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Kaempferol 3-glucuronide (FDB000634)

Record Information
Version1.0
Creation date2010-04-08 22:04:39 UTC
Update date2020-02-24 19:10:11 UTC
Primary IDFDB000634
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameKaempferol 3-glucuronide
DescriptionKaempferol 3-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-glucuronide is found, on average, in the highest concentration within a few different foods, such as endives (Cichorium endivia), tropical highland blackberries (Rubus adenotrichos), and blackberries (Rubus) and in a lower concentration in red raspberries (Rubus idaeus), common beans (Phaseolus vulgaris), and strawberries (Fragaria X ananassa). Kaempferol 3-glucuronide has also been detected, but not quantified in, several different foods, such as mung beans (Vigna radiata), chicories (Cichorium intybus), yellow wax beans (Phaseolus vulgaris), lettuces (Lactuca sativa), and dills (Anethum graveolens). This could make kaempferol 3-glucuronide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Kaempferol 3-glucuronide.
CAS Number22688-78-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
Polarizability42.39 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H18O12
IUPAC name6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=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)
InChI KeyFNTJVYCFNVUBOL-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C(OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)OC(C1O)C(O)=O
Average Molecular Weight462.3604
Monoisotopic Molecular Weight462.07982604
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Foods
  • Cocoa and cocoa products

    • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateNot Available
    Physical DescriptionNot Available
    Mass CompositionC 54.55%; H 3.92%; O 41.52%DFC
    Melting PointMp 189-190.5°DFC
    Boiling PointNot Available
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    Predicted GC-MSKaempferol 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4l-9105200000-d004a17186cb587e7dc2Spectrum
    Predicted GC-MSKaempferol 3-glucuronide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-4221119000-f2ac019daca3c701e092Spectrum
    Predicted GC-MSKaempferol 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_20, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_3_31, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_3_33, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_4_33, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, "Kaempferol 3-glucuronide,2TMS,#20" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSKaempferol 3-glucuronide, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - 6V, Negativesplash10-000i-0190100000-9fb3c360adb8bceb1aad2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0090000000-c2e29d689f1b1f5536182021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01p9-0190500000-a420056171bccd29714a2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0190000000-5f5d494914074a8876832021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01p9-0090400000-d5d70cd9aa29b024532b2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0190100000-be5a5766370789a8bc842021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0090000000-daa9a58ee091e1b7989d2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-056r-1950000000-f9d19c49a98d6c343eba2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0190100000-d7cd9684603d21457f002021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0190000000-509744321912fc0235882021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0290000000-553455edaf7f08ce5d512021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-06ri-1940000000-b146e97833ee4a5ac8da2021-09-20View Spectrum
    MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-01p9-0190400000-fd15e974db1fac2b045f2021-09-20View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0170900000-1e4e727a77229b6993eb2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090100000-404ced678a3392b5aa5c2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2590000000-d78ceaa8baa9bf67cd332015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0170900000-1e4e727a77229b6993eb2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090100000-404ced678a3392b5aa5c2015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-2590000000-d78ceaa8baa9bf67cd332015-04-24View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-1141900000-2de4c77a59276fcc79f42015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2191200000-821a7aa34257929af4692015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3490000000-03573ca62c35318e42682015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-1141900000-2de4c77a59276fcc79f42015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2191200000-821a7aa34257929af4692015-04-25View Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3490000000-03573ca62c35318e42682015-04-25View Spectrum
    NMRNot Available
    ChemSpider ID11500908
    ChEMBL IDNot Available
    KEGG Compound IDNot Available
    Pubchem Compound ID14185731
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID305
    DrugBank IDNot Available
    HMDB IDHMDB29500
    CRC / DFC (Dictionary of Food Compounds) IDODZ15-T:BFH03-D
    EAFUS IDNot Available
    Dr. Duke IDKAEMPFEROL-3-O-BETA-D-GLUCURONIDE|KAEMPFEROL-3-GLUCURONIDE
    BIGG IDNot Available
    KNApSAcK IDC00005141
    HET IDNot Available
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSBFG98-E:BFH03-D
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    Enzymes
    NameGene NameUniProt ID
    UDP-glucuronosyltransferase 2B4UGT2B4P06133
    UDP-glucuronosyltransferase 1-4UGT1A4P22310
    UDP-glucuronosyltransferase 2B7UGT2B7P16662
    UDP-glucuronosyltransferase 1-1UGT1A1P22309
    UDP-glucuronosyltransferase 1-9UGT1A9O60656
    UDP-glucuronosyltransferase 1-6UGT1A6P19224
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.