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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:52:27 UTC
Update Date2017-10-23 19:15:54 UTC
HMDB IDHMDB0061172
Secondary Accession Numbers
  • HMDB61172
Metabolite Identification
Common NameO-Desmethylvenlafaxine glucuronide
DescriptionO-Desmethylvenlafaxine glucuronide is a metabolite of venlafaxine. Venlafaxine is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class. First introduced by Wyeth in 1993, now marketed by Pfizer, it is licensed for the treatment of major depressive disorder (MDD), as a treatment for generalized anxiety disorder, and comorbid indications in certain anxiety disorders with depression. In 2007, venlafaxine was the sixth most commonly prescribed antidepressant on the U.S. retail market, with 17.2 million prescriptions. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC20H29NO8
Average Molecular Weight411.4462
Monoisotopic Molecular Weight411.189316909
IUPAC Name(2S,3S,4S,5R,6S)-6-{4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-{4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
NCC(C1=CC=C(O[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)C(O)=O)C=C1)C1(O)CCCCC1
InChI Identifier
InChI=1S/C20H29NO8/c21-10-13(20(27)8-2-1-3-9-20)11-4-6-12(7-5-11)28-19-16(24)14(22)15(23)17(29-19)18(25)26/h4-7,13-17,19,22-24,27H,1-3,8-10,21H2,(H,25,26)/t13?,14-,15-,16+,17-,19+/m0/s1
InChI KeyVNRFTNKWISCOMJ-KUIQUDTGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Fatty acyl glycoside
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Cyclohexanol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Tertiary alcohol
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Carboxylic acid
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Primary amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

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 Solubility2.11 g/LALOGPS
logP-2.3ALOGPS
logP-2.4ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area162.7 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.48 m³·mol⁻¹ChemAxon
Polarizability41.77 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, Positivesplash10-001l-9125000000-83d98ea4095fa4e96364View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-08mi-8815249000-25d9ebfb838b2f88443bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00mx-0079100000-712de3682edb577c22f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0091000000-c1060dd5fb17618b44cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-8190000000-237e841e2de83a126bdbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-1289700000-427d4e4b996d57ddc367View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1294000000-376169272f713ef80b11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-4590000000-a71b8ea1885d77a1906aView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Venlafaxine Metabolism PathwayPw000612Pw000612 greyscalePw000612 simpleNot Available
Displaying 1 entry
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 IDDBMET00967
      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