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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-01-23 13:20:48 UTC
Update Date2020-11-09 23:17:49 UTC
HMDB IDHMDB0005808
Secondary Accession Numbers
  • HMDB05808
Metabolite Identification
Common NameFormononetin
DescriptionFormononetin, also known as biochanin b, 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, formononetin is considered to be a flavonoid lipid molecule. Ononin is the 7-O-β-D-glucopyranoside of formononetin. Along with other phytoestrogens, it predominantly occurs in leguminous plants and Fabaceae, particularly in beans, such as green beans, lima beans, soy and many others, as the free aglycone or in form of its glucoside ononin. Formononetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, formononetin is found, on average, in the highest concentration in a few different foods, such as soy beans, sunflowers, and soy sauces and in a lower concentration in soy milks, other soy products, and soy yogurts. formononetin has also been detected, but not quantified in, several different foods, such as prunus (cherry, plum), pears, kales, purple mangosteens, and grapefruits. This could make formononetin a potential biomarker for the consumption of these foods. It can also be found in Maackia amurensis cell cultures.Formononetin promotes angiogenesis.
Structure
Data?1582752366
Synonyms
ValueSource
4'-O-MethyldaidzeinChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4-benzopyroneChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-oneChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-oneChEBI
7-Hydroxy-4'-methoxyisoflavoneChEBI
Biochanin bChEBI
FormononetolChEBI
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci)HMDB
7-Hydroxy-4'-methoxy-isoflavoneHMDB
7-Hydroxy-4'-methoxy-isoflavone (8ci)HMDB
Formononetin, 4-(14)C-labeledHMDB
Chemical FormulaC16H12O4
Average Molecular Weight268.268
Monoisotopic Molecular Weight268.073558866
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 KeyHKQYGTCOTHHOMP-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent4'-O-methylisoflavones
Alternative Parents
Substituents
  • 4p-o-methylisoflavone
  • Hydroxyisoflavonoid
  • Isoflavone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity74.18 m³·mol⁻¹ChemAxon
Polarizability27.86 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34beSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-0490000000-e26e3143b0047535b40cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02or-3897000000-5e35eab52b4bd3010fa5Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-006t-0960000000-882facb1d6090879f469Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-006t-0960000000-882facb1d6090879f469Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-006t-0960000000-882facb1d6090879f469Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-006t-0960000000-882facb1d6090879f469Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0090000000-c85f2c5d083aef27307aSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-1c961341bd2d8a5a1789Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0uxr-0090000000-0755787b026efa8867b7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-9e7db78f88f3bcea3676Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fka-0590000000-9b048aa233ab295b38b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uxr-0290000000-14118223ff7a3a92da15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-641b16fcdf1e38d31ff3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-b0f1307bbe6403a8d785Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fl1-0970000000-c5c59bf872295bb5bd11Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-f27b95e98c653affcd28Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-5f9bf767f99890c80fc6Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0uxr-0090000000-27bc455d2b7dd9e8c49bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0uxr-0090000000-40ec683117d5ddae2909Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0uxr-0090000000-13fe7148a164de5bc698Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-006t-0960000000-882facb1d6090879f469Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0udi-0090000000-c85f2c5d083aef27307aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-014i-0090000000-1c961341bd2d8a5a1789Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0007 (0.0002-0.0011) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 395 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID395
FooDB IDFDB012219
KNApSAcK IDC00002525
Chemspider ID4444070
KEGG Compound IDC00858
BioCyc IDFORMONONETIN
BiGG IDNot Available
Wikipedia LinkFormononetin
METLIN IDNot Available
PubChem Compound5280378
PDB IDNot Available
ChEBI ID18088
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed:16108819 ]