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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:26 UTC
Update Date2021-09-14 15:45:15 UTC
HMDB IDHMDB0060851
Secondary Accession Numbers
  • HMDB60851
Metabolite Identification
Common NameN,O-Didesmethyltramadol
DescriptionN,O-Didesmethyltramadol, also known as M5, belongs to the class of organic compounds known as cyclohexylphenols. Cyclohexylphenols are compounds containing a cyclohexane lined to a phenol group. N,O-Didesmethyltramadol is a very strong basic compound (based on its pKa). Within humans, N,O-didesmethyltramadol participates in a number of enzymatic reactions. In particular, N,O-didesmethyltramadol and formaldehyde can be biosynthesized from N-desmethyltramadol; which is catalyzed by the enzyme cytochrome P450 2D6. In addition, N,O-didesmethyltramadol and formaldehyde can be biosynthesized from O-desmethyltramadol through its interaction with the enzyme cytochrome P450 2D6. N,O-Didesmethyltramadol is a metabolite of tramadol. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. In humans, N,O-didesmethyltramadol is involved in tramadol metabolism pathway. Tramadol hydrochloride (trademarked as Conzip, Ryzolt, Ultracet, Ultram in the USA; Ralivia and Zytram XL in Canada) is a centrally-acting synthetic analgesic used to treat moderate to moderately-severe pain. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia).
Structure
Data?1563866113
Synonyms
ValueSource
O,N-DidemethyltramadolHMDB
O,N-DidesmethyltramadolHMDB
M5HMDB
Chemical FormulaC14H21NO2
Average Molecular Weight235.322
Monoisotopic Molecular Weight235.157228921
IUPAC Name3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol
Traditional Name3-[(1R,2R)-1-hydroxy-2-[(methylamino)methyl]cyclohexyl]phenol
CAS Registry Number144830-18-2
SMILES
CNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C14H21NO2/c1-15-10-12-5-2-3-8-14(12,17)11-6-4-7-13(16)9-11/h4,6-7,9,12,15-17H,2-3,5,8,10H2,1H3/t12-,14+/m1/s1
InChI KeyCJXNQQLTDXASSR-OCCSQVGLSA-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
  • Phenol
  • Aralkylamine
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • 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 Solubility0.88 g/LALOGPS
logP1.71ALOGPS
logP1.03ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.22ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area52.49 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity68.49 m³·mol⁻¹ChemAxon
Polarizability26.73 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
DarkChem[M+H]+157.96731661259
DarkChem[M-H]-156.95831661259
DeepCCS[M+H]+157.8830932474
DeepCCS[M-H]-155.52230932474
DeepCCS[M-2H]-188.47330932474
DeepCCS[M+Na]+163.97430932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.732859911
AllCCS[M+NH4]+159.232859911
AllCCS[M+Na]+160.232859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-160.332859911
AllCCS[M+HCOO]-160.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,O-DidesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12761.6Standard polar33892256
N,O-DidesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12120.0Standard non polar33892256
N,O-DidesmethyltramadolCNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12103.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N,O-Didesmethyltramadol,1TMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C12061.8Semi standard non polar33892256
N,O-Didesmethyltramadol,1TMS,isomer #2CNC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C12076.9Semi standard non polar33892256
N,O-Didesmethyltramadol,1TMS,isomer #3CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C2217.7Semi standard non polar33892256
N,O-Didesmethyltramadol,2TMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C12092.9Semi standard non polar33892256
N,O-Didesmethyltramadol,2TMS,isomer #2CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C2176.0Semi standard non polar33892256
N,O-Didesmethyltramadol,2TMS,isomer #3CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C2179.6Semi standard non polar33892256
N,O-Didesmethyltramadol,3TMS,isomer #1CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C2176.8Semi standard non polar33892256
N,O-Didesmethyltramadol,3TMS,isomer #1CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C2263.3Standard non polar33892256
N,O-Didesmethyltramadol,3TMS,isomer #1CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C2307.0Standard polar33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C12300.4Semi standard non polar33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #2CNC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12326.6Semi standard non polar33892256
N,O-Didesmethyltramadol,1TBDMS,isomer #3CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C2471.0Semi standard non polar33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #1CNC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12520.5Semi standard non polar33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #2CN(C[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C2659.5Semi standard non polar33892256
N,O-Didesmethyltramadol,2TBDMS,isomer #3CN(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C2676.7Semi standard non polar33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1CN(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)=C1)[Si](C)(C)C(C)(C)C2864.9Semi standard non polar33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1CN(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)=C1)[Si](C)(C)C(C)(C)C2921.8Standard non polar33892256
N,O-Didesmethyltramadol,3TBDMS,isomer #1CN(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)=C1)[Si](C)(C)C(C)(C)C2617.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethyltramadol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9730000000-1723c89493b2caae724f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethyltramadol GC-MS (2 TMS) - 70eV, Positivesplash10-01ox-6049000000-b5b87e37310bf5e1de812017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,O-Didesmethyltramadol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 10V, Positive-QTOFsplash10-00kr-0190000000-619eeceb75338ebbdc032017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 20V, Positive-QTOFsplash10-052r-4790000000-d5323d821498effc82f62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 40V, Positive-QTOFsplash10-0pvl-9200000000-c5c1ec5f1e2c1d14561a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 10V, Negative-QTOFsplash10-001i-0090000000-e1a59bf22492c88440812017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 20V, Negative-QTOFsplash10-001l-4790000000-98a9934098edb08993342017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,O-Didesmethyltramadol 40V, Negative-QTOFsplash10-0006-9510000000-6d17e0f6fee1b54396b72017-10-06Wishart 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 ID7991856
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9816106
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