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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:08:55 UTC
Update Date2017-12-07 18:27:00 UTC
HMDB IDHMDB0060947
Secondary Accession Numbers
  • HMDB60947
Metabolite Identification
Common Namedesmethylclomipramine
Descriptiondesmethylclomipramine is a metabolite of clomipramine. Clomipramine (trademarked as Anafranil) is a tricyclic antidepressant (TCA). It was developed in the 1960s by the Swiss drug manufacturer Geigy (now known as Novartis) and has been in clinical use worldwide ever since. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
N-DemethylclomipramineMeSH
Desmethylclomipramine hydrochlorideMeSH
DemethylchlorimipramineMeSH
DesmethylchlorimipramineMeSH
Chemical FormulaC18H21ClN2
Average Molecular Weight300.826
Monoisotopic Molecular Weight300.139326389
IUPAC Name(3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)(methyl)amine
Traditional Name(3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)(methyl)amine
CAS Registry Number303-48-0
SMILES
CNCCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2
InChI Identifier
InChI=1S/C18H21ClN2/c1-20-11-4-12-21-17-6-3-2-5-14(17)7-8-15-9-10-16(19)13-18(15)21/h2-3,5-6,9-10,13,20H,4,7-8,11-12H2,1H3
InChI KeyVPIXQGUBUKFLRF-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
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Tertiary amine
  • Secondary amine
  • Secondary aliphatic amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic nitrogen 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 Solubility0.0093 g/LALOGPS
logP4.43ALOGPS
logP4.5ChemAxon
logS-4.5ALOGPS
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area15.27 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.12 m³·mol⁻¹ChemAxon
Polarizability34.35 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, Positivesplash10-0006-6090000000-9eed19a2ef45fc520c90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-1069000000-86dede74ad37de04b372View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-6093000000-595de34abeb5c6686672View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9240000000-ac7e79f4ac427320c754View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-f1e765f5a26c70ab77d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-1090000000-1ddc75254b4387dae329View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fbc-2390000000-bb1e61bf6aeb82c055f0View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Clomipramine Metabolism PathwayPw000615Pw000615 greyscalePw000615 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 IDDBMET00244
      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 Compound622606
      PDB IDNot Available
      ChEBI ID124969
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available