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Record Information
Version3.6
Creation Date2013-06-15 17:01:38 UTC
Update Date2017-03-02 22:05:13 UTC
HMDB IDHMDB60577
Secondary Accession NumbersNone
Metabolite Identification
Common NameClomipramine N-oxide
DescriptionClomipramine N-oxide 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
SynonymsNot Available
Chemical FormulaC19H23ClN2O
Average Molecular Weight330.852
Monoisotopic Molecular Weight330.149891075
IUPAC Name3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}-N,N-dimethylpropanamine oxide
Traditional Name3-{14-chloro-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}-N,N-dimethylpropanamine oxide
CAS Registry NumberNot Available
SMILES
CN(C)(=O)CCCN1C2=CC=CC=C2CCC2=C1C=C(Cl)C=C2
InChI Identifier
InChI=1S/C19H23ClN2O/c1-22(2,23)13-5-12-21-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)21/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3
InChI KeyARNOTLDVJSFYBP-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
  • Trialkyl amine oxide
  • Tertiary amine
  • Trisubstituted n-oxide
  • N-oxide
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
Biofunction
  • Waste products
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 Solubility0.0013 mg/mLALOGPS
logP1.79ALOGPS
logP3.76ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area30.12 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.46 m3·mol-1ChemAxon
Polarizability36.86 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot 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 IDDBMET00817
      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
      NuGOwiki LinkHMDB60577
      Metagene LinkHMDB60577
      METLIN IDNot Available
      PubChem CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available