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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-04 19:03:23 UTC
Update Date2021-09-14 15:44:49 UTC
HMDB IDHMDB0060850
Secondary Accession Numbers
  • HMDB60850
Metabolite Identification
Common NameN,N,O-Tridesmethyltramadol
DescriptionN,N,O-Tridesmethyltramadol is a metabolite of tramadol. 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. The drug has a wide range of applications, including treatment of rheumatoid arthritis, restless legs syndrome, and fibromyalgia. It was launched and marketed as Tramal by the German pharmaceutical company Grnenthal GmbH in 1977 (Wikipedia).
Structure
Data?1563866113
Synonyms
ValueSource
N,N,O-Tridesmethyl-tramadolHMDB
M4HMDB
Chemical FormulaC13H19NO2
Average Molecular Weight221.2955
Monoisotopic Molecular Weight221.141578857
IUPAC Name3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol
Traditional Name3-[(1R,2R)-2-(aminomethyl)-1-hydroxycyclohexyl]phenol
CAS Registry Number1235568-21-4
SMILES
NC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C13H19NO2/c14-9-11-4-1-2-7-13(11,16)10-5-3-6-12(15)8-10/h3,5-6,8,11,15-16H,1-2,4,7,9,14H2/t11-,13+/m1/s1
InChI KeyMJTYLDGVLFSXDG-YPMHNXCESA-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
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • 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 Solubility2 g/LALOGPS
logP1.31ALOGPS
logP0.68ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)9.84ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area66.48 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.72 m³·mol⁻¹ChemAxon
Polarizability24.57 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]+150.20831661259
DarkChem[M-H]-150.28531661259
DeepCCS[M+H]+155.22230932474
DeepCCS[M-H]-152.86430932474
DeepCCS[M-2H]-185.92130932474
DeepCCS[M+Na]+161.31530932474
AllCCS[M+H]+151.732859911
AllCCS[M+H-H2O]+147.732859911
AllCCS[M+NH4]+155.432859911
AllCCS[M+Na]+156.432859911
AllCCS[M-H]-154.832859911
AllCCS[M+Na-2H]-155.132859911
AllCCS[M+HCOO]-155.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N,N,O-TridesmethyltramadolNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C13074.6Standard polar33892256
N,N,O-TridesmethyltramadolNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12425.8Standard non polar33892256
N,N,O-TridesmethyltramadolNC[C@H]1CCCC[C@]1(O)C1=CC(O)=CC=C12142.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N,N,O-Tridesmethyltramadol,1TMS,isomer #1C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN2103.8Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,1TMS,isomer #2C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN)=C12078.0Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,1TMS,isomer #3C[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C12216.9Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN)=C12104.4Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #2C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O)=C12170.4Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #3C[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C)=C12185.8Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TMS,isomer #4C[Si](C)(C)N(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C2343.3Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C12166.8Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C12250.9Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #1C[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C12405.3Standard polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C2294.8Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C2445.8Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #2C[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C)[Si](C)(C)C2486.0Standard polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12321.1Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12422.4Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TMS,isomer #3C[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12567.7Standard polar33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12323.1Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12374.5Standard non polar33892256
N,N,O-Tridesmethyltramadol,4TMS,isomer #1C[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C)[Si](C)(C)C)=C12296.9Standard polar33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN2343.9Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN)=C12345.9Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C12463.7Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN)=C12543.0Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C12661.5Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12652.2Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C[C@H]1CCCC[C@]1(O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C2790.6Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12831.2Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12902.5Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC[C@H]1CCCC[C@]1(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C12706.5Standard polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2975.9Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3066.2Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@]1(C2=CC=CC(O)=C2)CCCC[C@@H]1CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2727.3Standard polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C13021.6Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C13050.7Standard non polar33892256
N,N,O-Tridesmethyltramadol,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12838.4Standard polar33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C13202.6Semi standard non polar33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C13145.6Standard non polar33892256
N,N,O-Tridesmethyltramadol,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=CC([C@@]2(O[Si](C)(C)C(C)(C)C)CCCC[C@@H]2CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C12664.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N,N,O-Tridesmethyltramadol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9710000000-268db0f1aebc53cd419f2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,N,O-Tridesmethyltramadol GC-MS (2 TMS) - 70eV, Positivesplash10-0unc-5089000000-6f445455f4595c2309522017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N,N,O-Tridesmethyltramadol 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,N,O-Tridesmethyltramadol 10V, Positive-QTOFsplash10-0zmr-0190000000-ad702816c9c637d766222017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Positive-QTOFsplash10-0k9i-4890000000-c83c71c810673bcf5fda2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Positive-QTOFsplash10-0pbl-9200000000-6f0d4a14c40ebdfbad512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Negative-QTOFsplash10-00di-0090000000-8d4804ac1b7c2b041c702017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Negative-QTOFsplash10-0fk9-6390000000-951c5a164c2b69ca54fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Negative-QTOFsplash10-0006-9710000000-6fce505a5e7437decb4a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Positive-QTOFsplash10-014i-9000000000-4d3180e05bafd704562f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Positive-QTOFsplash10-014i-9000000000-4d3180e05bafd704562f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Positive-QTOFsplash10-014i-9000000000-4d3180e05bafd704562f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 10V, Negative-QTOFsplash10-014i-9000000000-e1d016c3d6effe2294d22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 20V, Negative-QTOFsplash10-014i-9000000000-e1d016c3d6effe2294d22021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N,N,O-Tridesmethyltramadol 40V, Negative-QTOFsplash10-014i-9000000000-e1d016c3d6effe2294d22021-10-12Wishart 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 ID8395599
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10220107
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