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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:05:33 UTC
Update Date2019-07-23 07:15:19 UTC
HMDB IDHMDB0060891
Secondary Accession Numbers
  • HMDB60891
Metabolite Identification
Common NameN-Desmethylterbinafine
DescriptionN-Desmethylterbinafine belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. N-Desmethylterbinafine is a very strong basic compound (based on its pKa). It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. N-Desmethylterbinafine is a metabolite of terbinafine. Terbinafine hydrochloride is a synthetic allylamine antifungal from Novartis.
Structure
Data?1563866119
Synonyms
ValueSource
Desmethylterbinafine, (e)-isomerHMDB
Desmethylterbinafine hydrochloride, (e)-isomerHMDB
DesmethylterbinafineMeSH
Chemical FormulaC20H23N
Average Molecular Weight277.4033
Monoisotopic Molecular Weight277.183049741
IUPAC Name[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine
Traditional Name[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](naphthalen-1-ylmethyl)amine
CAS Registry NumberNot Available
SMILES
CC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C20H23N/c1-20(2,3)14-7-4-8-15-21-16-18-12-9-11-17-10-5-6-13-19(17)18/h4-6,8-13,21H,15-16H2,1-3H3/b8-4+
InChI KeyIZJZLXQHMWUCIC-XBXARRHUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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 Solubility0.00071 g/LALOGPS
logP5.5ALOGPS
logP5.14ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)9.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity92.78 m³·mol⁻¹ChemAxon
Polarizability33.78 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+172.4431661259
DarkChem[M-H]-173.47531661259
DeepCCS[M-2H]-196.88630932474
DeepCCS[M+Na]+172.45230932474
AllCCS[M+H]+167.832859911
AllCCS[M+H-H2O]+164.532859911
AllCCS[M+NH4]+170.932859911
AllCCS[M+Na]+171.832859911
AllCCS[M-H]-176.232859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-175.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-DesmethylterbinafineCC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C123163.1Standard polar33892256
N-DesmethylterbinafineCC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C122384.9Standard non polar33892256
N-DesmethylterbinafineCC(C)(C)C#C\C=C\CNCC1=CC=CC2=CC=CC=C122327.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Desmethylterbinafine,1TMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2318.0Semi standard non polar33892256
N-Desmethylterbinafine,1TMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C2495.1Standard non polar33892256
N-Desmethylterbinafine,1TMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C3190.2Standard polar33892256
N-Desmethylterbinafine,1TBDMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2556.2Semi standard non polar33892256
N-Desmethylterbinafine,1TBDMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C2682.7Standard non polar33892256
N-Desmethylterbinafine,1TBDMS,isomer #1CC(C)(C)C#C/C=C/CN(CC1=CC=CC2=CC=CC=C12)[Si](C)(C)C(C)(C)C3260.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethylterbinafine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-1930000000-cd75c3521c488cd064412017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Desmethylterbinafine 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-Desmethylterbinafine 10V, Positive-QTOFsplash10-004l-0790000000-48cf9a06ce59d2b5cec92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Positive-QTOFsplash10-0006-0910000000-7dd31856f24ef0b939572017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Positive-QTOFsplash10-0006-2900000000-8576e3e9be60701990042017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Negative-QTOFsplash10-004i-0190000000-a2cc4270b6d348b87c9c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Negative-QTOFsplash10-056r-0980000000-d7b29ca9e90d2e10614a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Negative-QTOFsplash10-056r-0900000000-b30cc7379173d05ec4fd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Positive-QTOFsplash10-0006-0930000000-f6db78b9e73cd09bed172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Positive-QTOFsplash10-004i-3940000000-8d1d265c93e478ef1ef62021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Positive-QTOFsplash10-0006-5900000000-d4a57ea4dff3a9f5ef362021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 10V, Negative-QTOFsplash10-004i-0090000000-c524df0015f139e69d142021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 20V, Negative-QTOFsplash10-004i-0690000000-d35bfcf98df5aa8e75672021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Desmethylterbinafine 40V, Negative-QTOFsplash10-0fbc-0910000000-6f3bd0a35275de042a7a2021-10-12Wishart 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 Compound6443233
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