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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:01 UTC
HMDB IDHMDB0015565
Secondary Accession Numbers
  • HMDB15565
Metabolite Identification
Common NameEtoricoxib
DescriptionEtoricoxib, also known as L791456 or MK-663, belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other. Etoricoxib is a drug which is used for the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. In humans, etoricoxib is involved in the etoricoxib action pathway. Etoricoxib is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on Etoricoxib.
Structure
Data?1582753311
Synonyms
ValueSource
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulfonyl)phenyl)pyridineChEBI
5-Chloro-3-(4-methanesulfonyl-phenyl)-6'-methyl-[2,3']bipyridinylChEBI
5-Chloro-6'-methyl-3-(p-(methylsulfonyl)phenyl)-2,3'-bipyridineChEBI
EtoricoxibumChEBI
L791456ChEBI
5-Chloro-2-(6-methylpyridin-3-yl)-3-(4-(methylsulphonyl)phenyl)pyridineGenerator
5-Chloro-3-(4-methanesulphonyl-phenyl)-6'-methyl-[2,3']bipyridinylGenerator
5-Chloro-6'-methyl-3-(p-(methylsulphonyl)phenyl)-2,3'-bipyridineGenerator
MK-663HMDB
ArcoxiaHMDB
Chemical FormulaC18H15ClN2O2S
Average Molecular Weight358.842
Monoisotopic Molecular Weight358.054276131
IUPAC Name5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
Traditional Nameetoricoxib
CAS Registry Number202409-33-4
SMILES
CC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O
InChI Identifier
InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
InChI KeyMNJVRJDLRVPLFE-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassBipyridines and oligopyridines
Direct ParentBipyridines and oligopyridines
Alternative Parents
Substituents
  • Bipyridine
  • 3-phenylpyridine
  • Benzenesulfonyl group
  • Methylpyridine
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Sulfone
  • Sulfonyl
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0033 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP3.7ALOGPS
logP2.79ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)19.69ChemAxon
pKa (Strongest Basic)4.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area59.92 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.04 m³·mol⁻¹ChemAxon
Polarizability36.42 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+185.99930932474
DeepCCS[M-H]-183.64130932474
DeepCCS[M-2H]-217.53630932474
DeepCCS[M+Na]+192.76330932474
AllCCS[M+H]+182.532859911
AllCCS[M+H-H2O]+179.332859911
AllCCS[M+NH4]+185.532859911
AllCCS[M+Na]+186.432859911
AllCCS[M-H]-180.932859911
AllCCS[M+Na-2H]-180.632859911
AllCCS[M+HCOO]-180.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
EtoricoxibCC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O4444.7Standard polar33892256
EtoricoxibCC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O3145.9Standard non polar33892256
EtoricoxibCC1=NC=C(C=C1)C1=C(C=C(Cl)C=N1)C1=CC=C(C=C1)S(C)(=O)=O3209.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Etoricoxib GC-MS (Non-derivatized) - 70eV, Positivesplash10-00c3-1195000000-a6512b3342a7ab34b5392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etoricoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Etoricoxib GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 10V, Positive-QTOFsplash10-0a4i-0009000000-f7a7b2b391bf2c553bee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 20V, Positive-QTOFsplash10-0a4i-0019000000-ee3806388a3685ebb2ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 40V, Positive-QTOFsplash10-014l-1093000000-f6befa9e036305228b8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 10V, Negative-QTOFsplash10-0a4i-0009000000-50b1220eaafc5cd21ae92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 20V, Negative-QTOFsplash10-0a4i-0019000000-7f9d7c868b2e84a344d82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 40V, Negative-QTOFsplash10-004i-7193000000-02c1e0800c4c34dc46272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 10V, Positive-QTOFsplash10-0a4i-0009000000-fa58affcccc87c3233cb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 20V, Positive-QTOFsplash10-0a4i-0009000000-dcccff10c50c0a3a450b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 40V, Positive-QTOFsplash10-00pr-1092000000-eccb7f42163f67d408a92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 10V, Negative-QTOFsplash10-0a4i-0009000000-6292d183612a368493ec2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 20V, Negative-QTOFsplash10-053r-9005000000-b2f21f92017e3512dfc22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Etoricoxib 40V, Negative-QTOFsplash10-0059-9030000000-9d3d76f515503b2f8eba2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01628 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01628 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01628
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110209
KEGG Compound IDC11718
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEtoricoxib
METLIN IDNot Available
PubChem Compound123619
PDB IDNot Available
ChEBI ID6339
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available