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Record Information
Version4.0
Creation Date2013-07-22 19:50:57 UTC
Update Date2017-09-27 08:44:02 UTC
HMDB IDHMDB0061147
Secondary Accession Numbers
  • HMDB61147
Metabolite Identification
Common NameHydroxyclomipramine glucuronide
DescriptionHydroxyclomipramine glucuronide 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 FormulaC25H31ClN2O7
Average Molecular Weight506.976
Monoisotopic Molecular Weight506.181979063
IUPAC Name(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-({14-chloro-2-[3-(dimethylamino)propyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-7-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN(C)CCCN1C2=C(CCC3=C1C=CC=C3O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=CC(Cl)=C2
InChI Identifier
InChI=1S/C25H31ClN2O7/c1-27(2)11-4-12-28-17-5-3-6-19(16(17)10-8-14-7-9-15(26)13-18(14)28)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h3,5-7,9,13,20-23,25,29-31H,4,8,10-12H2,1-2H3,(H,32,33)/t20-,21-,22+,23-,25+/m0/s1
InChI KeyKLJBBCVPINUDOY-LYVDORBWSA-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
  • Phenolic glycoside
  • Dibenzazepine
  • O-glucuronide
  • 1-o-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Alkyldiarylamine
  • O-glycosyl compound
  • Glycosyl compound
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Beta-hydroxy acid
  • Aryl chloride
  • Aryl halide
  • Monosaccharide
  • Hydroxy acid
  • Oxane
  • Pyran
  • Benzenoid
  • Amino acid
  • Amino acid or derivatives
  • Secondary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 Solubility0.79 g/LALOGPS
logP2.58ALOGPS
logP-0.1ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.05ChemAxon
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area122.93 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity129.4 m³·mol⁻¹ChemAxon
Polarizability51.64 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0a4l-9201300000-e5f85473637aac2ed6ffView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-052r-9310055000-c2dc3e23eadaf56792b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001r-1009530000-bb158b41508b9058d7b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m0-2029000000-6935d7084d3d6127faf2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001c-9365000000-cbde462b3ed78c8f6a03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-2309680000-d44cbc1464081a6f4a0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1219300000-cdc0c66802d6c9b0055eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-5198000000-3ffe3b8bb19a525d6584View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
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 IDDBMET00871
      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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available