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Record Information
Version3.6
Creation Date2013-06-12 17:32:12 UTC
Update Date2017-09-15 03:16:54 UTC
HMDB IDHMDB0060532
Secondary Accession Numbers
  • HMDB60532
Metabolite Identification
Common NameO-Desmethylvenlafaxine
DescriptionO-Desmethylvenlafaxine is a metabolite of Venlafaxine. Desvenlafaxine (brand name: Pristiq), also known as O-desmethylvenlafaxine, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class developed and marketed by Wyeth (now part of Pfizer). Desvenlafaxine is a synthetic form of the major active metabolite of venlafaxine (sold under the brand names Effexor and Efexor). It is being targeted as the first non-hormonal based treatment for menopause. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
1-[2-(dimethylamino)-1-(4-Hydroxyphenyl)ethyl]cyclohexanolChEBI
4-[2-(dimethylamino)-1-(1-Hydroxycyclohexyl)ethyl]phenolChEBI
O-Desmethylvenlafaxine succinateMeSH
4-(2-(dimethylamino)-1-(1-Hydroxycyclohexyl)ethyl)phenolMeSH
Succinate, desvenlafaxineMeSH
2-(1-Hydroxycyclohexyl)-2-((4-hydroxyphenyl)ethyl)dimethylammonium 3-carboxypropanoate monohydrateMeSH
O DesmethylvenlafaxineMeSH
O Desmethylvenlafaxine succinateMeSH
O-Desmethylvenlafaxine succinate monohydrateMeSH
Succinate, O-desmethylvenlafaxineMeSH
Desvenlafaxine succinateMeSH
Monohydrate, O-desmethylvenlafaxine succinateMeSH
O Desmethylvenlafaxine succinate monohydrateMeSH
O-DesmethylvenlafaxineMeSH
PristiqMeSH
Succinate monohydrate, O-desmethylvenlafaxineMeSH
Chemical FormulaC16H25NO2
Average Molecular Weight263.3752
Monoisotopic Molecular Weight263.188529049
IUPAC Name4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol
Traditional Namedesvenlafaxine
CAS Registry NumberNot Available
SMILES
CN(C)CC(C1=CC=C(O)C=C1)C1(O)CCCCC1
InChI Identifier
InChI=1S/C16H25NO2/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16/h6-9,15,18-19H,3-5,10-12H2,1-2H3
InChI KeyKYYIDSXMWOZKMP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentCyclohexanols
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Cyclohexanol
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • 1,3-aminoalcohol
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility1.4 mg/mLALOGPS
logP2.6ALOGPS
logP2.29ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.54 m3·mol-1ChemAxon
Polarizability30.29 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0090000000-90abc876cc91a398d25dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03y0-0960000000-0219d7d7ea1a46c8cfdfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-529d7fb237a99866f0b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-ccb6c8906a1ac7d27cd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0290000000-422a5daa0d4bf51308efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0910000000-03ecfc411d730c35b892View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-0900000000-d0fa1892dfaae0510ee8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001m-0900000000-7515704132219cf15c78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0090000000-1a8bdddd358a8706e896View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-c218ef4ab652831ee930View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-4090000000-b1767a9c9c01cb43bca9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9320000000-e38b2ae07ab3cc9b7693View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9600000000-edbb26312a47b22bffb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9800000000-b41801091e3c7132fec9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9800000000-4b30d7e9d71dab81d9d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0090000000-5e859f484b6e3a5560c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-06r2-4090000000-ef1215dc6fc4eb904b90View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9310000000-dac7bd983af34469bc5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-9600000000-8ea073e198c8a9a9a528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00054
      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 LinkHMDB0060532
      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