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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:52:09 UTC
Update Date2017-10-23 19:15:53 UTC
HMDB IDHMDB0061167
Secondary Accession Numbers
  • HMDB61167
Metabolite Identification
Common NameN,O-Didesmethylvenlafaxine glucuronide
DescriptionN,O-Didesmethylvenlafaxine 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 FormulaC21H31NO8
Average Molecular Weight425.4727
Monoisotopic Molecular Weight425.204966973
IUPAC Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{4-[1-(1-hydroxycyclohexyl)-2-(methylamino)ethyl]phenoxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CNCC(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/C21H31NO8/c1-22-11-14(21(28)9-3-2-4-10-21)12-5-7-13(8-6-12)29-20-17(25)15(23)16(24)18(30-20)19(26)27/h5-8,14-18,20,22-25,28H,2-4,9-11H2,1H3,(H,26,27)/t14?,15-,16-,17+,18-,20+/m0/s1
InChI KeyUDNAJOOLWIWCAW-SQBZNDFJSA-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
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Alkyl glycoside
  • O-glycosyl compound
  • Phenoxy compound
  • Phenol ether
  • Beta-hydroxy acid
  • Aralkylamine
  • Cyclohexanol
  • Hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Oxane
  • Benzenoid
  • Pyran
  • Cyclic alcohol
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic nitrogen compound
  • 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 Solubility2.81 g/LALOGPS
logP0.11ALOGPS
logP-2.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area148.71 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.26 m³·mol⁻¹ChemAxon
Polarizability43.83 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, Positivesplash10-0006-9003100000-0d06e3e0ccb1ccd20729View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-9020022000-3dcb6e99e4b209c2c3a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pe9-0095600000-7b950922b39b94f728abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0090000000-d4f7d86a904dbfbcb2ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-7190000000-1d69365a9af26527072bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ea-3264900000-55a40ac8e5bde5ffa6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-1293100000-5079cf6ecbdb43045d19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-5490000000-1baa6832c26bd141b2f4View 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 IDDBMET00958
      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