Formononetin (CHEM016524)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:35:52 UTC
Update Date2016-11-09 01:15:25 UTC
Accession NumberCHEM016524
Identification
Common NameFormononetin
ClassSmall Molecule
DescriptionA member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by a methoxy group at position 4'.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical 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 Mass268.268 g/mol
Monoisotopic Mass268.074 g/mol
CAS Registry Number485-72-3
IUPAC Name7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Nameformononetin
SMILESCOC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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 , Positivesplash10-0fvj-0590000000-7aa92270f764672f14e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-0fka-0590000000-9b048aa233ab295b38b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0ftb-3960000000-589c4d2db0e1616f048eSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4e62264d96d83f1006b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-594ebd436c98639ce817Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4960000000-5532b99421a0a70d5ff2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-620f35334e7fd7404576Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-263722926d00078660baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-4970000000-6aab7e0d78fd4ac98c77Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005808
FooDB IDFDB012219
Phenol Explorer ID395
KNApSAcK IDC00002525
BiGG IDNot Available
BioCyc IDFORMONONETIN
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFormononetin
Chemspider ID4444070
ChEBI ID18088
PubChem Compound ID5280378
Kegg Compound IDC00858
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16108819
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24023812
3. Whalley J L; Bond T J; Botting N P Synthesis of 13C labelled daidzein and formononetin. Bioorganic & medicinal chemistry letters (1998), 8(18), 2569-72.
4. 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.
5. 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.
6. 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.
7. Whalley J L; Bond T J; Botting N P Synthesis of 13C labelled daidzein and formononetin. Bioorganic & medicinal chemistry letters (1998), 8(18), 2569-72.
8. 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.