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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:40 UTC
Update Date2018-05-20 20:32:35 UTC
HMDB IDHMDB0060997
Secondary Accession Numbers
  • HMDB60997
Metabolite Identification
Common NameO-Desmethyltramadol
DescriptionO-Desmethyltramadol is a metabolite of tramadol. O-Desmethyltramadol (O-DSMT) 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
DesmetramadolHMDB
O-DSMTHMDB
O-DemethyltramadolHMDB
(+)-O-DemethyltramadolHMDB
(+)-O-DesmethyltramadolHMDB
M1HMDB
Tramadol m1 metaboliteMeSH
O-Demethyl tramadolMeSH
O-Demethyltramadol hydrochlorideMeSH
Chemical FormulaC15H23NO2
Average Molecular Weight249.354
Monoisotopic Molecular Weight249.172878985
IUPAC Name3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
Traditional Name3-[(1R,2R)-2-[(dimethylamino)methyl]-1-hydroxycyclohexyl]phenol
CAS Registry Number144830-14-8
SMILES
CN(C)C[C@H]1CCCC[C@]1(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/t13-,15+/m1/s1
InChI KeyUWJUQVWARXYRCG-HIFRSBDPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassCyclohexylphenols
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
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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-1.8ALOGPS
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
Polarizability28.5 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0190000000-2e56a5a569b4ba1aeb14View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kar-2490000000-450fde7726d06cd79e38View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9210000000-4c90c254991bcc168550View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-a4efe14581c4cad5a518View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-4490000000-cc94eae2e10fb69891aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-1e924d7a8f6fc069a3abView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
      Phenol Explorer Compound IDNot Available
      FoodDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider ID8014523
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkDesmetramadol
      METLIN IDNot Available
      PubChem Compound9838803
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available