You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2013-06-12 17:33:17 UTC
Update Date2016-02-11 08:08:04 UTC
HMDB IDHMDB60545
Secondary Accession NumbersNone
Metabolite Identification
Common NameO-Desmethylindomethacin
DescriptionO-Desmethylindomethacin is a metaboite of Indomethacin. Indomethacin is metabolized in humans by O-demethylation, and by acyl glucuronidation to the 1-O-glucuronide. Indomethacin and O-desmethylindomethacin may be glucuronidated in the kidney. Probenecid is a known substrate for renal glucuronidation. If indomethacin is glucuronidated in the human kidney like probenecid, then this glucuronidation might be reduced or inhibited under probenecid co-medication. (PMID: 8156046 )
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H14ClNO4
Average Molecular Weight343.761
Monoisotopic Molecular Weight343.061135648
IUPAC Name2-[1-(4-chlorobenzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]acetic acid
Traditional Name[1-(4-chlorobenzoyl)-5-hydroxy-2-methylindol-3-yl]acetic acid
CAS Registry NumberNot Available
SMILES
CC1=C(CC(O)=O)C2=C(C=CC(O)=C2)N1C(=O)C1=CC=C(Cl)C=C1
InChI Identifier
InChI=1/C18H14ClNO4/c1-10-14(9-17(22)23)15-8-13(21)6-7-16(15)20(10)18(24)11-2-4-12(19)5-3-11/h2-8,21H,9H2,1H3,(H,22,23)
InChI KeyInChIKey=KMLNWQPYFBIALN-UHFFFAOYNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassBenzoylindoles
Direct ParentBenzoylindoles
Alternative Parents
Substituents
  • Benzoylindole
  • Indole-3-acetic acid derivative
  • Indolyl carboxylic acid derivative
  • Indolecarboxylic acid derivative
  • Hydroxyindole
  • 4-halobenzoic acid or derivatives
  • Indole
  • Benzoic acid or derivatives
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Substituted pyrrole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Pyrrole
  • Carboxamide group
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.015 mg/mLALOGPS
logP3.59ALOGPS
logP3.38ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.53 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity90.33 m3·mol-1ChemAxon
Polarizability34.44 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00156
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
NuGOwiki LinkHMDB60545
Metagene LinkHMDB60545
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