Loxoprofen (CHEM018172)

Record Information
Version1.0
Creation Date2016-05-22 05:02:37 UTC
Update Date2026-08-19 11:04:05 UTC
Accession NumberCHEM018172
Identification
Common NameLoxoprofen
ClassSmall Molecule
Description
A monocarboxylic acid that is propionic acid in which one of the hydrogens at position 2 is substituted by a 4-[(2-oxocyclopentyl)methyl]phenyl group. A prodrug that is rapidly converted into its active trans-alcohol metabolite following oral administration.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass246.302 g/mol
Monoisotopic Mass246.126 g/mol
CAS Registry Number68767-14-6
IUPAC Name2-{4-[(2-oxocyclopentyl)methyl]phenyl}propanoic acid
Traditional Nameloxoprofen
SMILESCC(C(O)=O)C1=CC=C(CC2CCCC2=O)C=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP2.99ALOGPS
logP3.35ChemAxon
logS-3.6ALOGPS
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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB09212
HMDB IDHMDB0041920
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLoxoprofen
Chemspider ID3828
ChEBI ID76172
PubChem Compound ID3965
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References