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Record Information
Version4.0
Creation Date2013-07-22 19:50:02 UTC
Update Date2017-09-23 15:19:44 UTC
HMDB IDHMDB0061133
Secondary Accession Numbers
  • HMDB61133
Metabolite Identification
Common NameClofazimine glucuronide
DescriptionClofazimine glucuronide is a metabolite of clofazimine. Clofazimine is a fat-soluble riminophenazine dye used in combination with rifampicin and dapsone as multidrug therapy (MDT) for the treatment of leprosy. It has been used investigationally in combination with other antimycobacterial drugs to treat Mycobacterium avium infections in AIDS patients and Mycobacterium avium paratuberculosis infection in Crohn's disease patients. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H30Cl2N4O7
Average Molecular Weight665.52
Monoisotopic Molecular Weight664.149154748
IUPAC Name(2S,3S,4S,5R)-6-(2-{[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]-2,10-dihydrophenazin-2-ylidene]amino}propoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R)-6-(2-{[(2E)-10-(4-chlorophenyl)-3-[(4-chlorophenyl)amino]phenazin-2-ylidene]amino}propoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC(COC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)\N=C1/C=C2N(C3=CC=C(Cl)C=C3)C3=C(C=CC=C3)N=C2C=C1NC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C33H30Cl2N4O7/c1-17(16-45-33-30(42)28(40)29(41)31(46-33)32(43)44)36-24-15-27-25(14-23(24)37-20-10-6-18(34)7-11-20)38-22-4-2-3-5-26(22)39(27)21-12-8-19(35)9-13-21/h2-15,17,28-31,33,37,40-42H,16H2,1H3,(H,43,44)/b36-24+/t17?,28-,29-,30+,31-,33?/m0/s1
InChI KeyYJJBZADWPTXVOZ-DDXRKAPGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenazines and derivatives. These are polycyclic aromatic compounds containing a phenazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a pyrazine ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazanaphthalenes
Direct ParentPhenazines and derivatives
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • Phenazine
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Aniline or substituted anilines
  • Beta-hydroxy acid
  • Halobenzene
  • Chlorobenzene
  • Aryl chloride
  • Aryl halide
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrazine
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Secondary ketimine
  • Amino acid or derivatives
  • Amino acid
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organochloride
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug metabolite
  • Endogenous
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 Solubility0.026 mg/mLALOGPS
logP4.55ALOGPS
logP2.17ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)8.32ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area156.44 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity176.38 m3·mol-1ChemAxon
Polarizability68.23 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
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 IDDBMET00816
      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 LinkHMDB0061133
      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