Showing metabocard for Formononetin (BMDB0005808)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:48 UTC
Update Date2020-06-04 20:48:05 UTC
MCDB ID BMDB0005808
Secondary Accession Numbers
  • BMDB05808
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. Formononetin exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34be2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0016-2914000000-92598f879b703e3e34be2018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-0490000000-e26e3143b0047535b40c2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02or-3897000000-5e35eab52b4bd3010fa52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-006t-0960000000-882facb1d6090879f4692017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-006t-0960000000-882facb1d6090879f4692017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-006t-0960000000-882facb1d6090879f4692017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-006t-0960000000-882facb1d6090879f4692017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0090000000-c85f2c5d083aef27307a2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-014i-0090000000-1c961341bd2d8a5a17892017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0fk9-0390000000-60bac2bf99a8a69fbfa02017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0uxr-0090000000-0755787b026efa8867b72017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-014i-0090000000-9e7db78f88f3bcea36762017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0fvj-0590000000-7aa92270f764672f14e02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fka-0590000000-9b048aa233ab295b38b62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ftb-3960000000-589c4d2db0e1616f048e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uxr-0290000000-14118223ff7a3a92da152017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-641b16fcdf1e38d31ff32017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-b0f1307bbe6403a8d7852017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fl1-0970000000-c5c59bf872295bb5bd112017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4e62264d96d83f1006b42015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-594ebd436c98639ce8172015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4960000000-5532b99421a0a70d5ff22015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-620f35334e7fd74045762015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-263722926d00078660ba2015-05-27View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4970000000-6aab7e0d78fd4ac98c772015-05-27View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.0168 uM details
Detected and Quantified22 uM details
Detected and Quantified26 uM details
Detected and Quantified9.729 uM details
Detected and Quantified10 uM details
Detected and Quantified0.0399 - 0.0760 uM details
HMDB IDHMDB0005808
DrugBank IDNot Available
Phenol Explorer Compound ID395
FoodDB 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
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. Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. [PubMed:17576638 ]
  2. 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 ]
  3. 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 ]