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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-15 17:59:28 UTC
Update Date2023-02-21 17:30:06 UTC
HMDB IDHMDB0060611
Secondary Accession Numbers
  • HMDB60611
Metabolite Identification
Common NameN-Desmethyl tapentadol
DescriptionN-Desmethyl tapentadol is a metabolite of tapentadol. Tapentadol (trade name Nucynta, Palexia, In India - ZYNTAP) is a centrally acting analgesic with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor. It is also an agonist of the σ2 receptor, though the function of this orphan receptor remains controversial. While its analgesic actions have been compared to tramadol and oxycodone, its general potency is somewhere between tramadol and morphine in effectiveness. (Wikipedia)
Structure
Data?1677000606
SynonymsNot Available
Chemical FormulaC13H21NO
Average Molecular Weight207.3119
Monoisotopic Molecular Weight207.162314299
IUPAC Name3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenol
Traditional Name3-[(2R,3R)-2-methyl-1-(methylamino)pentan-3-yl]phenol
CAS Registry NumberNot Available
SMILES
CC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C13H21NO/c1-4-13(10(2)9-14-3)11-6-5-7-12(15)8-11/h5-8,10,13-15H,4,9H2,1-3H3/t10-,13+/m0/s1
InChI KeyPQQINTFVECNXLC-GXFFZTMASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Phenol
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
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 Solubility0.21 g/LALOGPS
logP2.54ALOGPS
logP2.31ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.88ChemAxon
pKa (Strongest Basic)10.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.26 m³·mol⁻¹ChemAxon
Polarizability24.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+152.22731661259
DarkChem[M-H]-152.41231661259
DeepCCS[M+H]+155.30630932474
DeepCCS[M-H]-152.94830932474
DeepCCS[M-2H]-185.83430932474
DeepCCS[M+Na]+161.39930932474
AllCCS[M+H]+148.632859911
AllCCS[M+H-H2O]+144.632859911
AllCCS[M+NH4]+152.232859911
AllCCS[M+Na]+153.332859911
AllCCS[M-H]-153.532859911
AllCCS[M+Na-2H]-154.432859911
AllCCS[M+HCOO]-155.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-Desmethyl tapentadolCC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C12405.9Standard polar33892256
N-Desmethyl tapentadolCC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C11675.7Standard non polar33892256
N-Desmethyl tapentadolCC[C@H]([C@@H](C)CNC)C1=CC(O)=CC=C11719.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desmethyl tapentadol,1TMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CNC1712.7Semi standard non polar33892256
N-Desmethyl tapentadol,1TMS,isomer #2CC[C@@H](C1=CC=CC(O)=C1)[C@@H](C)CN(C)[Si](C)(C)C1853.0Semi standard non polar33892256
N-Desmethyl tapentadol,2TMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C1893.0Semi standard non polar33892256
N-Desmethyl tapentadol,2TMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C1853.5Standard non polar33892256
N-Desmethyl tapentadol,2TMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C1938.6Standard polar33892256
N-Desmethyl tapentadol,1TBDMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CNC1924.7Semi standard non polar33892256
N-Desmethyl tapentadol,1TBDMS,isomer #2CC[C@@H](C1=CC=CC(O)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C2072.0Semi standard non polar33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C2359.4Semi standard non polar33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C2267.5Standard non polar33892256
N-Desmethyl tapentadol,2TBDMS,isomer #1CC[C@@H](C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](C)CN(C)[Si](C)(C)C(C)(C)C2216.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl tapentadol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-6900000000-0af3df485ff0f1784f132017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl tapentadol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-7190000000-35a34444c7a1d3bb218e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethyl tapentadol 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-Desmethyl tapentadol 10V, Positive-QTOFsplash10-0a4i-0590000000-02b28b801bf1f394f7282017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Positive-QTOFsplash10-056r-2920000000-f880e1ba8c383a501ede2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Positive-QTOFsplash10-01pt-3900000000-de5fabc0f31ad185455d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Negative-QTOFsplash10-0a4i-0090000000-f2e10f92ad48359661ef2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Negative-QTOFsplash10-0a4i-0190000000-53c865ea33ae3b8b62e72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Negative-QTOFsplash10-03dl-4900000000-f96465ec77dce21f6c8a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Negative-QTOFsplash10-0a4i-0090000000-7e132929fbdc86d412d82021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Negative-QTOFsplash10-0a4i-0390000000-476db1208340c854c5d42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Negative-QTOFsplash10-0a4i-2900000000-4eba01fce891da694dbb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 10V, Positive-QTOFsplash10-0a4i-3890000000-484c12dfc97c39894ced2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 20V, Positive-QTOFsplash10-05c5-9610000000-795f772a77e1b997b53e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethyl tapentadol 40V, Positive-QTOFsplash10-069s-9800000000-6b7ebd7f074cc9d028a22021-10-12Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71159880
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