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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2019-10-11 14:53:34 UTC
Update Date2022-03-07 03:18:18 UTC
HMDB IDHMDB0240517
Secondary Accession NumbersNone
Metabolite Identification
Common NameFormononetin 7-glucuronide
DescriptionFormononetin 7-glucuronide belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position. Based on a literature review very few articles have been published on Formononetin 7-glucuronide.
Structure
Thumb
Synonyms
ValueSource
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylateHMDB
Chemical FormulaC22H20O10
Average Molecular Weight444.392
Monoisotopic Molecular Weight444.105646844
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]1(OC2=CC3=C(C=C2)C(=O)C=C(O3)C2=CC=C(OC)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O
InChI Identifier
InChI=1S/C22H20O10/c1-29-11-4-2-10(3-5-11)15-9-14(23)13-7-6-12(8-16(13)31-15)30-22-19(26)17(24)18(25)20(32-22)21(27)28/h2-9,17-20,22,24-26H,1H3,(H,27,28)/t17-,18-,19+,20-,22+/m0/s1
InChI KeyKDULJPKZESDTFK-SXFAUFNYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • 4p-methoxyflavonoid-skeleton
  • Flavone
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • Chromone
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Methoxybenzene
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Pyranone
  • Benzenoid
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.03ALOGPS
logP0.56ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area151.98 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity107.43 m³·mol⁻¹ChemAxon
Polarizability43.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+189.56230932474
DeepCCS[M-H]-187.71730932474
DeepCCS[M-2H]-221.05130932474
DeepCCS[M+Na]+196.09630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Formononetin 7-glucuronide[H][C@@]1(OC2=CC3=C(C=C2)C(=O)C=C(O3)C2=CC=C(OC)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O5179.8Standard polar33892256
Formononetin 7-glucuronide[H][C@@]1(OC2=CC3=C(C=C2)C(=O)C=C(O3)C2=CC=C(OC)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O3929.7Standard non polar33892256
Formononetin 7-glucuronide[H][C@@]1(OC2=CC3=C(C=C2)C(=O)C=C(O3)C2=CC=C(OC)C=C2)O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O4360.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Formononetin 7-glucuronide,1TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C14135.9Semi standard non polar33892256
Formononetin 7-glucuronide,1TMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]4O)C=C3O2)C=C14134.0Semi standard non polar33892256
Formononetin 7-glucuronide,1TMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O)C=C3O2)C=C14128.9Semi standard non polar33892256
Formononetin 7-glucuronide,1TMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O[Si](C)(C)C)C=C3O2)C=C14133.6Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]4O)C=C3O2)C=C14054.9Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O)C=C3O2)C=C14037.9Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]4O[Si](C)(C)C)C=C3O2)C=C14047.3Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O)C=C3O2)C=C14016.6Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #5COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]4O[Si](C)(C)C)C=C3O2)C=C14028.4Semi standard non polar33892256
Formononetin 7-glucuronide,2TMS,isomer #6COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)C=C3O2)C=C14015.9Semi standard non polar33892256
Formononetin 7-glucuronide,3TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O)C=C3O2)C=C13989.4Semi standard non polar33892256
Formononetin 7-glucuronide,3TMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]4O[Si](C)(C)C)C=C3O2)C=C14005.7Semi standard non polar33892256
Formononetin 7-glucuronide,3TMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)C=C3O2)C=C13995.7Semi standard non polar33892256
Formononetin 7-glucuronide,3TMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)C=C3O2)C=C13981.7Semi standard non polar33892256
Formononetin 7-glucuronide,4TMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)C=C3O2)C=C13993.7Semi standard non polar33892256
Formononetin 7-glucuronide,1TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]4O)C=C3O2)C=C14434.2Semi standard non polar33892256
Formononetin 7-glucuronide,1TBDMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]4O)C=C3O2)C=C14405.4Semi standard non polar33892256
Formononetin 7-glucuronide,1TBDMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O)C=C3O2)C=C14413.2Semi standard non polar33892256
Formononetin 7-glucuronide,1TBDMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14424.9Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]4O)C=C3O2)C=C14603.6Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O)C=C3O2)C=C14580.1Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14610.7Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O)C=C3O2)C=C14556.7Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #5COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14579.4Semi standard non polar33892256
Formononetin 7-glucuronide,2TBDMS,isomer #6COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14584.1Semi standard non polar33892256
Formononetin 7-glucuronide,3TBDMS,isomer #1COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O)C=C3O2)C=C14709.6Semi standard non polar33892256
Formononetin 7-glucuronide,3TBDMS,isomer #2COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14747.3Semi standard non polar33892256
Formononetin 7-glucuronide,3TBDMS,isomer #3COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14726.9Semi standard non polar33892256
Formononetin 7-glucuronide,3TBDMS,isomer #4COC1=CC=C(C2=CC(=O)C3=CC=C(O[C@@H]4O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]4O[Si](C)(C)C(C)(C)C)C=C3O2)C=C14737.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Formononetin 7-glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 10V, Positive-QTOFsplash10-0002-0000900000-a0ca905edc8f55a1991a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 20V, Positive-QTOFsplash10-0002-0000900000-1a1573e6edc1ff12d8f32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 40V, Positive-QTOFsplash10-0udi-0001900000-631fa94ca9b41885ac632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 10V, Negative-QTOFsplash10-0006-0000900000-4d1d40649ccbae8fb1442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 20V, Negative-QTOFsplash10-004i-0000900000-7b13942858696737e9ab2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Formononetin 7-glucuronide 40V, Negative-QTOFsplash10-0006-0005900000-828424508351842599762021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101220281
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available