Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-01-23 13:20:48 UTC
Update Date2021-10-13 04:47:31 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. Formononetin is found, on average, in the highest concentration within a few different foods, such as milk (cow), soy beans (Glycine max), and sunflowers (Helianthus annuus) and in a lower concentration in miso, other soy product, and soy yogurt. Formononetin has also been detected, but not quantified in, several different foods, such as muscadine grapes (Vitis rotundifolia), wild celeries (Apium graveolens), strawberries (Fragaria X ananassa), ostrich ferns (Matteuccia struthiopteris), and red huckleberries (Vaccinium parvifolium). This could make formononetin a potential biomarker for the consumption of these foods. Formononetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Formononetin.
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
Formononetin, 4-(14)C-labeledMeSH
7-Hydroxy-3-(4-methoxyphenyl)-4H-benzopyran-4-one(9ci)HMDB
7-Hydroxy-4'-methoxy-isoflavoneHMDB
7-Hydroxy-4'-methoxy-isoflavone (8ci)HMDB
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 - 258 °CNot Available
Boiling Point479.40 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility157.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.960 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker169.03730932474
[M-H]-Not Available169.037http://allccs.zhulab.cn/database/detail?ID=AllCCS00001932
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP10(3.56) g/LALOGPS
logP10(2.88) g/LChemAxon
logS10(-3.8) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+163.47931661259
DarkChem[M-H]-164.46531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
FormononetinCOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O3696.4Standard polar33892256
FormononetinCOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O2647.8Standard non polar33892256
FormononetinCOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O2890.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Formononetin,1TMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C12999.2Semi standard non polar33892256
Formononetin,1TBDMS,isomer #1COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C13195.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Formononetin GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34be2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Formononetin GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34be2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formononetin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-0490000000-e26e3143b0047535b40c2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formononetin GC-MS (1 TMS) - 70eV, Positivesplash10-02or-3897000000-5e35eab52b4bd3010fa52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Formononetin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 50V, Negative-QTOFsplash10-006t-0960000000-882facb1d6090879f4692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 30V, Negative-QTOFsplash10-006t-0960000000-882facb1d6090879f4692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 10V, Negative-QTOFsplash10-006t-0960000000-882facb1d6090879f4692017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 40V, Negative-QTOFsplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 20V, Negative-QTOFsplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF , Negative-QTOFsplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 50V, Negative-QTOFsplash10-006t-0960000000-882facb1d6090879f4692017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 30V, Negative-QTOFsplash10-0udi-0090000000-c85f2c5d083aef27307a2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 10V, Negative-QTOFsplash10-014i-0090000000-1c961341bd2d8a5a17892017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 40V, Negative-QTOFsplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF 20V, Negative-QTOFsplash10-0uxr-0090000000-0755787b026efa8867b72017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin ESI-TOF , Negative-QTOFsplash10-014i-0090000000-9e7db78f88f3bcea36762017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin DI-ESI-qTof , Positive-QTOFsplash10-0fvj-0590000000-7aa92270f764672f14e02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin DI-ESI-qTof , Negative-QTOFsplash10-0fka-0590000000-9b048aa233ab295b38b62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin LC-ESI-qTof , Positive-QTOFsplash10-0ftb-3960000000-589c4d2db0e1616f048e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin LC-ESI-QTOF , negative-QTOFsplash10-0uxr-0290000000-14118223ff7a3a92da152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin LC-ESI-QTOF , negative-QTOFsplash10-014i-0090000000-641b16fcdf1e38d31ff32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin LC-ESI-QTOF , negative-QTOFsplash10-0udi-0090000000-b0f1307bbe6403a8d7852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Formononetin LC-ESI-QTOF , negative-QTOFsplash10-0fl1-0970000000-c5c59bf872295bb5bd112017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 10V, Positive-QTOFsplash10-014i-0090000000-4e62264d96d83f1006b42015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 20V, Positive-QTOFsplash10-014i-0090000000-594ebd436c98639ce8172015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 40V, Positive-QTOFsplash10-000i-4960000000-5532b99421a0a70d5ff22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 10V, Negative-QTOFsplash10-014i-0090000000-620f35334e7fd74045762015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 20V, Negative-QTOFsplash10-014i-0090000000-263722926d00078660ba2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 40V, Negative-QTOFsplash10-00kr-4970000000-6aab7e0d78fd4ac98c772015-05-27Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1504451
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 ]