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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:42:47 UTC
Update Date2017-12-07 04:28:44 UTC
HMDB IDHMDB0041786
Secondary Accession Numbers
  • HMDB41786
Metabolite Identification
Common NameUrolithin A 3,8-O-diglucuronide
DescriptionUrolithin A 3,8-O-diglucuronide is a polyphenol metabolite detected in biological fluids (PMID: 20428313 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H24O16
Average Molecular Weight580.4485
Monoisotopic Molecular Weight580.10643472
IUPAC Name(2S,3S,4S,5R,6S)-6-[(8-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxo-6H-benzo[c]chromen-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[(8-{[(2S,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-6-oxobenzo[c]chromen-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CC3=C(C=C2)C2=C(C=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C2)C(=O)O3)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C25H24O16/c26-13-15(28)19(21(32)33)40-24(17(13)30)37-7-1-3-9-10-4-2-8(6-12(10)39-23(36)11(9)5-7)38-25-18(31)14(27)16(29)20(41-25)22(34)35/h1-6,13-20,24-31H,(H,32,33)(H,34,35)/t13-,14-,15-,16-,17+,18+,19-,20-,24+,25+/m0/s1
InChI KeySXMJSEFKPOZNAT-ILJCXFEASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Coumarin
  • Isocoumarin
  • O-glycosyl compound
  • 2-benzopyran
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Beta-hydroxy acid
  • Pyran
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • 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 Solubility2.25 g/LALOGPS
logP-0.41ALOGPS
logP-1.6ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)2.82ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area259.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity124.92 m³·mol⁻¹ChemAxon
Polarizability53.26 ųChemAxon
Number of Rings5ChemAxon
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, Positivesplash10-03fr-2100930000-3944ff938116a09a1990View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0012-8640697000-4069a3eaeda0a45b8201View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06ri-0019580000-fca41eba40393032d079View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-0095200000-25e124985eb0a036aa78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0192000000-ece3b8edcb3369db327dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9i-0113590000-5e54bf3d864cfbf9681fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1139760000-d5a73af30ed9ad3b83e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-3198400000-ce11d8f90b287f828324View 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 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 ID1035
      FoodDB IDFDB029961
      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 ]