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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:52:20 UTC
Update Date2018-05-20 20:34:50 UTC
HMDB IDHMDB0061170
Secondary Accession Numbers
  • HMDB61170
Metabolite Identification
Common NameNorfluoxetine glucuronide
DescriptionNorfluoxetine glucuronide is a metabolite of fluoxetine. Fluoxetine (also known by the tradenames Prozac, Sarafem, Fontex, among others) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. Fluoxetine was first documented in 1974 by scientists from Eli Lilly and Company. It was presented to the U.S. Food and Drug Administration in February 1977, with Eli Lilly receiving final approval to market the drug in December 1987. Fluoxetine went off-patent in August 2001 (Wikipedia).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H24F3NO7
Average Molecular Weight471.429
Monoisotopic Molecular Weight471.150486606
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amino)oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amino)oxane-2-carboxylic acid
CAS Registry Number96735-72-7
SMILES
O[C@@H]1[C@@H](O)[C@H](NCCC(OC2=CC=C(C=C2)C(F)(F)F)C2=CC=CC=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C22H24F3NO7/c23-22(24,25)13-6-8-14(9-7-13)32-15(12-4-2-1-3-5-12)10-11-26-20-18(29)16(27)17(28)19(33-20)21(30)31/h1-9,15-20,26-29H,10-11H2,(H,30,31)/t15?,16-,17-,18+,19-,20+/m0/s1
InChI KeyGXZQMXPRYAFVRG-OJRVOLPLSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through a N-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-glucuronides
Alternative Parents
Substituents
  • N-glucuronide
  • 1-n-glucuronide
  • Glycosyl compound
  • N-glycosyl compound
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Monosaccharide
  • Pyran
  • Oxane
  • Hemiaminal
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Polyol
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organohalogen compound
  • Organofluoride
  • Carbonyl group
  • Organic oxide
  • Alkyl halide
  • Alcohol
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility0.17 g/LALOGPS
logP1.59ALOGPS
logP-0.39ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)7.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area128.48 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity107.9 m³·mol⁻¹ChemAxon
Polarizability43.32 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID57530480
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound71751199
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available