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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:40 UTC
Update Date2017-12-07 18:37:51 UTC
HMDB IDHMDB0060997
Secondary Accession Numbers
  • HMDB60997
Metabolite Identification
Common NameO-Desmethyltramadol
DescriptionO-Desmethyltramadol is a metabolite of tramadol. O-Desmethyltramadol (O-DT) is an opioid analgesic and the main active metabolite of tramadol. (+)-O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. This metabolite is considerably more potent as a μ opioid agonist than the parent compound. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
O-Demethyl tramadolMeSH
O-Demethyltramadol hydrochlorideMeSH
O-DemethyltramadolMeSH
Tramadol m1 metaboliteMeSH
Chemical FormulaC15H23NO2
Average Molecular Weight249.3486
Monoisotopic Molecular Weight249.172878985
IUPAC Name3-{2-[(dimethylamino)methyl]-1-hydroxycyclohexyl}phenol
Traditional NameO-desmethyltramadol
CAS Registry NumberNot Available
SMILES
CN(C)CC1CCCCC1(O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C15H23NO2/c1-16(2)11-13-6-3-4-9-15(13,18)12-7-5-8-14(17)10-12/h5,7-8,10,13,17-18H,3-4,6,9,11H2,1-2H3
InChI KeyUWJUQVWARXYRCG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cyclohexylphenols. These are compounds containing a cyclohexane lined to a phenol group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentCyclohexylphenols
Alternative Parents
Substituents
  • Cyclohexylphenol
  • Cyclohexanol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Cyclic alcohol
  • Tertiary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amine
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility3.53 g/LALOGPS
logP2.26ALOGPS
logP1.72ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.62ChemAxon
pKa (Strongest Basic)8.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area43.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity73.79 m³·mol⁻¹ChemAxon
Polarizability28.53 ųChemAxon
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-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9450000000-ddc312060c61cf8d77c2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5019000000-103fa6c85cb52e3c975dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0090000000-1d83b239d0bb5e23dcf3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pc9-3490000000-92e4f896ac68d558a95bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9110000000-640af0795a48941dfabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-83931f5e8c548f585fd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0032-3590000000-c8ab32a824ab6be8fc5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9320000000-e1bbba86e0914c222c0cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Tramadol Metabolism PathwayPw000613Pw000613 greyscalePw000613 simpleNot 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 IDDBMET00324
      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 LinkO-Desmethyltramadol
      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