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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-08 14:59:00 UTC
Update Date2017-12-07 02:55:46 UTC
HMDB IDHMDB0029181
Secondary Accession Numbers
  • HMDB29181
Metabolite Identification
Common Name4'-O-methyl-(-)-epicatechin-5-O-beta-glucuronide
Description4'-o-methyl-(-)-epicatechin-5-o-beta-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. 4'-o-methyl-(-)-epicatechin-5-o-beta-glucuronide is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 4'-o-methyl-(-)-epicatechin-5-o-beta-glucuronide can be found primarily in blood and urine, as well as in human kidney and liver tissues. 4'-O-methyl-(-)-epicatechin-5-O-beta-glucuronide is a cocoa metabolite from gut microflora. It is found n urine..
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H26O11
Average Molecular Weight478.4459
Monoisotopic Molecular Weight478.147511674
IUPAC Name(3S,4S,6S)-6-{[(3S)-2-(4-ethyl-3-hydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(3S,4S,6S)-6-{[(3S)-2-(4-ethyl-3-hydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CCC1=CC=C(C=C1O)C1OC2=CC(O)=CC(O[C@@H]3OC([C@@H](O)[C@H](O)C3O)C(O)=O)=C2C[C@@H]1O
InChI Identifier
InChI=1S/C23H26O11/c1-2-9-3-4-10(5-13(9)25)20-14(26)8-12-15(32-20)6-11(24)7-16(12)33-23-19(29)17(27)18(28)21(34-23)22(30)31/h3-7,14,17-21,23-29H,2,8H2,1H3,(H,30,31)/t14-,17-,18-,19?,20?,21?,23+/m0/s1
InChI KeyMUYXNRKLXILZTM-QHZMYPFFSA-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-5-o-glucuronide
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavan-3-ol
  • Hydroxyflavonoid
  • Flavan
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Beta-hydroxy acid
  • Hydroxy acid
  • Pyran
  • Monocyclic benzene moiety
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Secondary alcohol
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

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 Solubility1.59 g/LALOGPS
logP1.01ALOGPS
logP1.11ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.93ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area186.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.67 m³·mol⁻¹ChemAxon
Polarizability47.23 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, Positivesplash10-0bvr-9207600000-ac03f1fb120a39fa9736View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00c0-2231119000-8ce5d482409fece51721View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w4r-0366900000-1705800f56e6f685f651View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0954100000-b15b3a0ed647247b531fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0910000000-1a128b8365132c32c8e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fc0-1213900000-daaea4d3aa7b0aeb566aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2927500000-b3bee0c2c8b8456eaa25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ufr-3924000000-57aa5a6f93068ac8275eView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      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 ReferencesNot Available