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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:25:18 UTC
Update Date2021-09-26 22:59:32 UTC
HMDB IDHMDB0248956
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenoxaprofen
DescriptionBenoxaprofen, also known as lilly 90459 or oraflex, 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. Based on a literature review a significant number of articles have been published on Benoxaprofen. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benoxaprofen is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benoxaprofen is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
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 Weight301.724
Monoisotopic Molecular Weight301.050570962
IUPAC Name2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid
Traditional Namebenoxaprofen
CAS Registry NumberNot Available
SMILES
CC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
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
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]+172.34530932474
DeepCCS[M-H]-169.98730932474
DeepCCS[M-2H]-203.74530932474
DeepCCS[M+Na]+178.97230932474
AllCCS[M+H]+166.932859911
AllCCS[M+H-H2O]+163.532859911
AllCCS[M+NH4]+170.032859911
AllCCS[M+Na]+170.932859911
AllCCS[M-H]-168.132859911
AllCCS[M+Na-2H]-167.332859911
AllCCS[M+HCOO]-166.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenoxaprofenCC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C13796.9Standard polar33892256
BenoxaprofenCC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C12582.2Standard non polar33892256
BenoxaprofenCC(C(O)=O)C1=CC2=C(OC(=N2)C2=CC=C(Cl)C=C2)C=C12631.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benoxaprofen EI-B (Non-derivatized)splash10-0a4i-7294000000-6fce0cace9618294c8792017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benoxaprofen GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n0-0950000000-5d0b37b42442ccd580a82017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benoxaprofen GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benoxaprofen GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benoxaprofen GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 10V, Positive-QTOFsplash10-0udi-0079000000-378fba1ed509d2be0ded2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 20V, Positive-QTOFsplash10-0pc0-0092000000-22ee08cb4cbf3cd04f7e2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 40V, Positive-QTOFsplash10-0j5a-4980000000-a80cc3aa977c018a22e72017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 10V, Negative-QTOFsplash10-0udi-0049000000-ff347f83a8f58bf601822017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 20V, Negative-QTOFsplash10-0pb9-0194000000-c35a3ca878f97546a6732017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 40V, Negative-QTOFsplash10-03fr-3970000000-812dcf8d86d5f3ea9da22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 10V, Negative-QTOFsplash10-0a4i-0091000000-c67b46a01c9b911260262021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 20V, Negative-QTOFsplash10-0a4i-0090000000-6a6e0a7917aff75d58972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 40V, Negative-QTOFsplash10-001i-8790000000-a4436e7d143bb705a47d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 10V, Positive-QTOFsplash10-0pb9-0097000000-381c8e8159e9ef91df4d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 20V, Positive-QTOFsplash10-0a4i-0091000000-a21e3f21df01b9e4e43c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benoxaprofen 40V, Positive-QTOFsplash10-053i-0890000000-b73f7497e3790f3c5fca2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04812
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID36518
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenoxaprofen
METLIN IDNot Available
PubChem Compound39941
PDB IDNot Available
ChEBI ID76114
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 References
  1. 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. [PubMed:31557052 ]