Bovine Metabolome Database: Showing metabocard for Biochanin A (BMDB0002338)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:54:16 UTC

Update Date

2020-06-04 20:47:06 UTC

BMDB ID

BMDB0002338

Secondary Accession Numbers

BMDB02338

Metabolite Identification

Common Name

Biochanin A

Description

Biochanin a, also known as olmelin or pratensol, 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. Thus, biochanin a is considered to be a flavonoid lipid molecule. Biochanin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Biochanin a is a potentially toxic compound.

Structure

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

Synonyms

Value	Source
4'-Methylgenistein	ChEBI
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one	ChEBI
5,7-Dihydroxy-4'-methoxyisoflavone	ChEBI
Olmelin	ChEBI
Pratensol	ChEBI
Biochanin a, 14C-labeled	MeSH
Genistein 4-methyl ether	MeSH
5,7-Dihydroxy-4'-methoxy-isoflavone	HMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)	HMDB
Biochanin	HMDB
Biochanine a	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

IUPAC Name

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

Traditional Name

biochanin

CAS Registry Number

491-80-5

SMILES

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

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

Chemical Taxonomy

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

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Biological Properties

Cellular Locations

Cell membrane
Membrane

Biospecimen Locations

Milk

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Milk	Detected and Quantified	5.558 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	7.493 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	1.161 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	1.442 uM	Not Specified	Not Specified	Normal	PMID: 18565930	details
Milk	Detected and Quantified	0.00457 +/- 0.000246 uM	Not Specified	Not Specified	Normal	PMID: 19679050	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002338

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Biochanin_A

METLIN ID

Not Available

PubChem Compound

5280373

PDB ID

Not Available

ChEBI ID

17574

References

Synthesis Reference

Gakhokidze, A. M. Synthesis of olmelin. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) (1950), 23 559-60.

Material Safety Data Sheet (MSDS)

Not Available

General References

Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. [PubMed:19679050 ]

Showing metabocard for Biochanin A (BMDB0002338)

Structure for BMDB0002338 (Biochanin A)