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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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Targets

Primary TargetPharmacologyConditionPotency
2.4 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of HIV activation in latently infected cells by flavonoid compounds.
1996 Jan 1
Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.
1998 Feb
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
1998 Oct
Expression of antioxidant proteins in human intestinal Caco-2 cells treated with dietary flavonoids.
1999 Nov 15
Cytotoxic activity of low molecular weight polyphenols against human oral tumor cell lines.
2000 Jul-Aug
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Effect of xenoestrogen exposure on the expression of cytochrome P450 isoforms in rainbow trout liver.
2002 Nov
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
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
Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.
2003 Mar
Flavone and isoflavone phytoestrogens are agonists of estrogen-related receptors.
2003 Nov
Natural products for dental caries prevention.
2004 Fall
Recombinant human estrogen, androgen and progesterone receptors for detection of potential endocrine disruptors.
2004 Feb
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.
2004 Jan 9
Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover).
2004 Oct 20
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
Dose-response effects of phytoestrogens on the activity and expression of 3beta-hydroxysteroid dehydrogenase and aromatase in human granulosa-luteal cells.
2005 Aug
Metabolic engineering of isoflavonoid biosynthesis in alfalfa.
2005 Aug
Comparison of the in vitro estrogenic activities of compounds from hops (Humulus lupulus) and red clover (Trifolium pratense).
2005 Aug 10
Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.
2005 Dec
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
The phytoestrogen biochaninA weakens acute cardiac allograft rejection without affecting the reproductive system.
2005 Oct
Differential modulation of ochratoxin A absorption across Caco-2 cells by dietary polyphenols, used at realistic intestinal concentrations.
2005 Oct 15
Estrogen-related receptors as emerging targets in cancer and metabolic disorders.
2006
Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.
2006 Jul
The chemical and biologic profile of a red clover (Trifolium pratense L.) phase II clinical extract.
2006 Mar
Responsiveness to estradiol-17beta and to phytoestrogens in primary human osteoblasts is modulated differentially by high glucose concentration.
2006 May
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
The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity.
2006 May-Jun
Phytoestrogens and their low dose combinations inhibit mRNA expression and activity of aromatase in human granulosa-luteal cells.
2006 Nov
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones.
2006 Sep
Flavonoids modulate monocarboxylate transporter-1-mediated transport of gamma-hydroxybutyrate in vitro and in vivo.
2007 Feb
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
Establishment of a transgenic yeast screening system for estrogenicity and identification of the anti-estrogenic activity of malachite green.
2008 Dec 15
NMR spectral assignments of a new [C--O--C] isoflavone dimer from Andira surinamensis.
2008 Jan
Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.
2008 Jan-Feb
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.
2009 Mar 16
Novel screening method for potential skin-whitening compounds by a luciferase reporter assay.
2010
Syntheses, characterization and antitumor activities of transition metal complexes with isoflavone.
2010 Apr
Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications.
2010 Feb 15
Biochanin A induction of sulfotransferases in rats.
2010 Mar-Apr
The characterisation of structural and antioxidant properties of isoflavone metal chelates.
2010 Oct
Isoflavones enhance interleukin-17 gene expression via retinoic acid receptor-related orphan receptors α and γ.
2015 Mar 2
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
Created
by admin
on Fri Dec 15 17:46:44 GMT 2023
Edited
by admin
on Fri Dec 15 17:46:44 GMT 2023
Record UNII
U13J6U390T
Record Status Validated (UNII)
Record Version
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Name Type Language
BIOCHANIN A
MI   USP-RS  
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
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
DSLD 249 (Number of products:1)
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
Code System Code Type Description
FDA UNII
U13J6U390T
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
PUBCHEM
5280373
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
DRUG BANK
DB15334
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
MESH
C004541
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
NSC
123538
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-744-7
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
CHEBI
58194
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
NCI_THESAURUS
C28201
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
WIKIPEDIA
BIOCHANIN A
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
CAS
491-80-5
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
CHEBI
17574
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
RS_ITEM_NUM
1071381
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID1022394
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY
MERCK INDEX
m2501
Created by admin on Fri Dec 15 17:46:44 GMT 2023 , Edited by admin on Fri Dec 15 17:46:44 GMT 2023
PRIMARY Merck Index
Related Record Type Details
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