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Record Information
Version4.0
Creation Date2013-07-04 19:02:50 UTC
Update Date2017-09-27 08:43:55 UTC
HMDB IDHMDB0060840
Secondary Accession Numbers
  • HMDB60840
Metabolite Identification
Common NameN-Desmethyldoxepin
DescriptionN-Desmethyldoxepin is a metabolite of doxepin. Doxepin is a psychotropic agent with tricyclic antidepressant and anxiolytic properties, known under many brand-names such as Aponal, the original preparation by Boehringer-Mannheim, now part of the Roche group; Adapine, Doxal, Deptran, Sinquan and Sinequan. As doxepin hydrochloride, it is the active ingredient in cream-based preparations (Zonalon and Xepin) for the treatment of dermatological itch. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
DemethyldoxepinMeSH
Desmethyldoxepin, (e)-isomerMeSH
NordoxepinMeSH
DesmethyldoxepinMeSH
Desmethyldoxepin hydrochlorideMeSH
Desmethyldoxepin, (Z)-isomerMeSH
Chemical FormulaC18H19NO
Average Molecular Weight265.3496
Monoisotopic Molecular Weight265.146664235
IUPAC Namemethyl({3-[(2Z)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
Traditional Namemethyl({3-[(2Z)-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
CAS Registry Number58534-46-6
SMILES
CNCC\C=C1\C2=C(COC3=C1C=CC=C3)C=CC=C2
InChI Identifier
InChI=1S/C18H19NO/c1-19-12-6-10-16-15-8-3-2-7-14(15)13-20-18-11-5-4-9-17(16)18/h2-5,7-11,19H,6,12-13H2,1H3/b16-10-
InChI KeyHVKCEFHNSNZIHO-YBEGLDIGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzoxepines. These are compounds containing a dibenzoxepine moiety, which consists of two benzene connected by an oxazepine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzoxepines
Direct ParentDibenzoxepines
Alternative Parents
Substituents
  • Dibenzoxepine
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0036 g/LALOGPS
logP3.75ALOGPS
logP3.46ChemAxon
logS-4.9ALOGPS
pKa (Strongest Basic)10.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity92.95 m³·mol⁻¹ChemAxon
Polarizability30.87 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9140000000-c82077a7c3bebcc3a7e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0090000000-640c381a8a220acdd6a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-3190000000-3445698d3595ed148808View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9640000000-6a82b8594aa1a9414304View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-681052c04b852a0c46fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1090000000-c550628b634c6901a259View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053u-6190000000-5edfe7c7acd231e3e5e2View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Doxepin Metabolism PathwayPw000617Pw000617 greyscalePw000617 simpleNot Available
Displaying 1 entry
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00315
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB 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 Compound5353833
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available