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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:33:23 UTC
Update Date2017-12-07 04:27:31 UTC
HMDB IDHMDB0041638
Secondary Accession Numbers
  • HMDB41638
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,6S)-6-{2,3-dihydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{2,3-dihydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC(O)=C(O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)=C1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C21H22O13/c22-7-3-9(23)8-5-11(25)18(32-12(8)4-7)6-1-10(24)14(26)13(2-6)33-21-17(29)15(27)16(28)19(34-21)20(30)31/h1-4,11,15-19,21-29H,5H2,(H,30,31)/t11-,15+,16+,17-,18-,19+,21-/m1/s1
InChI KeyCQDATFYRGVZXLF-ZVHNUXTDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavonoid O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3p-o-glucuronide
  • Epigallocatechin
  • Catechin
  • Hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenol ether
  • Phenoxy compound
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Phenol
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Polyol
  • Ether
  • Acetal
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

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 Solubility3.49 g/LALOGPS
logP0.41ALOGPS
logP-0.46ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.86ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area226.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.99 m³·mol⁻¹ChemAxon
Polarizability44.85 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, Positivesplash10-06vi-8109500000-635e213721c2e31d01f4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-7200029000-07602fa50e2fc9a87b75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0635900000-9550ca72a5ac93dd6b9fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0933100000-ed0c66633f5f018ec146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00g0-0900000000-63de44e405facf445f7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0540-1313900000-4b3afce8f3a3267fd20bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2938500000-4c850a14c0329593741cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-2913000000-3b40b7cc56e025f983d9View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 786 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 ID786
    FoodDB IDFDB029793
    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 ]