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Record Information
Version4.0
Creation Date2013-07-09 16:06:11 UTC
Update Date2017-09-27 08:43:56 UTC
HMDB IDHMDB0060901
Secondary Accession Numbers
  • HMDB60901
Metabolite Identification
Common NameClozapine glucuronide
DescriptionClozapine glucuronide is a metabolite of clozapine. Clozapine (sold as Clozaril, Gen-Clozapine in Canada, Azaleptin, Leponex, Fazaclo, Froidir; Denzapine, Zaponex in the UK; Klozapol in Poland, Clopine in Australia and New Zealand) is an atypical antipsychotic medication used in the treatment of schizophrenia, and is also used off-label in the treatment of bipolar disorder. Wyatt. R and Chew. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC24H27ClN4O6
Average Molecular Weight502.947
Monoisotopic Molecular Weight502.161912323
IUPAC Name(2R,3R,4R,5S,6S)-6-[6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2R,3R,4R,5S,6S)-6-[6-chloro-10-(4-methylpiperazin-1-yl)-2,9-diazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,9,11,13-heptaen-2-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CN1CCN(CC1)C1=NC2=C(C=CC(Cl)=C2)N([C@H]2O[C@H]([C@H](O)[C@@H](O)[C@@H]2O)C(O)=O)C2=CC=CC=C12
InChI Identifier
InChI=1S/C24H27ClN4O6/c1-27-8-10-28(11-9-27)22-14-4-2-3-5-16(14)29(17-7-6-13(25)12-15(17)26-22)23-20(32)18(30)19(31)21(35-23)24(33)34/h2-7,12,18-21,23,30-32H,8-11H2,1H3,(H,33,34)/t18-,19-,20+,21-,23+/m1/s1
InChI KeyYWWIDMPXCSUNRD-VZWAGXQNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzodiazepines. These are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzodiazepines
Direct ParentDibenzodiazepines
Alternative Parents
Substituents
  • Dibenzodiazepine
  • N-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Alkyldiarylamine
  • N-glycosyl compound
  • Glycosyl compound
  • 1,4-benzodiazepine
  • N-alkylpiperazine
  • N-methylpiperazine
  • Beta-hydroxy acid
  • Hydroxy acid
  • Aryl halide
  • Imidolactam
  • Monosaccharide
  • 1,4-diazinane
  • Benzenoid
  • Oxane
  • Piperazine
  • Pyran
  • Aryl chloride
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Amino acid
  • Amino acid or derivatives
  • Amidine
  • Carboxylic acid amidine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organonitrogen 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 Solubility0.56 g/LALOGPS
logP1.12ALOGPS
logP-1.2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)2.91ChemAxon
pKa (Strongest Basic)7.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity129.78 m³·mol⁻¹ChemAxon
Polarizability51.03 ųChemAxon
Number of Rings5ChemAxon
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 (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0002970000-c24223d4da8e082ee1f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-7207910000-c340c2dc5c205f11ef8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-1049100000-0108f71fb5bb73f6598dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0105790000-24032d67472d4f026db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00mt-0009100000-8f12f643cd8f30000a17View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8429000000-d2e9d61785df0ee41385View 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 IDDBMET00102
      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