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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:07:11 UTC
Update Date2021-09-14 15:19:34 UTC
HMDB IDHMDB0060918
Secondary Accession Numbers
  • HMDB60918
Metabolite Identification
Common NameFlurbiprofen glucuronide
DescriptionFlurbiprofen glucuronide is a metabolite of flurbiprofen. Flurbiprofen is a member of the phenylalkanoic acid derivative family of non-steroidal anti-inflammatory drugs (NSAIDs) used to treat the inflammation and pain of arthritis. It is known by the following tradenames: Urbifen marketed by General Pharmaceuticals, Ansaid, marketed by Pfizer, Flurwood by W. Woodward and Froben, by Abbott. Flurbiprofen is also used as an active ingredient in some kinds of throat lozenges. (Wikipedia)
Structure
Data?1563866122
SynonymsNot Available
Chemical FormulaC21H21FO8
Average Molecular Weight420.385
Monoisotopic Molecular Weight420.122045853
IUPAC Name(2R,3R,4R,5S,6R)-6-{[2-(3-fluoro-4-phenylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6R)-6-{[2-(3-fluoro-4-phenylphenyl)propanoyl]oxy}-3,4,5-trihydroxyoxane-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(F)=C(C=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C21H21FO8/c1-10(12-7-8-13(14(22)9-12)11-5-3-2-4-6-11)20(28)30-21-17(25)15(23)16(24)18(29-21)19(26)27/h2-10,15-18,21,23-25H,1H3,(H,26,27)/t10?,15-,16-,17+,18-,21-/m1/s1
InChI KeyPLPQBSOCUVSKTP-QGCNQZRGSA-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
  • Biphenyl
  • Hexose monosaccharide
  • P-cymene
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Beta-hydroxy acid
  • Fluorobenzene
  • Halobenzene
  • Oxane
  • Aryl fluoride
  • Aryl halide
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Polyol
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organofluoride
  • Organohalogen compound
  • Organic oxide
  • 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 Solubility0.24 g/LALOGPS
logP1.27ALOGPS
logP2ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.59 m³·mol⁻¹ChemAxon
Polarizability41.15 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
DeepCCS[M+H]+191.39430932474
DeepCCS[M-H]-189.49830932474
DeepCCS[M-2H]-222.73930932474
DeepCCS[M+Na]+197.00930932474
AllCCS[M+H]+199.532859911
AllCCS[M+H-H2O]+196.932859911
AllCCS[M+NH4]+201.932859911
AllCCS[M+Na]+202.632859911
AllCCS[M-H]-195.132859911
AllCCS[M+Na-2H]-195.532859911
AllCCS[M+HCOO]-196.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Flurbiprofen glucuronideCC(C(=O)O[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C14358.0Standard polar33892256
Flurbiprofen glucuronideCC(C(=O)O[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C13255.8Standard non polar33892256
Flurbiprofen glucuronideCC(C(=O)O[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C(O)=O)C1=CC(F)=C(C=C1)C1=CC=CC=C13257.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13079.4Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13062.1Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13072.3Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13048.3Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13054.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13054.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13063.4Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13030.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13057.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13036.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13058.9Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13082.6Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13070.6Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13056.3Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13113.7Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13317.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13319.6Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13324.1Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13315.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13511.0Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13488.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13498.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13497.2Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13501.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13506.3Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13670.4Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13702.8Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13679.0Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13672.3Semi standard non polar33892256
Flurbiprofen 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=C(C2=CC=CC=C2)C(F)=C13874.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Flurbiprofen glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-054k-9511100000-c363f63720fbd2ca77072017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flurbiprofen glucuronide GC-MS (3 TMS) - 70eV, Positivesplash10-00dj-6982036000-f5f181dcef696893319a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Flurbiprofen 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 - Flurbiprofen glucuronide 10V, Positive-QTOFsplash10-004j-0390400000-0d27141122c9b77293b32017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 20V, Positive-QTOFsplash10-004j-0490100000-b682d83d791ca9121f2d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 40V, Positive-QTOFsplash10-002b-3970000000-52cd7cd01b6c7692f33a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 10V, Negative-QTOFsplash10-00mo-1292500000-b6857366f1cbc160571d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 20V, Negative-QTOFsplash10-002f-5891100000-1ed3968325ea8e11b7ad2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 40V, Negative-QTOFsplash10-0006-9650000000-0290c05d61ccc882eaed2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 10V, Positive-QTOFsplash10-004i-0291400000-7d009e7a9c153fae71552021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 20V, Positive-QTOFsplash10-0002-0960000000-89c768654067f1e3265f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 40V, Positive-QTOFsplash10-002b-2930000000-8a0ebb2d89b5ec4ea41f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 10V, Negative-QTOFsplash10-014l-0850900000-fb91f5da05d7d247c84d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 20V, Negative-QTOFsplash10-004j-0942200000-0075c2669a33a49eae572021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Flurbiprofen glucuronide 40V, Negative-QTOFsplash10-0006-4890000000-24bc70b873727a6f49e02021-10-12Wishart 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 Compound131769992
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