	2008-04-05	18386479
NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.	2008-01	18098226
25 hydroxy-vitamin D(3)-1alpha hydroxylase expression and activity in cultured human osteoblasts and their modulation by parathyroid hormone, estrogenic compounds and dihydrotestosterone.	2007-02-01	17659868
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.	2007-02	17108059
Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells.	2006-11	16965912
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006-11	16497524
Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones.	2006-09	16598420
Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.	2006-07	16903077
The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity.	2006-06-01	16735947
Up-regulation of interleukin-4 production via NF-AT/AP-1 activation in T cells by biochanin A, a phytoestrogen and its metabolites.	2006-05-01	16169028
Responsiveness to estradiol-17beta and to phytoestrogens in primary human osteoblasts is modulated differentially by high glucose concentration.	2006-05	16621514
The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract.	2006-03	16566672
Estrogen-related receptors as emerging targets in cancer and metabolic disorders.	2006	16515477
Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.	2005-12	16188329
Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.	2005-10-15	15955639
The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.	2005-10	16223672
Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).	2005-08-10	16076101
Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.	2005-08	16023337
Metabolic engineering of isoflavonoid biosynthesis in alfalfa.	2005-08	16006598
25-hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds.	2005-04-05	15795327
Metabolic O-demethylation does not alter the influence of isoflavones on the biophysical properties of membranes and MRP1-like protein transport activity.	2005-01-15	15581599
Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).	2004-10-20	15479032
Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.	2004-02	14579009
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004-01-09	14557274
Natural products for dental caries prevention.	2004	15383236
Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.	2003-11	14638870
Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.	2003-07	12814970
Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.	2003-03	12598185
Effects of soy isoflavones on apoptosis induction and G2-M arrest in human hepatoma cells involvement of caspase-3 activation, Bcl-2 and Bcl-XL downregulation, and Cdc2 kinase activity.	2003	12791511
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.	2002-11	12389925
Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts.	2002-08-01	12111696
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002-07	12224631
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000-08-23	10953322
Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids.	1999-11-15	10656621
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.	1998-10	9751507
Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.	1998-02	9435150
Inhibition of HIV activation in latently infected cells by flavonoid compounds.	1996-01-01	8825617

Patents

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.

Name

Type

Language

BIOCHANIN A

Common Name

English

NSC-123538

Preferred Name

English

BIOCHANIN A [USP-RS]

Common Name

English

5,7-DIHYDROXY-4'-METHOXYISOFLAVONE

Common Name

English

BIOCHANIN A [MI]

Common Name

English

BIOCHANIN

Common Name

English

4'-METHYLGENISTEIN

Common Name

English

BIOCHANINE A

Common Name

English

BIOCHANIN A (CONSTITUENT OF RED CLOVER) [DSC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C599