Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-22 19:50:02 UTC
Update Date2021-09-14 15:40:21 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
Data?1563866149
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
Description Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Acetamide
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Ether
  • Azacycle
  • Organonitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.026 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity176.38 m³·mol⁻¹ChemAxon
Polarizability68.23 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+248.01530932474
DeepCCS[M-H]-246.29130932474
DeepCCS[M-2H]-280.32630932474
DeepCCS[M+Na]+254.31930932474
AllCCS[M+H]+245.232859911
AllCCS[M+H-H2O]+244.432859911
AllCCS[M+NH4]+245.832859911
AllCCS[M+Na]+246.032859911
AllCCS[M-H]-223.132859911
AllCCS[M+Na-2H]-224.432859911
AllCCS[M+HCOO]-226.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Clofazimine glucuronideCC(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=C17007.8Standard polar33892256
Clofazimine glucuronideCC(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=C14926.2Standard non polar33892256
Clofazimine glucuronideCC(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=C15678.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9210501000-f339cf9f0f786545e5732017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clofazimine glucuronide GC-MS (TMS_3_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 10V, Positive-QTOFsplash10-00rb-0000329000-735a213cca2a1430544b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 20V, Positive-QTOFsplash10-022l-0209731000-06d6e178c94572b134532017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 40V, Positive-QTOFsplash10-00dl-4207900000-ec9bad2cd6694f83510d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 10V, Negative-QTOFsplash10-03xr-2300309000-3dc680b774c10586656c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 20V, Negative-QTOFsplash10-002k-6900606000-0411f9ba9cbddc1fc3f02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 40V, Negative-QTOFsplash10-0bud-9500400000-7e0633735c47732f548d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 10V, Negative-QTOFsplash10-03di-0100109000-bc824a1319215f9d1d222021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 20V, Negative-QTOFsplash10-0a4i-2100915000-7b965ae7c2beaf6fdb292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 40V, Negative-QTOFsplash10-0540-9100310000-e2f0f1912b9c0d44c3e52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 10V, Positive-QTOFsplash10-00kb-0000209000-9bd71f98bb62441101ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 20V, Positive-QTOFsplash10-00di-0100923000-56c8e0bcaef3151305322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clofazimine glucuronide 40V, Positive-QTOFsplash10-0089-1000910000-b2e513de0d1739a7c5c12021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available