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Record Information
Version4.0
Creation Date2012-09-12 03:33:28 UTC
Update Date2017-09-27 08:33:33 UTC
HMDB IDHMDB0041639
Secondary Accession Numbers
  • HMDB41639
Metabolite Identification
Common Name(-)-Epigallocatechin 3-glucuronide
Description(-)-Epigallocatechin 3-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).
Structure
Thumb
Synonyms
ValueSource
(-)-Epigallocatechin 3-O-glucuronideHMDB
Chemical FormulaC21H22O13
Average Molecular Weight482.3916
Monoisotopic Molecular Weight482.10604079
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](O[C@@H]2CC3=C(O[C@@H]2C2=CC(O)=C(O)C(O)=C2)C=C(O)C=C3O)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C21H22O13/c22-7-3-9(23)8-5-13(33-21-17(29)15(27)16(28)19(34-21)20(30)31)18(32-12(8)4-7)6-1-10(24)14(26)11(25)2-6/h1-4,13,15-19,21-29H,5H2,(H,30,31)/t13-,15+,16+,17-,18-,19+,21-/m1/s1
InChI KeyZTOAOZDTXSRHIB-BBGDWMAASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavonoid-3-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3-o-glucuronide
  • Epigallocatechin
  • Flavonoid-3-o-glycoside
  • Catechin
  • Flavan-3-ol
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Flavan
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzenetriol
  • Pyrogallol derivative
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Phenol
  • Monosaccharide
  • Hydroxy acid
  • Pyran
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Acetal
  • Polyol
  • Ether
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.7 g/LALOGPS
logP1.05ALOGPS
logP0.041ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area226.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.26 m³·mol⁻¹ChemAxon
Polarizability43.99 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0bt9-9106300000-552f6ab3cff61b7abb97View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-3372129000-3f8dcfea2d221f87f6eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0914600000-c39b886d397274aa8aabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-059i-0922000000-4de1b6b85fd8744dc69fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-1900000000-4cf9036d71c53dacf819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-1304900000-446f5d442ea29d91a350View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2729500000-01d07573e50e75351131View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3913000000-25aa7776faf06e9d1e6dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 780 details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite ID780
    FoodDB IDFDB029794
    KNApSAcK IDNot Available
    Chemspider IDNot Available
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem CompoundNot Available
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]