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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:07:01 UTC
Update Date2018-05-20 20:31:27 UTC
HMDB IDHMDB0060915
Secondary Accession Numbers
  • HMDB60915
Metabolite Identification
Common NameDiclofenac acyl glucuronide
DescriptionDiclofenac acyl glucuronide is a metabolite of diclofenac. Diclofenac is a non-steroidal anti-inflammatory drug (NSAID) taken to reduce inflammation and as an analgesic reducing pain in certain conditions. The name is derived from its chemical name: 2-(2,6-dichloranilino) phenylacetic acid. In the United Kingdom, India, Brazil and the United States, it may be supplied as either the sodium or potassium salt, in China most often as the sodium salt, while in some other countries only as the potassium salt. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
Diclofenac acyl glucuronideChEBI
Diclofenac glucuronideChEBI
Diclofenac b-D-glucosiduronateGenerator
Diclofenac b-D-glucosiduronic acidGenerator
Diclofenac beta-D-glucosiduronateGenerator
Diclofenac β-D-glucosiduronateGenerator
Diclofenac β-D-glucosiduronic acidGenerator
1-O-(2-((2',6'-Dichlorophenyl)amino)phenylacetyl)glucopyranuronic acidMeSH
D-1-O-g CPDMeSH
Diclofenac 1-O-acyl glucuronideMeSH
Chemical FormulaC20H19Cl2NO8
Average Molecular Weight472.273
Monoisotopic Molecular Weight471.048772003
IUPAC Name(2S,3S,4S,5R,6S)-6-[(2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Namediclofenac acyl glucuronide
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CC=CC=C2NC2=C(Cl)C=CC=C2Cl)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C20H19Cl2NO8/c21-10-5-3-6-11(22)14(10)23-12-7-2-1-4-9(12)8-13(24)30-20-17(27)15(25)16(26)18(31-20)19(28)29/h1-7,15-18,20,23,25-27H,8H2,(H,28,29)/t15-,16-,17+,18-,20+/m0/s1
InChI KeyJXIKYYSIYCILNG-HBWRTXEVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Hexose monosaccharide
  • Aniline or substituted anilines
  • 1,3-dichlorobenzene
  • Beta-hydroxy acid
  • Chlorobenzene
  • Halobenzene
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Pyran
  • Hydroxy acid
  • Oxane
  • Monosaccharide
  • Aryl halide
  • Aryl chloride
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Secondary amine
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organohalogen compound
  • Amine
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility0.36 g/LALOGPS
logP2.87ALOGPS
logP2.31ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.23ChemAxon
pKa (Strongest Basic)-2.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.55 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.76 m³·mol⁻¹ChemAxon
Polarizability43.39 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0udi-6290100000-11854529ec38c657d635View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-1090000000-91e19184ba80bfa444c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fba-0390400000-d3adfc41891a42479977View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-0390000000-e432d1f60b17333d90a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufs-3590000000-d9155687eed169128d83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190300000-2b9383e1b547fd3172d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-2590100000-73a47a825b490b4a35c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-6490000000-0bce10ee218cee4b866eView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
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 Compound16084218
      PDB IDNot Available
      ChEBI ID59609
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Kenny JR, Maggs JL, Meng X, Sinnott D, Clarke SE, Park BK, Stachulski AV: Syntheses and characterization of the acyl glucuronide and hydroxy metabolites of diclofenac. J Med Chem. 2004 May 20;47(11):2816-25. [PubMed:15139759 ]
      2. Scialis RJ, Manautou JE: Elucidation of the Mechanisms through Which the Reactive Metabolite Diclofenac Acyl Glucuronide Can Mediate Toxicity. J Pharmacol Exp Ther. 2016 Apr;357(1):167-76. doi: 10.1124/jpet.115.230755. Epub 2016 Feb 11. [PubMed:26869668 ]