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Record Information
Version3.6
Creation Date2013-07-22 19:49:56 UTC
Update Date2017-03-02 22:05:46 UTC
HMDB IDHMDB61132
Secondary Accession NumbersNone
Metabolite Identification
Common NameCelecoxib glucuronide
DescriptionCelecoxib glucuronide is a metabolite of celecoxib. Celecoxib 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 FormulaC22H20F3N3O9S
Average Molecular Weight559.469
Monoisotopic Molecular Weight559.087234558
IUPAC Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{4-[1-(4-sulfamoylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S)-3,4,5-trihydroxy-6-{4-[2-(4-sulfamoylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
NS(=O)(=O)C1=CC=C(C=C1)N1N=C(C=C1C1=CC=C(OC2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C=C1)C(F)(F)F
InChI Identifier
InChI=1S/C22H20F3N3O9S/c23-22(24,25)15-9-14(28(27-15)11-3-7-13(8-4-11)38(26,34)35)10-1-5-12(6-2-10)36-21-18(31)16(29)17(30)19(37-21)20(32)33/h1-9,16-19,21,29-31H,(H,32,33)(H2,26,34,35)/t16-,17-,18+,19-,21?/m1/s1
InChI KeyBMBHPAUFWUKYDR-AVPDHNOJSA-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
  • Phenylpyrazole
  • O-glycosyl compound
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Organosulfonic acid amide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Pyran
  • Azole
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Pyrazole
  • Secondary alcohol
  • Polyol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Alkyl halide
  • Organosulfur compound
  • Organopnictogen compound
  • Alkyl fluoride
  • Organohalogen compound
  • Organofluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 Solubility0.053 mg/mLALOGPS
logP2.04ALOGPS
logP1.24ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-0.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area194.43 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity121.19 m3·mol-1ChemAxon
Polarizability49.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDDBMET00813
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 LinkHMDB61132
Metagene LinkHMDB61132
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