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Record Information
Version3.6
Creation Date2007-01-23 13:20:48 UTC
Update Date2016-02-11 01:07:17 UTC
HMDB IDHMDB05808
Secondary Accession NumbersNone
Metabolite Identification
Common NameFormononetin
DescriptionFormononetin are abundant in vegetables. It is a phyto-oestrogen that is a polyphenolic non-steroidal plant compound with oestrogen-like biological activity (PMID: 16108819 ). It can be the source of considerable estrogenic activity (http://www.herbalchem.net/Intermediate.htm).
Structure
Thumb
Synonyms
ValueSource
4'-O-MethyldaidzeinChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-oneChEBI
Biochanin bChEBI
FormononetolChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyroneHMDB
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci)HMDB
7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-oneHMDB
7-Hydroxy-4'-methoxy-isoflavoneHMDB
7-Hydroxy-4'-methoxy-isoflavone (8ci)HMDB
7-Hydroxy-4'-methoxyisoflavoneHMDB
Chemical FormulaC16H12O4
Average Molecular Weight268.2641
Monoisotopic Molecular Weight268.073558872
IUPAC Name7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nameformononetin
CAS Registry Number485-72-3
SMILES
COC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
InChI KeyInChIKey=HKQYGTCOTHHOMP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.04 mg/mLALOGPS
logP3.56ALOGPS
logP2.88ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)6.48ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.18 m3·mol-1ChemAxon
Polarizability27.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4e62264d96d83f1006b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-594ebd436c98639ce817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4960000000-5532b99421a0a70d5ff2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-620f35334e7fd7404576View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-263722926d00078660baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4970000000-6aab7e0d78fd4ac98c77View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.0007 (0.0002-0.0011) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID395
Phenol Explorer Metabolite ID395
FoodDB IDFDB012219
KNApSAcK IDC00002525
Chemspider ID4444070
KEGG Compound IDC00858
BioCyc ID2-HYDROXYFORMONONETIN
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05808
Metagene LinkHMDB05808
METLIN IDNot Available
PubChem Compound5280378
PDB IDNot Available
ChEBI ID18088
References
Synthesis ReferenceWhalley J L; Bond T J; Botting N P Synthesis of 13C labelled daidzein and formononetin. Bioorganic & medicinal chemistry letters (1998), 8(18), 2569-72.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Park J, Kim SH, Cho D, Kim TS: Formononetin, a phyto-oestrogen, and its metabolites up-regulate interleukin-4 production in activated T cells via increased AP-1 DNA binding activity. Immunology. 2005 Sep;116(1):71-81. [16108819 ]