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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:38:51 UTC
Update Date2017-12-07 04:28:13 UTC
HMDB IDHMDB0041728
Secondary Accession Numbers
  • HMDB41728
Metabolite Identification
Common Name(-)-Epicatechin 3'-O-glucuronide
Description(-)-epicatechin 3'-o-glucuronide is a member of the class of compounds known as flavonoid o-glucuronides. Flavonoid o-glucuronides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid (-)-epicatechin 3'-o-glucuronide is slightly soluble (in water) and a weakly acidic compound (based on its pKa) (-)-epicatechin 3'-o-glucuronide can be found primarily in blood and urine, as well as in human kidney and liver tissues. Within the cell, (-)-epicatechin 3'-o-glucuronide is primarily located in the cytoplasm. It can also be found in the extracellular space (-)-Epicatechin 3'-O-glucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 )..
Structure
Thumb
Synonyms
ValueSource
Epicatechin 3'-O-glucuronideHMDB
Chemical FormulaC21H22O12
Average Molecular Weight466.3922
Monoisotopic Molecular Weight466.111126168
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{2-hydroxy-5-[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1CC2=C(O[C@@H]1C1=CC=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/C21H22O12/c22-8-4-11(24)9-6-12(25)18(31-13(9)5-8)7-1-2-10(23)14(3-7)32-21-17(28)15(26)16(27)19(33-21)20(29)30/h1-5,12,15-19,21-28H,6H2,(H,29,30)/t12-,15+,16+,17-,18-,19+,21-/m1/s1
InChI KeyBUONZQIZWIITTB-CVPXIJHMSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonoid o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glucuronides
Alternative Parents
Substituents
  • Flavonoid-3p-o-glucuronide
  • Catechin
  • Hydroxyflavonoid
  • Flavan-3-ol
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Chromane
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Phenol
  • Pyran
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Secondary alcohol
  • Acetal
  • Polyol
  • Ether
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

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 Solubility2.89 g/LALOGPS
logP0.08ALOGPS
logP-0.15ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.01 m³·mol⁻¹ChemAxon
Polarizability42.32 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, Positivesplash10-054k-9108500000-11fc73b483920ad69445View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-7200029000-8ed5a427129980dfbe90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rg-0690800000-1545d8c57f3e28f4a41eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007c-0970100000-467fb1b9e89f4d4e2654View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0910000000-d139ac043424be2eebb3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-1340900000-f16fa20f169f9fd80f39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2891400000-d53ae30092c98483fff9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2930000000-3421cc335bec124835c0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 768 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029894
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76969982
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 ]