benzoxaprofen (CHEM042909)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 10:25:02 UTC
Update Date2016-11-09 01:22:49 UTC
Accession NumberCHEM042909
Identification
Common Namebenzoxaprofen
ClassSmall Molecule
DescriptionA monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects including liver necrosis, photosensitivity, and carcinogenicity in animals.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-BenoxaprofenChEBI
(1)-2-(4-Chlorophenyl)benzoxazole-5-propionic acidChEBI
2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acidChEBI
2-(p-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acidChEBI
BenoxaprofeneChEBI
BenoxaprofenoChEBI
BenoxaprofenumChEBI
DL-BenoxaprofenChEBI
Lilly 90459ChEBI
OraflexKegg
(1)-2-(4-Chlorophenyl)benzoxazole-5-propionateGenerator
2-(4-Chlorophenyl)-a-methyl-5-benzoxazoleacetateGenerator
2-(4-Chlorophenyl)-a-methyl-5-benzoxazoleacetic acidGenerator
2-(4-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetateGenerator
2-(4-Chlorophenyl)-α-methyl-5-benzoxazoleacetateGenerator
2-(4-Chlorophenyl)-α-methyl-5-benzoxazoleacetic acidGenerator
2-(p-Chlorophenyl)-a-methyl-5-benzoxazoleacetateGenerator
2-(p-Chlorophenyl)-a-methyl-5-benzoxazoleacetic acidGenerator
2-(p-Chlorophenyl)-alpha-methyl-5-benzoxazoleacetateGenerator
2-(p-Chlorophenyl)-α-methyl-5-benzoxazoleacetateGenerator
2-(p-Chlorophenyl)-α-methyl-5-benzoxazoleacetic acidGenerator
Benoxaprofen, (+)-isomerHMDB
LRCL 3794HMDB
Benoxaprofen, (+-)-isomerHMDB
Benoxaprofen, monosodium saltHMDB
Benoxaprofen, ammonium saltHMDB
Benoxaprofen, (-)-isomerHMDB
2-[2-(4-Chlorophenyl)-1,3-benzoxazol-5-yl]propanoateHMDB
Chemical FormulaC16H12ClNO3
Average Molecular Mass301.724 g/mol
Monoisotopic Mass301.051 g/mol
CAS Registry Number51234-28-7
IUPAC Name2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
Traditional Namebenoxaprofen
SMILESCC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C1
InChI IdentifierInChI=1S/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)
InChI KeyMITFXPHMIHQXPI-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenyl-1,3-oxazoles. These are aromatic heterocyclic compounds containing a 1,3-oxazole substituted at one or more positions by a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassOxazoles
Direct ParentPhenyl-1,3-oxazoles
Alternative Parents
Substituents
  • Phenyl-1,3-oxazole
  • Benzoxazole
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.032 g/LALOGPS
logP4.22ALOGPS
logP4.13ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)0.091ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.51 m³·mol⁻¹ChemAxon
Polarizability31.34 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7294000000-6fce0cace9618294c879Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-0950000000-5d0b37b42442ccd580a8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0079000000-378fba1ed509d2be0dedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc0-0092000000-22ee08cb4cbf3cd04f7eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0j5a-4980000000-a80cc3aa977c018a22e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0049000000-ff347f83a8f58bf60182Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-0194000000-c35a3ca878f97546a673Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03fr-3970000000-812dcf8d86d5f3ea9da2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0091000000-c67b46a01c9b91126026Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0090000000-6a6e0a7917aff75d5897Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-8790000000-a4436e7d143bb705a47dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-0097000000-381c8e8159e9ef91df4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0091000000-a21e3f21df01b9e4e43cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053i-0890000000-b73f7497e3790f3c5fcaSpectrum
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
DrugBank IDDB04812
HMDB IDHMDB0248956
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBenoxaprofen
Chemspider ID36518
ChEBI ID76114
PubChem Compound ID39941
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19439485
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19773537
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21128314
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22514582
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23250699
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2413686
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=2833969
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2947294
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3981515
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=6407402
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6526401
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6645654
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6813936
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6993669
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6993670
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6993671
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6993672
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=7044799
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=7044801
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=7084283
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=7084287
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=7221526
23. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26.