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Record Information
Version3.6
Creation Date2012-09-12 03:38:55 UTC
Update Date2017-08-18 04:00:44 UTC
HMDB IDHMDB0041729
Secondary Accession Numbers
  • HMDB41729
Metabolite Identification
Common Name(-)-Epicatechin 7-O-glucuronide
Description(-)-Epicatechin 7-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).
Structure
Thumb
Synonyms
ValueSource
Epicatechin 7-O-glucuronideHMDB
Chemical FormulaC21H22O12
Average Molecular Weight466.3922
Monoisotopic Molecular Weight466.111126168
IUPAC Name(2S,3S,4S,5R,6S)-6-{[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C(O)=C1)C=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C2O
InChI Identifier
InChI=1S/C21H22O12/c22-10-2-1-7(3-12(10)24)18-13(25)6-9-11(23)4-8(5-14(9)32-18)31-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,13,15-19,21-28H,6H2,(H,29,30)/t13-,15+,16+,17-,18-,19+,21-/m1/s1
InChI KeyFDWDKTKDGDLDTP-BBGDWMAASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassFlavonoids
Direct ParentFlavonoid-7-O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-7-o-glucuronide
  • Flavonoid-7-o-glycoside
  • Catechin
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Beta-hydroxy acid
  • Phenol
  • Monosaccharide
  • Monocyclic benzene moiety
  • Pyran
  • Hydroxy acid
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Food
Biofunction
  • Nutrient
  • Waste products
Application
  • Nutrient
Cellular locations
  • Cytoplasm
  • Extracellular
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 Solubility2.68 mg/mLALOGPS
logP0.04ALOGPS
logP-0.15ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.01 m3·mol-1ChemAxon
Polarizability43.94 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      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 ID785
      FoodDB IDFDB029895
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      NuGOwiki LinkHMDB0041729
      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 ]