Kaempferol 3-O-glucuronide (YMDB01724)

Identification
YMDB IDYMDB01724
NameKaempferol 3-O-glucuronide
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionKaempferol 3-O-glucuronide belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position. Kaempferol 3-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Kaempferol 3-O-glucuronide may be a unique S. cerevisiae (yeast) metabolite.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
CAS number22688-78-4
WeightAverage: 462.3604
Monoisotopic: 462.07982604
InChI KeyFNTJVYCFNVUBOL-MBIBTLSJSA-N
InChIInChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14-,15-,16+,19-,21?/m0/s1
IUPAC Name(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name(2S,3S,4S,5R)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Chemical FormulaC21H18O12
SMILESO[C@@H]1[C@@H](O)C(OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C2=CC=C(O)C=C2)O[C@@H]([C@H]1O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-3-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3-o-glucuronide
  • Flavonoid-3-o-glycoside
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Beta-hydroxy acid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.96 g/LALOGPS
logP1.4ALOGPS
logP0.48ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)2.71ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.16 m³·mol⁻¹ChemAxon
Polarizability42.63 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-1141900000-a6cb1a514403d46cc1c0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1191200000-fc0c16f367ae3913999dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3490000000-3e785606fb50daf90ea1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01pa-0180900000-2f155fc6e5f60b1d21b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190100000-46e0773d6b10b61ddf41JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2590000000-c2fdc8ee2f5a450835e2JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID22846027
Kegg IDNot Available
ChemSpider ID24844586
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available