Showing metabocard for Celecoxib (BMDB0005014)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:14:38 UTC
Update Date2020-04-22 15:15:07 UTC
BMDB IDBMDB0005014
Secondary Accession Numbers
  • BMDB05014
Metabolite Identification
Common NameCelecoxib
DescriptionCelecoxib, also known as celebrex or onsenal, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. Celecoxib is an extremely weak basic (essentially neutral) compound (based on its pKa). Celecoxib is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CelebrexChEBI
CelecoxibumChEBI
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulfonamideChEBI
OnsenalKegg
p-(5-p-Tolyl-3-(trifluoromethyl)pyrazol-1-yl)benzenesulphonamideGenerator
CelocoxibHMDB
4-(5-(4-Methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamideHMDB
Chemical FormulaC17H14F3N3O2S
Average Molecular Weight381.372
Monoisotopic Molecular Weight381.075882012
IUPAC Name4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzene-1-sulfonamide
Traditional Namecelecoxib
CAS Registry Number169590-42-5
SMILES
CC1=CC=C(C=C1)C1=CC(=NN1C1=CC=C(C=C1)S(N)(=O)=O)C(F)(F)F
InChI Identifier
InChI=1S/C17H14F3N3O2S/c1-11-2-4-12(5-3-11)15-10-16(17(18,19)20)22-23(15)13-6-8-14(9-7-13)26(21,24)25/h2-10H,1H3,(H2,21,24,25)
InChI KeyRZEKVGVHFLEQIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Toluene
  • Monocyclic benzene moiety
  • Organosulfonic acid amide
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Alkyl halide
  • Alkyl fluoride
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point101.7 - 103.9 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.99ALOGPS
logP4.01ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)10.7ChemAxon
pKa (Strongest Basic)-0.42ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.23 m³·mol⁻¹ChemAxon
Polarizability35.2 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005014
DrugBank IDDB00482
Phenol Explorer Compound IDNot Available
FooDB IDFDB023586
KNApSAcK IDNot Available
Chemspider ID2562
KEGG Compound IDC07589
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCelecoxib
METLIN IDNot Available
PubChem Compound2662
PDB IDNot Available
ChEBI ID41423
References
Synthesis ReferenceTalley, John J.; Penning, Thomas D.; Collins, Paul W.; Rogier, Donald J., Jr.; Malecha, James W.; Miyashiro, Julie M.; Bertenshaw, Stephen R.; Khanna, Ish K.; Granets, Matthew J.; et al. Preparation of pyrazolylbenzenesulfonamides as antiinflammatories. PCT Int. Appl. (1995), 254 pp. CODEN: PIXXD2 WO 9515316 A1 19950608 CAN 123:340112 AN 1995:931246
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available