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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:07:28 UTC
Update Date2017-10-23 19:15:50 UTC
HMDB IDHMDB0060923
Secondary Accession Numbers
  • HMDB60923
Metabolite Identification
Common NameNaproxen O-glucuronide
DescriptionNaproxen O-glucuronide is a metabolite of naproxen. Naproxen sodium is a nonsteroidal anti-inflammatory drug (NSAID). Naproxen and naproxen sodium are marketed under various trade names, including: Aleve, Anaprox, Antalgin, Feminax Ultra, Flanax, Inza, Midol Extended Relief, Nalgesin, Naposin, Naprelan, Naprogesic, Naprosyn, Narocin, Proxen, Synflex and Xenobid. Naproxen was originally marketed as the prescription drug Naprosyn by Syntex in 1976, and naproxen sodium was first marketed under the trade name Anaprox in 1980. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H22O9
Average Molecular Weight406.3833
Monoisotopic Molecular Weight406.126382302
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C2C=C(C=CC2=C1)[C@H](C)C(=O)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C20H22O9/c1-9(10-3-4-12-8-13(27-2)6-5-11(12)7-10)19(26)29-20-16(23)14(21)15(22)17(28-20)18(24)25/h3-9,14-17,20-23H,1-2H3,(H,24,25)/t9-,14-,15-,16+,17-,20?/m0/s1
InChI KeyXRHIELLXTVJOKM-WDZACEAPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Naphthalene
  • Anisole
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Carboxylic acid ester
  • Secondary alcohol
  • Ether
  • Acetal
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP0.84ALOGPS
logP1.04ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.15 m³·mol⁻¹ChemAxon
Polarizability40.48 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-052r-9713000000-cf3ebdba5fe932e7aff9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-005i-3621119000-6d026138e3771cc5bcfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06sr-0492100000-fd65711e4008d1736cf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08gi-0791000000-769169a96916d3dad3d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08gr-1930000000-99f2960fcd430ce9f89dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vi-1293400000-9ce8a1a3c979690e8e39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-4893000000-6ec9b06cd3e973d924dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vl-9860000000-058f3a2d1cda97ad0cd1View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00160
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available