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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:01 UTC
Update Date2021-09-14 15:07:05 UTC
HMDB IDHMDB0041920
Secondary Accession Numbers
  • HMDB41920
Metabolite Identification
Common NameLoxoprofen
DescriptionAs most NSAIDs, loxoprofen is a non-selective cyclooxygenase inhibitor, and works by reducing the synthesis of prostaglandins from arachidonic acid. Loxoprofen (INN) is a non-steroidal anti-inflammatory drug in the propionic acid derivatives group, which also includes ibuprofen and naproxen among others. It is marketed in Brazil, Mexico and Japan by Sankyo as its sodium salt, loxoprofen sodium, under the trade name Loxonin, Argentina as Oxeno and in India as Loxomac. It is available in these countries for oral administration, and a transdermal preparation was approved for sale in Japan on January 2006. Loxoprofen is a prodrug. It is quickly converted to its active trans-alcohol metabolite following oral administration, and reaches its peak plasma concentration within 30 to 50 minutes.
Structure
Data?1563863714
Synonyms
ValueSource
(+-)-((2-Oxocyclopentyl)methyl)hydratropic acidChEBI
LoxoprofeneChEBI
LoxoprofenoChEBI
LoxoprofenumChEBI
(+-)-((2-Oxocyclopentyl)methyl)hydratropateGenerator
Loxoprofen sodium hydrateHMDB
Loxoprofen alcoholHMDB
Sodium 2-(4-(2-oxocyclopentylmethyl)phenyl)propionate dihydrateHMDB
Loxoprofen sodium, (r*,s*)-isomerHMDB
2-(4-((2-Oxocyclopentyl)methyl)phenyl)propionic acidHMDB
2-OCPPPHMDB
Loxoprofen sodium dihydrateHMDB
Sodium loxoprofenHMDB
Chemical FormulaC15H18O3
Average Molecular Weight246.3016
Monoisotopic Molecular Weight246.125594442
IUPAC Name2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
Traditional Nameloxoprofen
CAS Registry Number80382-23-6
SMILES
CC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1
InChI Identifier
InChI=1S/C15H18O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13H,2-4,9H2,1H3,(H,17,18)
InChI KeyYMBXTVYHTMGZDW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 2-phenylpropanoic-acid
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP10(2.99) g/LALOGPS
logP10(3.35) g/LChemAxon
logS10(-3.6) g/LALOGPS
pKa (Strongest Acidic)4.19ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.8 m³·mol⁻¹ChemAxon
Polarizability27.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.14131661259
DarkChem[M-H]-155.23431661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Loxoprofen,1TMS,#1CC(C(=O)O[Si](C)(C)C)C1=CC=C(CC2CCCC2=O)C=C12173.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Loxoprofen,1TMS,#2CC(C(=O)O)C1=CC=C(CC2=C(O[Si](C)(C)C)CCC2)C=C12256.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Loxoprofen,1TMS,#3CC(C(=O)O)C1=CC=C(CC2CCC=C2O[Si](C)(C)C)C=C12220.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Loxoprofen,1TBDMS,#1CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(CC2CCCC2=O)C=C12438.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Loxoprofen,1TBDMS,#2CC(C(=O)O)C1=CC=C(CC2=C(O[Si](C)(C)C(C)(C)C)CCC2)C=C12555.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Loxoprofen,1TBDMS,#3CC(C(=O)O)C1=CC=C(CC2CCC=C2O[Si](C)(C)C(C)(C)C)C=C12494.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Loxoprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gi0-2950000000-f1f143e2589e1aea41732017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loxoprofen GC-MS (1 TMS) - 70eV, Positivesplash10-0600-9882000000-95383cbac1177e9a07262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loxoprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Loxoprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Loxoprofen 35V, Positive-QTOFsplash10-0zfr-0890000000-74ee0167cd6a76ef67d02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Loxoprofen 35V, Negative-QTOFsplash10-001i-0090000000-1b731099acfc2cee4d1a2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 10V, Positive-QTOFsplash10-0002-1290000000-9a370ea3c1893f34ac6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 20V, Positive-QTOFsplash10-0umj-3940000000-2a5656d17e3cdb5b29ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 40V, Positive-QTOFsplash10-0kx0-1900000000-f6a4fd9d3ed427851cb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 10V, Negative-QTOFsplash10-0002-0090000000-c0fa095368edf36565752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 20V, Negative-QTOFsplash10-0udj-2290000000-a000dad805df140f2aeb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 40V, Negative-QTOFsplash10-00ai-9200000000-485777b0ba108a03a92f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 10V, Negative-QTOFsplash10-0f6t-0190000000-319eb623e74a18ded3a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 20V, Negative-QTOFsplash10-0udi-0390000000-0d1645d8c8daa3d6be442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 40V, Negative-QTOFsplash10-014i-2900000000-8d006d601c3437f0eb2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 10V, Positive-QTOFsplash10-01u0-0690000000-117230d5ff547c24425e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 20V, Positive-QTOFsplash10-02bb-2940000000-c41c0ae60ad2bd310b622021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Loxoprofen 40V, Positive-QTOFsplash10-0159-2900000000-457bd9b0f844b6308beb2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB09212
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3828
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLoxoprofen
METLIN IDNot Available
PubChem Compound3965
PDB IDNot Available
ChEBI ID76172
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