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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 16:58:02 UTC
Update Date2017-10-23 19:15:44 UTC
HMDB IDHMDB0060571
Secondary Accession Numbers
  • HMDB60571
Metabolite Identification
Common NameCarboxycelecoxib
DescriptionCarboxycelecoxib is a metabolite of celecoxib. Celecoxib INN is a sulfa non-steroidal anti-inflammatory drug (NSAID) and selective COX-2 inhibitor used in the treatment of osteoarthritis, rheumatoid arthritis, acute pain, painful menstruation and menstrual symptoms, and to reduce numbers of colon and rectum polyps in patients with familial adenomatous polyposis. It is marketed by Pfizer. It is known under the brand name Celebrex or Celebra for arthritis and Onsenal for polyps. Celecoxib is available by prescription in capsule form. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC17H12F3N3O4S
Average Molecular Weight411.355
Monoisotopic Molecular Weight411.050061192
IUPAC Name4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoic acid
Traditional Name4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]benzoic acid
CAS Registry NumberNot Available
SMILES
NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(C=C1)C(O)=O)C(F)(F)F
InChI Identifier
InChI=1S/C17H12F3N3O4S/c18-17(19,20)15-9-14(10-1-3-11(4-2-10)16(24)25)23(22-15)12-5-7-13(8-6-12)28(21,26)27/h1-9H,(H,24,25)(H2,21,26,27)
InChI KeyWTHNOVFEXONZMI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassAzoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Benzenesulfonamide
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzenesulfonyl group
  • Benzoyl
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Benzenoid
  • Aminosulfonyl compound
  • Sulfonyl
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alkyl halide
  • Organofluoride
  • Organohalogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility0.0032 g/LALOGPS
logP3.24ALOGPS
logP3.15ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.98ChemAxon
pKa (Strongest Basic)-0.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area115.28 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.45 m³·mol⁻¹ChemAxon
Polarizability36.17 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, Positivesplash10-00ke-0309000000-5c9efd3105d5eb76a27bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-7029400000-d1fc1a817b1e76cdb7f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0009600000-c51f5a53c7d893371dd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-0109100000-f2781f5649505037f3d8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-2195000000-23bafa8161b944732f5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0023900000-17881fe887ed5105f5a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-0039500000-f339079e0d263a263232View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-4092000000-c7b34c65678236e5072dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Celecoxib Metabolism PathwayPw000620Pw000620 greyscalePw000620 simpleNot Available
Celecoxib PathwayPw000138Pw000138 greyscalePw000138 simpleNot Available
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 IDDBMET00810
      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 Compound10047220
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available