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Record Information
Version4.0
Creation Date2013-07-09 16:09:11 UTC
Update Date2017-09-27 08:43:57 UTC
HMDB IDHMDB0060952
Secondary Accession Numbers
  • HMDB60952
Metabolite Identification
Common Name2-hydroxyimipramine
Description2-hydroxyimipramine is a metabolite of imipramine. Imipramine (sold as Antideprin, Deprimin, Deprinol, Depsol, Depsonil, Dynaprin, Eupramin, Imipramil, Irmin, Janimine, Melipramin, Surplix, Tofranil), also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group. Imipramine is mainly used in the treatment of major depression and enuresis (inability to control urination). It has also been evaluated for use in panic disorder. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
2-Hydroxyimipramine hydrochlorideMeSH
Chemical FormulaC19H24N2O
Average Molecular Weight296.4067
Monoisotopic Molecular Weight296.1888634
IUPAC Name2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
Traditional Name2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-6-ol
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=CC=CC=C2CCC2=CC(O)=CC=C12
InChI Identifier
InChI=1S/C19H24N2O/c1-20(2)12-5-13-21-18-7-4-3-6-15(18)8-9-16-14-17(22)10-11-19(16)21/h3-4,6-7,10-11,14,22H,5,8-9,12-13H2,1-2H3
InChI KeyROTCPJFWLNDKHU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Alkyldiarylamine
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • 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 Solubility0.23 g/LALOGPS
logP3.83ALOGPS
logP3.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)10.53ChemAxon
pKa (Strongest Basic)9.18ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.71 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.59 m³·mol⁻¹ChemAxon
Polarizability34.41 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-8d8c8134a93148bda232View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f72-6090000000-ef333add7ecb6afc412eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-007c-9220000000-a094728c7b1d6bd6e324View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-cbcfaec215c09531c84fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-0090000000-68ffadf8b3d60843ff7bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3690000000-f0d1657cbf38e63ff3daView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Imipramine Metabolism PathwayPw000601Pw000601 greyscalePw000601 simpleNot Available
Imipramine PathwayPw000424Pw000424 greyscalePw000424 simpleNot Available
Displaying all 2 entries
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 IDDBMET00254
      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 Compound108051
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available