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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:01:37 UTC
Update Date2021-09-14 14:58:38 UTC
HMDB IDHMDB0014257
Secondary Accession Numbers
  • HMDB14257
Metabolite Identification
Common NameE-10-Hydroxydesmethylnortriptyline
DescriptionE-10-Hydroxydesmethylnortriptyline belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. E-10-Hydroxydesmethylnortriptyline is a very strong basic compound (based on its pKa). E-10-Hydroxydesmethylnortriptyline is only found in individuals that have used or taken Amitriptyline. E-10-Hydroxydesmethylnortriptyline is a metabolite of Amitriptyline. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene connected by a cycloheptene ring.
Structure
Data?1582753163
SynonymsNot Available
Chemical FormulaC18H19NO
Average Molecular Weight265.3496
Monoisotopic Molecular Weight265.146664235
IUPAC Name(2E)-2-(3-aminopropylidene)tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol
Traditional Name(2E)-2-(3-aminopropylidene)tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-9-ol
CAS Registry NumberNot Available
SMILES
NCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C18H19NO/c19-11-5-10-15-14-7-2-1-6-13(14)12-18(20)17-9-4-3-8-16(15)17/h1-4,6-10,18,20H,5,11-12,19H2/b15-10+
InChI KeyPIEVJGJKDMQGSG-XNTDXEJSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassDibenzocycloheptenes
Sub ClassNot Available
Direct ParentDibenzocycloheptenes
Alternative Parents
Substituents
  • Dibenzocycloheptene
  • Secondary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • 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 Solubility0.016 g/LALOGPS
logP2.88ALOGPS
logP2.76ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)14.26ChemAxon
pKa (Strongest Basic)10.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area46.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.95 m³·mol⁻¹ChemAxon
Polarizability30.37 ųChemAxon
Number of Rings3ChemAxon
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]+164.19831661259
DarkChem[M-H]-162.90731661259
DeepCCS[M-2H]-195.83230932474
DeepCCS[M+Na]+171.39830932474
AllCCS[M+H]+164.232859911
AllCCS[M+H-H2O]+160.632859911
AllCCS[M+NH4]+167.532859911
AllCCS[M+Na]+168.532859911
AllCCS[M-H]-168.432859911
AllCCS[M+Na-2H]-168.132859911
AllCCS[M+HCOO]-167.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
E-10-HydroxydesmethylnortriptylineNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C123461.5Standard polar33892256
E-10-HydroxydesmethylnortriptylineNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C122499.6Standard non polar33892256
E-10-HydroxydesmethylnortriptylineNCC\C=C1/C2=CC=CC=C2CC(O)C2=CC=CC=C122421.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
E-10-Hydroxydesmethylnortriptyline,1TMS,isomer #1C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN)C2=CC=CC=C212475.4Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,1TMS,isomer #2C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C122650.7Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C122594.4Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C122572.1Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #1C[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C)C2=CC=CC=C123088.2Standard polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C2837.2Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C2840.9Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TMS,isomer #2C[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C3234.3Standard polar33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C212756.6Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C212800.3Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,3TMS,isomer #1C[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C)[Si](C)(C)C)C2=CC=CC=C212984.4Standard polar33892256
E-10-Hydroxydesmethylnortriptyline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN)C2=CC=CC=C212732.9Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C122906.8Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C123018.2Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C123059.4Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)NCC/C=C1\C2=CC=CC=C2CC(O[Si](C)(C)C(C)(C)C)C2=CC=CC=C123239.6Standard polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3276.9Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3268.3Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(CC/C=C1\C2=CC=CC=C2CC(O)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C3316.0Standard polar33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C213432.0Semi standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C213464.1Standard non polar33892256
E-10-Hydroxydesmethylnortriptyline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1CC2=CC=CC=C2/C(=C\CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C2=CC=CC=C213156.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - E-10-Hydroxydesmethylnortriptyline GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9380000000-7f30b4b3e8709cb182ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - E-10-Hydroxydesmethylnortriptyline GC-MS (1 TMS) - 70eV, Positivesplash10-0089-9043000000-bafab0c3999454f81cca2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - E-10-Hydroxydesmethylnortriptyline 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 - E-10-Hydroxydesmethylnortriptyline 10V, Negative-QTOFsplash10-03di-0090000000-726dea79d4f611bf635c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Negative-QTOFsplash10-03di-0090000000-8b7a42c41e2e29c52b9c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Negative-QTOFsplash10-00kp-4090000000-f5ce19cf845fa393bbf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Negative-QTOFsplash10-03di-0090000000-f88a9abb5979da4e772d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Negative-QTOFsplash10-08fr-0190000000-df21930d302d46ec80ba2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Negative-QTOFsplash10-014i-1290000000-9f66f0bc1f7554e477e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Positive-QTOFsplash10-00kb-0090000000-0e6ec8b5602840a753212016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Positive-QTOFsplash10-000t-1090000000-cd2d0e452aa79e6f3b402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Positive-QTOFsplash10-0a5c-5390000000-506657e81c957c8770db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 10V, Positive-QTOFsplash10-014i-0090000000-d7e2674b434ca547f3f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 20V, Positive-QTOFsplash10-00lr-0090000000-9fd9be8a426b1ce80dc42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - E-10-Hydroxydesmethylnortriptyline 40V, Positive-QTOFsplash10-0a4i-1490000000-4b9a8cf7590226dbc5692021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry 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 ID5005861
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6506716
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