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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-06-15 18:11:23 UTC
Update Date2017-12-07 17:32:17 UTC
HMDB IDHMDB0060630
Secondary Accession Numbers
  • HMDB60630
Metabolite Identification
Common Name(E)-2-hydroxydoxepin
Description(E)-2-hydroxydoxepin 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
SynonymsNot Available
Chemical FormulaC19H21NO2
Average Molecular Weight295.3755
Monoisotopic Molecular Weight295.157228921
IUPAC Name(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol
Traditional Name(2Z)-2-[3-(dimethylamino)propylidene]-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-5-ol
CAS Registry NumberNot Available
SMILES
CN(C)CC\C=C1/C2=CC(O)=CC=C2OCC2=C1C=CC=C2
InChI Identifier
InChI=1S/C19H21NO2/c1-20(2)11-5-8-17-16-7-4-3-6-14(16)13-22-19-10-9-15(21)12-18(17)19/h3-4,6-10,12,21H,5,11,13H2,1-2H3/b17-8-
InChI KeyGRQPGTWGEQWMMM-IUXPMGMMSA-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Oxacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.13 g/LALOGPS
logP3.84ALOGPS
logP2.94ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.07ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.7 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.23 m³·mol⁻¹ChemAxon
Polarizability33.67 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, Positivesplash10-0a4i-9040000000-44dc41d6196461d8e9dfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-9013000000-1ada3fa3f839a5c6b22eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-3c7af17ff121e45167ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgj-3190000000-f5340f8dd9219b60367cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbc-9360000000-dbfa51b8e3061560faefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0090000000-a29aa17b53d506431541View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0090000000-e92584307aa000c1ec71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-3290000000-cdb65e536dc863ad82b6View 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
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 IDDBMET00873
      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 Compound67319009
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available