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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uy0-0729000000-75ddea9acd30a029b25bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0aou-3960000000-2bd7d8539498dde5c2f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-001i-0029000000-1a5ed66ff895eeb127ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0129000000-a967b7f9e88a461e3db4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01q9-2598000000-f71f4f9eb7c83ddf79f4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-001i-0029000000-13ff69b3abd31dde6baeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-014i-9100000000-9a8cd0b75d276f108651View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-41eaecd214cbc50e645eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-f2376e3bc87d5951988cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-02vi-9100000000-3b8e53549d02c7db5cbaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-014i-9220000000-e1d41283ce6235c1de0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0gx0-0059000000-9e48db23da1b4b859e68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-001i-0009000000-25406fbf853a86a41e2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-016r-7292000000-0c298e1f9b51823232c7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-57c7836793a5363fda3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-017j-0198000000-927a7c09840b934e4ceaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-e3bce1b4f36e339f9f39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-001i-0293000000-c8b94b6bd1da23395b78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-001i-0009000000-72b8641321f8f9f0f2b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-0490000000-0b6fde7d96dea087de34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-23d25f88a0e277e47c54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0009000000-a933645e1cf7fb8edf4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ufr-3289000000-7c03de47cb9bd124fa0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0009000000-9d1a9c471dc123cee735View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0009000000-bdb3f0787c9e831e7530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9125000000-ad5803f68fece8f76b2aView in MoNA
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