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

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

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
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
Natural products for dental caries prevention.	2004 Fall	15383236
Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake.	2004 Jan 9	14557274
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
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
Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells.	2006 Jul	16903077
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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
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

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:46:44 UTC 2023` Edited by `admin` on `Fri Dec 15 17:46:44 UTC 2023`
Record UNII	U13J6U390T
Record Status	`Validated (UNII)`
Record Version

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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