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Record Information
Version3.6
Creation Date2012-09-08 14:58:30 UTC
Update Date2016-02-11 01:36:15 UTC
HMDB IDHMDB29164
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-epicatechin-3'-O-glucuronide
Description(-)-Epicatechin-3'-O-glucuronide is a cocoa metabolite from gut microflora. It is found in urine.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H24O11
Average Molecular Weight452.4087
Monoisotopic Molecular Weight452.13186161
IUPAC Name(3S)-2-(4-hydroxy-3-{[(3S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
Traditional Name(3S)-2-(4-hydroxy-3-{[(3S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2=CC(=CC=C2O)C2OC3=CC(O)=CC(O)=C3C[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C21H24O11/c22-7-16-17(27)18(28)19(29)21(32-16)31-15-3-8(1-2-11(15)24)20-13(26)6-10-12(25)4-9(23)5-14(10)30-20/h1-5,13,16-29H,6-7H2/t13-,16?,17+,18-,19-,20?,21?/m0/s1
InChI KeyInChIKey=ZZTOVZGFHZQEAT-JUZNXHDUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid o-glycosides. These are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid o-glycoside
  • Flavonoid-3p-o-glycoside
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Resorcinol
  • Phenol ether
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Saccharide
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
OriginNot Available
Biofunction
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.17 mg/mLALOGPS
logP-0.56ALOGPS
logP-0.47ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)9.26ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.14 m3·mol-1ChemAxon
Polarizability43.52 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
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 IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB29164
Metagene LinkHMDB29164
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available