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Record Information
Version3.6
Creation Date2013-07-22 19:52:20 UTC
Update Date2017-08-18 12:59:52 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 FormulaC22H24F3NO8
Average Molecular Weight487.4231
Monoisotopic Molecular Weight487.145401364
IUPAC Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-[({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amino)oxy]oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-3,4,5-trihydroxy-6-[({3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl}amino)oxy]oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@@H](O)C(ONCCC(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/C22H24F3NO8/c23-22(24,25)13-6-8-14(9-7-13)32-15(12-4-2-1-3-5-12)10-11-26-34-21-18(29)16(27)17(28)19(33-21)20(30)31/h1-9,15-19,21,26-29H,10-11H2,(H,30,31)/t15?,16-,17-,18+,19-,21?/m0/s1
InChI KeyLUIHTMWIRNJSNW-FRYOACGXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as glucuronic acid derivatives. These are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Trifluoromethylbenzene
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Benzenoid
  • Pyran
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • N-organohydroxylamine
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alkyl fluoride
  • Organic nitrogen compound
  • Alcohol
  • Alkyl halide
  • Organopnictogen compound
  • Organohalogen compound
  • Organofluoride
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 mg/mLALOGPS
logP1.71ALOGPS
logP0.45ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)4.68ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area137.71 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity119.86 m3·mol-1ChemAxon
Polarizability44.64 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
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 IDDBMET00964
      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
      NuGOwiki LinkHMDB0061170
      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