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Record Information
Version4.0
Creation Date2013-07-09 16:07:25 UTC
Update Date2017-09-27 08:43:57 UTC
HMDB IDHMDB0060922
Secondary Accession Numbers
  • HMDB60922
Metabolite Identification
Common NameIndomethacin acyl glucuronide
DescriptionIndomethacin acyl glucuronide is a metabolite of indomethacin. Indometacin or indomethacin (USAN and former BAN) is a non-steroidal anti-inflammatory drug (NSAID) commonly used as a prescription medication to reduce fever, pain, stiffness, and swelling. It works by inhibiting the production of prostaglandins, molecules known to cause these symptoms. It is marketed under more than seventy different trade names. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H24ClNO10
Average Molecular Weight533.912
Monoisotopic Molecular Weight533.1088737
IUPAC Name(2S,3S,4S,5R,6S)-6-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=C1)N(C(=O)C1=CC=C(Cl)C=C1)C(C)=C2CC(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C25H24ClNO10/c1-11-15(10-18(28)36-25-21(31)19(29)20(30)22(37-25)24(33)34)16-9-14(35-2)7-8-17(16)27(11)23(32)12-3-5-13(26)6-4-12/h3-9,19-22,25,29-31H,10H2,1-2H3,(H,33,34)/t19-,20-,21+,22-,25+/m0/s1
InChI KeyQCBWEVBGELGABM-CZLVRFMKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassIndoles and derivatives
Direct ParentBenzoylindoles
Alternative Parents
Substituents
  • Benzoylindole
  • 1-o-glucuronide
  • O-glucuronide
  • Indole-3-acetic acid derivative
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Indolecarboxylic acid derivative
  • 3-alkylindole
  • Halobenzoic acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Indole
  • Benzoic acid or derivatives
  • Anisole
  • Benzoyl
  • Beta-hydroxy acid
  • Chlorobenzene
  • Halobenzene
  • Alkyl aryl ether
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Aryl halide
  • Aryl chloride
  • Benzenoid
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Acetal
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

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 Solubility0.065 g/LALOGPS
logP2.25ALOGPS
logP1.58ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity127.11 m³·mol⁻¹ChemAxon
Polarizability52.5 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00157
      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
      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