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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-10-23 19:06:21 UTC
HMDB IDHMDB0014713
Secondary Accession Numbers
  • HMDB14713
Metabolite Identification
Common NameFenoprofen
DescriptionFenoprofen is only found in individuals that have used or taken this drug. It is an anti-inflammatory analgesic and antipyretic highly bound to plasma proteins. It is pharmacologically similar to aspirin, but causes less gastrointestinal bleeding. [PubChem]Fenoprofen's exact mode of action is unknown, but it is thought that prostaglandin synthetase inhibition is involved. Fenoprofen has been shown to inhibit prostaglandin synthetase isolated from bovine seminal vesicles.
Structure
Thumb
Synonyms
ValueSource
(+-)-2-(3-Phenoxyphenyl)propionic acidChEBI
(+-)-m-Phenoxyhydratropic acidChEBI
2-(3-Phenoxyphenyl)propionic acidChEBI
2-(m-Phenoxyphenyl)propionic acidChEBI
alpha-(m-Phenoxyphenyl)propionic acidChEBI
alpha-Methyl-3-phenoxybenzeneacetic acidChEBI
FenoprofeneChEBI
FenoprofenoChEBI
FenoprofenumChEBI
(+-)-2-(3-Phenoxyphenyl)propionateGenerator
(+-)-m-PhenoxyhydratropateGenerator
2-(3-Phenoxyphenyl)propionateGenerator
2-(m-Phenoxyphenyl)propionateGenerator
a-(m-Phenoxyphenyl)propionateGenerator
a-(m-Phenoxyphenyl)propionic acidGenerator
alpha-(m-Phenoxyphenyl)propionateGenerator
α-(m-phenoxyphenyl)propionateGenerator
α-(m-phenoxyphenyl)propionic acidGenerator
a-Methyl-3-phenoxybenzeneacetateGenerator
a-Methyl-3-phenoxybenzeneacetic acidGenerator
alpha-Methyl-3-phenoxybenzeneacetateGenerator
α-methyl-3-phenoxybenzeneacetateGenerator
α-methyl-3-phenoxybenzeneacetic acidGenerator
Feneprofen calcium salt dihydrateHMDB
Fenoprofen calciumHMDB
Fenoprofen calcium hydrateHMDB
Calcium, fenoprofenMeSH
Fenoprofen dihydrate, calcium saltMeSH
NalfonMeSH
NalgesicMeSH
Fenoprofen, anhydrous, calcium saltMeSH
Chemical FormulaC15H14O3
Average Molecular Weight242.2699
Monoisotopic Molecular Weight242.094294314
IUPAC Name2-(3-phenoxyphenyl)propanoic acid
Traditional Namefenoprofen
CAS Registry Number34597-40-5
SMILES
CC(C(O)=O)C1=CC(OC2=CC=CC=C2)=CC=C1
InChI Identifier
InChI=1S/C15H14O3/c1-11(15(16)17)12-6-5-9-14(10-12)18-13-7-3-2-4-8-13/h2-11H,1H3,(H,16,17)
InChI KeyRDJGLLICXDHJDY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • 2-phenylpropanoic-acid
  • Diaryl ether
  • Phenoxy compound
  • Phenol ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.081 g/LNot Available
LogP3.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.081 g/LALOGPS
logP3.87ALOGPS
logP3.65ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
pKa (Strongest Basic)-8.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.18 m³·mol⁻¹ChemAxon
Polarizability25.3 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-4920000000-d5b009ac51d1a009654fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9430000000-d3139bfe3d51e590f420View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0900000000-856a8aff822346800d28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0900000000-856a8aff822346800d28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0002-0900000000-856a8aff822346800d28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0002-0900000000-0b8ab61fb369335a1792View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-0a6fe356f953cf25a938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0390000000-a7dcddcdf276077845ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1950000000-e911262fea4253a2bc1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-5900000000-5a1de84e2ebbf6ebb083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0390000000-10cd32d4365175fef19fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-2950000000-899958861c820483a049View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-5dd892f971b30ad34901View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Fenoprofen Action PathwayPw000673Pw000673 greyscalePw000673 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00573 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00573 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00573
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3225
KEGG Compound IDC06997
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFenoprofen
METLIN IDNot Available
PubChem Compound3342
PDB IDNot Available
ChEBI ID5004
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. [PubMed:17050798 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Poggi JC, Barissa GR, Donadi EA, Foss MC, Cunha FQ, Lanchote VL, dos Reis ML: Pharmacodynamics, chiral pharmacokinetics, and pharmacokinetic-pharmacodynamic modeling of fenoprofen in patients with diabetes mellitus. J Clin Pharmacol. 2006 Nov;46(11):1328-36. [PubMed:17050798 ]