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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:39 UTC
Update Date2021-09-14 15:19:36 UTC
HMDB IDHMDB0061142
Secondary Accession Numbers
  • HMDB61142
Metabolite Identification
Common NameFenoprofen glucuronide
DescriptionFenoprofen glucuronide belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond. Fenoprofen glucuronide is a metabolite of fenoprofen. Fenoprofen glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa). Fenoprofen is marketed in the USA as Nalfon. Fenoprofen calcium is used for symptomatic relief for rheumatoid arthritis, osteoarthritis, and mild to moderate pain. Fenoprofen is a non-steroidal anti-inflammatory drug.
Structure
Data?1563866150
SynonymsNot Available
Chemical FormulaC21H22O9
Average Molecular Weight418.394
Monoisotopic Molecular Weight418.126382302
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(3-phenoxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(3-phenoxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C1
InChI Identifier
InChI=1S/C21H22O9/c1-11(12-6-5-9-14(10-12)28-13-7-3-2-4-8-13)20(27)30-21-17(24)15(22)16(23)18(29-21)19(25)26/h2-11,15-18,21-24H,1H3,(H,25,26)/t11?,15-,16-,17+,18-,21-/m0/s1
InChI KeyKXAAUVHIGIFUSM-RVLIQFCMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Diphenylether
  • Diaryl ether
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Acetal
  • Ether
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
Water Solubility1 g/LALOGPS
logP1.31ALOGPS
logP1.71ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.48 m³·mol⁻¹ChemAxon
Polarizability40.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.2831661259
DarkChem[M-H]-197.80731661259
DeepCCS[M+H]+191.08430932474
DeepCCS[M-H]-189.18930932474
DeepCCS[M-2H]-222.43130932474
DeepCCS[M+Na]+196.84630932474
AllCCS[M+H]+199.332859911
AllCCS[M+H-H2O]+196.932859911
AllCCS[M+NH4]+201.532859911
AllCCS[M+Na]+202.232859911
AllCCS[M-H]-192.732859911
AllCCS[M+Na-2H]-193.032859911
AllCCS[M+HCOO]-193.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fenoprofen glucuronideCC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C14458.0Standard polar33892256
Fenoprofen glucuronideCC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C13283.6Standard non polar33892256
Fenoprofen glucuronideCC(C(=O)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C1=CC=CC(OC2=CC=CC=C2)=C13365.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fenoprofen glucuronide,1TMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13187.1Semi standard non polar33892256
Fenoprofen glucuronide,1TMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13188.4Semi standard non polar33892256
Fenoprofen glucuronide,1TMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13192.5Semi standard non polar33892256
Fenoprofen glucuronide,1TMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13188.2Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13196.2Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13192.3Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13195.2Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13196.0Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #5CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13191.7Semi standard non polar33892256
Fenoprofen glucuronide,2TMS,isomer #6CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13191.2Semi standard non polar33892256
Fenoprofen glucuronide,3TMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13222.7Semi standard non polar33892256
Fenoprofen glucuronide,3TMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13230.6Semi standard non polar33892256
Fenoprofen glucuronide,3TMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13222.1Semi standard non polar33892256
Fenoprofen glucuronide,3TMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13218.7Semi standard non polar33892256
Fenoprofen glucuronide,4TMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13265.0Semi standard non polar33892256
Fenoprofen glucuronide,1TBDMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13443.4Semi standard non polar33892256
Fenoprofen glucuronide,1TBDMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13453.8Semi standard non polar33892256
Fenoprofen glucuronide,1TBDMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13452.2Semi standard non polar33892256
Fenoprofen glucuronide,1TBDMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13445.5Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13692.0Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13668.4Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13671.8Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13679.1Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #5CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13665.2Semi standard non polar33892256
Fenoprofen glucuronide,2TBDMS,isomer #6CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13688.2Semi standard non polar33892256
Fenoprofen glucuronide,3TBDMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O)C1=CC=CC(OC2=CC=CC=C2)=C13856.4Semi standard non polar33892256
Fenoprofen glucuronide,3TBDMS,isomer #2CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13880.4Semi standard non polar33892256
Fenoprofen glucuronide,3TBDMS,isomer #3CC(C(=O)O[C@@H]1O[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13842.1Semi standard non polar33892256
Fenoprofen glucuronide,3TBDMS,isomer #4CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C13855.6Semi standard non polar33892256
Fenoprofen glucuronide,4TBDMS,isomer #1CC(C(=O)O[C@@H]1O[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C)C1=CC=CC(OC2=CC=CC=C2)=C14036.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-052b-9411100000-142771712eb35c6fb6c42017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-00rb-9652025000-3bc2c854dbd008b5e1542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fenoprofen glucuronide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Positive-QTOFsplash10-004l-0390400000-13b0912c22b13e64851f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Positive-QTOFsplash10-004i-1590100000-466020693e565d13abd92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Positive-QTOFsplash10-002b-3930000000-4d1b438cd4625c03d0612017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Negative-QTOFsplash10-00r6-1293400000-5c91fc2ec1f6dee9782a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Negative-QTOFsplash10-0006-6893000000-00765df1c5a363205ddb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Negative-QTOFsplash10-0006-9420000000-c306a37bf66053cc9aa12017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Positive-QTOFsplash10-0fba-1791600000-839c4054c99a086694182021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Positive-QTOFsplash10-0002-0920000000-34790b42da973a9af41e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Positive-QTOFsplash10-004j-5900000000-6c9293e8448c4af7afa32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 10V, Negative-QTOFsplash10-014l-1460900000-f1e6424a6b2d61696aae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 20V, Negative-QTOFsplash10-014m-3964300000-4be8b5cc8c7f69527ffc2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fenoprofen glucuronide 40V, Negative-QTOFsplash10-0006-9630000000-932c217ac1f0e1c4fae12021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11742747
PDB IDNot Available
ChEBI IDNot Available
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