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=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

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 8297		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
Inhibition of HIV activation in latently infected cells by flavonoid compounds.	1996 Jan 1	8825617
Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.	1998 Feb	9435150
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.	1998 Oct	9751507
Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids.	1999 Nov 15	10656621
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.	2000 Jul-Aug	10953322
Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts.	2002 Aug 1	12111696
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.	2002 Jul	12224631
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.	2002 Nov	12389925
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
Identification of CYP1A2 as the main isoform for the phase I hydroxylated metabolism of genistein and a prodrug converting enzyme of methylated isoflavones.	2003 Jul	12814970
Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.	2003 Mar	12598185
Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.	2003 Nov	14638870
Natural products for dental caries prevention.	2004 Fall	15383236
Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.	2004 Feb	14579009
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).	2004 Oct 20	15479032
25-hydroxyvitamin D3-1alpha-hydroxylase is expressed in human vascular smooth muscle cells and is upregulated by parathyroid hormone and estrogenic compounds.	2005 Apr 5	15795327
Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.	2005 Aug	16023337
Metabolic engineering of isoflavonoid biosynthesis in alfalfa.	2005 Aug	16006598
Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).	2005 Aug 10	16076101
Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.	2005 Dec	16188329
Metabolic O-demethylation does not alter the influence of isoflavones on the biophysical properties of membranes and MRP1-like protein transport activity.	2005 Jan 15	15581599
The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.	2005 Oct	16223672
Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.	2005 Oct 15	15955639
Estrogen-related receptors as emerging targets in cancer and metabolic disorders.	2006	16515477
Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.	2006 Jul	16903077
The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract.	2006 Mar	16566672
Responsiveness to estradiol-17beta and to phytoestrogens in primary human osteoblasts is modulated differentially by high glucose concentration.	2006 May	16621514
Up-regulation of interleukin-4 production via NF-AT/AP-1 activation in T cells by biochanin A, a phytoestrogen and its metabolites.	2006 May 1	16169028
The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity.	2006 May-Jun	16735947
Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells.	2006 Nov	16965912
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones.	2006 Sep	16598420
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.	2007 Feb	17108059
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 Nov-Dec	17659868
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.	2008 Dec 15	18980245
NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.	2008 Jan	18098226
Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.	2008 Jan-Feb	18386479
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.	2009 Mar 16	19007764
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.	2010	21071833
Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone.	2010 Apr	20015553
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.	2010 Feb 15	19913605
Biochanin A induction of sulfotransferases in rats.	2010 Mar-Apr	20391625
The characterisation of structural and antioxidant properties of isoflavone metal chelates.	2010 Oct	20656356
Isoflavones enhance interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.	2015 Mar 2	25583575
In vivo prediction of CYP-mediated metabolic interaction potential of formononetin and biochanin A using in vitro human and rat CYP450 inhibition data.	2015 Nov 19	26278343

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

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

NSC-123538

Code

English

BIOCHANINE A

Common Name

English

BIOCHANIN A (CONSTITUENT OF RED CLOVER) [DSC]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C599