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Record Information
Version1.0
Created at2023-06-09 20:02:35 UTC
Updated at2024-05-13 01:10:29 UTC
NP-MRD IDNP0331684
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,7-Dihydroxy-4-Methylisoflavone
DescriptionBiochanin 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. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside). The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. Biochanin A is an O-methylated isoflavone. Biochanin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Biochanin A is found, on average, in the highest concentration within a few different foods, such as milk (cow), peanuts, and soy beans and in a lower concentration in beers. Biochanin A has also been detected, but not quantified in, several different foods, such as lingonberries, savoy cabbages, garlics, garden rhubarbs, and red rices. This could make biochanin a a potential biomarker for the consumption of these foods. Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A is a potentially toxic compound. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro. It was first documented in 2006 (PMID: 16903077). Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes (PMID: 18565930) (PMID: 19679050) (PMID: 16651441) (PMID: 16598420).
Structure
Thumb
Synonyms
ValueSource
4'-MethylgenisteinChEBI
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-oneChEBI
5,7-Dihydroxy-4'-methoxyisoflavoneChEBI
OlmelinChEBI
PratensolChEBI
5,7-Dihydroxy-4'-methoxy-isoflavoneHMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)HMDB
BiochaninHMDB
Biochanine aHMDB
Genistein 4-methyl etherHMDB
Biochanin a, 14C-labeledHMDB
Chemical FormulaC16H12O5
Average Mass284.2670 Da
Monoisotopic Mass284.06847 Da
IUPAC Name5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Namebiochanin
CAS Registry NumberNot Available
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 KeyWUADCCWRTIWANL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2024-05-11View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600.133705802, CD3OD, simulated)ztmnb@umsystem.eduSumner lab, University of MissouriZach Tretter2024-05-11View Spectrum
Species
Species of OriginNot Available
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent4'-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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.44ALOGPS
logP3.22ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity76.17 m³·mol⁻¹ChemAxon
Polarizability28.68 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002338
DrugBank IDNot Available
Phenol Explorer Compound ID397
FoodDB IDFDB012223
KNApSAcK IDC00002510
Chemspider ID4444068
KEGG Compound IDC00814
BioCyc IDBIOCHANIN-A
BiGG IDNot Available
Wikipedia LinkBiochanin_A
METLIN IDNot Available
PubChem Compound5280373
PDB IDNot Available
ChEBI ID17574
Good Scents IDNot Available
References
General References
  1. 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 ]
  2. 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 ]
  3. Han EH, Kim JY, Jeong HG: Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Arch Pharm Res. 2006 Jul;29(7):570-6. doi: 10.1007/BF02969267. [PubMed:16903077 ]
  4. Vanden Berghe W, Dijsselbloem N, Vermeulen L, Ndlovu MN, Boone E, Haegeman G: Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity. Cancer Res. 2006 May 1;66(9):4852-62. doi: 10.1158/0008-5472.CAN-05-2957. [PubMed:16651441 ]
  5. Puli S, Lai JC, Bhushan A: Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones. J Neurooncol. 2006 Sep;79(2):135-42. doi: 10.1007/s11060-006-9126-0. Epub 2006 Apr 6. [PubMed:16598420 ]