AFCDB: Biochanin A (FDB012223)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:03 UTC

Update date

2019-11-26 03:06:25 UTC

Primary ID

FDB012223

Secondary Accession Numbers

FDB018509
FDB030699

Chemical Information

FooDB Name

Biochanin A

Description

Widespread isoflavone found in alfalfa (Medicago sativa), chick peas (Cicer arietinum) and white clover (Trifolium repens). Glycosides also widespread. Potential nutriceutical The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077); Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441); Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420); Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448).

CAS Number

491-80-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C16H12O5

IUPAC name

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

InChI Identifier

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

InChI Key

WUADCCWRTIWANL-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

Classification

Description

Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylisoflavones

Alternative Parents

Substituents

4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:17574 )
7-hydroxyisoflavones (CHEBI:17574 )
isoflavones (C00814 )
Isoflavonoids (C00814 )
Isoflavonoids (LMPK12050229 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Environmental role:

Environmental contaminant

Foods

Nuts and legumes:

Legumes:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 67.60%; H 4.25%; O 28.14%	DFC
Melting Point	Mp 215-216°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Biochanin A, 2 TMS, GC-MS Spectrum	splash10-03di-2944800000-78e1196ce4a6b5cc510e	Spectrum
GC-MS	Biochanin A, non-derivatized, GC-MS Spectrum	splash10-03di-2944800000-78e1196ce4a6b5cc510e	Spectrum
GC-MS	Biochanin A, non-derivatized, GC-MS Spectrum	splash10-03di-1833900000-f09d96dccb297f00dcd5	Spectrum
Predicted GC-MS	Biochanin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-0490000000-c605105233a09c99c287	Spectrum
Predicted GC-MS	Biochanin A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03k9-3439600000-64fa3b3cc333606e4699	Spectrum
Predicted GC-MS	Biochanin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014r-0190000000-7f6a864949fd18a14e8b	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-03yr-0790000000-5a2ccc494db05b9e19e7	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-1469c7dc6efca44dce49	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-014r-0190000000-7f6a864949fd18a14e8b	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 50V, Negative	splash10-03yr-0790000000-5a2ccc494db05b9e19e7	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-014i-0090000000-1469c7dc6efca44dce49	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0159-0090000000-48950d676f0cb98a7321	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0w9c-0490000000-9f316916713e817996ee	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0a4i-0019000000-09139525e32bfa06cffd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-014i-0190000000-3d2d9ae76aea2ba8e0d4	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-47e7f5888047896fbeab	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-0d44debd7dc24705b82a	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-4970000000-62cdcc296c60a0b9a572	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0090000000-47e7f5888047896fbeab	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0090000000-0d44debd7dc24705b82a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-4970000000-62cdcc296c60a0b9a572	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-57c90dbeeae680583b28	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-cfc655e2b327c5f14670	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue9-3890000000-4aefff84d287041c16e9	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-57c90dbeeae680583b28	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090000000-cfc655e2b327c5f14670	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ue9-3890000000-4aefff84d287041c16e9	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17574

Phenol-Explorer ID

397

DrugBank ID

Not Available

HMDB ID

HMDB02338

CRC / DFC (Dictionary of Food Compounds) ID

HFG01-K:HFG01-K

EAFUS ID

Not Available

Dr. Duke ID

BIOCHANIN-A|BIOCHANIN

BIGG ID

Not Available

KNApSAcK ID

C00002510

HET ID

QSO

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

397

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
17beta-hydroxysteroid-dehydrogenase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
5alpha-reductase inhibitor	50781	An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.	DUKE
alpha-reductase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
anti alcoholic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti carcinogenic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti cephalagic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti mutagenic			DUKE
anti proliferant			DUKE
anti prostat adenomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti prostatitic			DUKE

Showing 1 to 10 of 29 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

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References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Biochanin A (FDB012223)

Structure for FDB012223 (Biochanin A)