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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:11:40 UTC
Update Date2021-09-14 15:45:53 UTC
HMDB IDHMDB0060997
Secondary Accession Numbers
  • HMDB60997
Metabolite Identification
Common NameO-Desmethyltramadol
DescriptionO-Desmethyltramadol, also known as M1 or O-DSMT, belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. O-Desmethyltramadol is a very strong basic compound (based on its pKa). Within humans, O-desmethyltramadol participates in a number of enzymatic reactions. In particular, O-desmethyltramadol and formaldehyde can be biosynthesized from tramadol through the action of the enzyme cytochrome P450 2D6. In addition, O-desmethyltramadol and uridine diphosphate glucuronic acid can be converted into O-desmethyltramadol glucuronide and uridine 5'-diphosphate; which is mediated by the enzymes UDP-glucuronosyltransferase 2B7 and UDP-glucuronosyltransferase 1-8. O-Desmethyltramadol is the most important metabolite of tramadol produced in the liver after tramadol is consumed. In humans, O-desmethyltramadol is involved in tramadol metabolism pathway. This metabolite is considerably more potent as a μ-opioid agonist than the parent compound (Wikipedia ). O-Desmethyltramadol (O-DSMT) is an opioid analgesic and the main active metabolite of tramadol. O-Desmethyltramadol is a metabolite of tramadol.
Structure
Data?1563866132
Synonyms
ValueSource
DesmetramadolHMDB
O-DSMTHMDB
O-DemethyltramadolHMDB
(+)-O-DemethyltramadolHMDB
(+)-O-DesmethyltramadolHMDB
M1HMDB
Tramadol m1 metaboliteHMDB
O-Demethyl tramadolHMDB
O-Demethyltramadol hydrochlorideHMDB
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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+160.83830932474
DeepCCS[M-H]-158.4830932474
DeepCCS[M-2H]-191.36630932474
DeepCCS[M+Na]+166.93130932474
AllCCS[M+H]+159.032859911
AllCCS[M+H-H2O]+155.332859911
AllCCS[M+NH4]+162.532859911
AllCCS[M+Na]+163.532859911
AllCCS[M-H]-164.532859911
AllCCS[M+Na-2H]-164.832859911
AllCCS[M+HCOO]-165.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
O-DesmethyltramadolCN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12827.9Standard polar33892256
O-DesmethyltramadolCN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12064.0Standard non polar33892256
O-DesmethyltramadolCN(C)C[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12076.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
O-Desmethyltramadol,1TMS,isomer #1CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C11986.7Semi standard non polar33892256
O-Desmethyltramadol,1TMS,isomer #2CN(C)C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C12016.2Semi standard non polar33892256
O-Desmethyltramadol,2TMS,isomer #1CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C12026.2Semi standard non polar33892256
O-Desmethyltramadol,1TBDMS,isomer #1CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C12242.8Semi standard non polar33892256
O-Desmethyltramadol,1TBDMS,isomer #2CN(C)C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12273.0Semi standard non polar33892256
O-Desmethyltramadol,2TBDMS,isomer #1CN(C)C[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12492.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Desmethyltramadol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOFsplash10-0002-0090000000-136b75d654ddf273b0402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOFsplash10-0002-0090000000-cf3096627c4781f271e52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 30V, Negative-QTOFsplash10-0002-0090000000-1407f9618c4c09bd238e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 30V, Positive-QTOFsplash10-000t-0910000000-ede5dd9d4181f099f0eb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOFsplash10-0udi-0090000000-1a79634c0982a7a17c0e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOFsplash10-0udi-0090000000-7e2038f71f53553e811a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 30V, Positive-QTOFsplash10-000t-0910000000-e61d1a45f61e0989fe1c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOFsplash10-000t-0900000000-268897d22fcc39fe16a02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - O-Desmethyltramadol 50V, Positive-QTOFsplash10-000t-0900000000-b0ebe3a83bce1e12ca3c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOFsplash10-0f89-0190000000-2e56a5a569b4ba1aeb142016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOFsplash10-0kar-2490000000-450fde7726d06cd79e382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOFsplash10-0pbc-9210000000-4c90c254991bcc1685502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOFsplash10-0002-0090000000-a4efe14581c4cad5a5182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOFsplash10-0002-4490000000-cc94eae2e10fb69891aa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Negative-QTOFsplash10-0006-9220000000-1e924d7a8f6fc069a3ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Negative-QTOFsplash10-0002-0090000000-67c119790b4a702e18122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Negative-QTOFsplash10-0002-1690000000-2523c31ef432eaac871d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Negative-QTOFsplash10-00di-2900000000-58454bbc33d3695f62db2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 10V, Positive-QTOFsplash10-0zfr-1090000000-618c15540807c1882add2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 20V, Positive-QTOFsplash10-0a4r-9520000000-ff25b62d622eab2ca2412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Desmethyltramadol 40V, Positive-QTOFsplash10-052r-5900000000-2cb275df93a1b256dc2f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available