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Record Information
StatusExpected but not Quantified
Creation Date2013-06-15 18:09:01 UTC
Update Date2017-12-07 17:30:38 UTC
Secondary Accession Numbers
  • HMDB60624
Metabolite Identification
Common NameEthionamide sulphoxide
DescriptionEthionamide sulphoxide is a metabolite of ethionamide. Ethionamide (2-ethylthioisonicotinamide, Trecator SC) is an antibiotic used in the treatment of tuberculosis. Ethionamide works to induce expression of EthA, a NAD derivative which is toxic to fungi. The resistance mechanism of this drug is through EthR, resistance is common. Therefore, EthR inhibitors are of great interest. It is a prodrug. It has been proposed for use in combination with gatifloxacin. The action may be through disruption of mycolic acid. (Wikipedia)
Ethionamide sulfoxideChEBI
Ethionamide sulphoxideChEBI
Chemical FormulaC8H10N2OS
Average Molecular Weight182.243
Monoisotopic Molecular Weight182.051383642
IUPAC Name(2-ethylpyridin-4-yl)(sulfinylidene)methanamine
Traditional Name(2-ethylpyridin-4-yl)(sulfinylidene)methanamine
CAS Registry NumberNot Available
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
  • Pyridine
  • Heteroaromatic compound
  • Azacycle
  • Sulfinyl compound
  • Sulfine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Biological location:


  Biofluid and excreta:

  Organ and components:



Biological role:

Physical Properties
StateNot Available
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility71.3 g/LALOGPS
pKa (Strongest Acidic)7.53ChemAxon
pKa (Strongest Basic)4.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.98 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.95 m³·mol⁻¹ChemAxon
Polarizability18.62 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-2900000000-e1e57c15859b4306c6bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0900000000-cc0dcc80ecd495acbefaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-20f6be49e087dc9c38dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9600000000-3c6a5f1dedd78e140dc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-8862d0db3ba360dc524aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900000000-c674145c3a95a060d127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fs-9100000000-2eeb13718a3e3f1a0466View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound 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 Compound71316501
      PDB IDNot Available
      ChEBI ID87805
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Deshpande AY, Gurav S, Punde R, Zambre V, Kulkarni R, Pandey S, Mungantiwar A, Mullangi R: Development and validation of a highly sensitive LC-MS/MS method for simultaneous quantitation of ethionamide and ethionamide sulfoxide in human plasma: application to a human pharmacokinetic study. Biomed Chromatogr. 2011 Sep;25(9):985-94. doi: 10.1002/bmc.1554. Epub 2011 Jan 26. [PubMed:21268048 ]
      2. Grunert M, Werner E, Iwainsky H, Eule H: [Associated chemical and microbiological studies on the antitubercular properties of ethionamide sulfoxide]. Z Erkr Atmungsorgane Folia Bronchol. 1970 Dec;133(1):406-8. [PubMed:5204733 ]
      3. Bieder A, Brunel P, Roquet-Ghaye J, Kreis B: [Evolution of serum concentrations of ethionamide (TH 1413) and ethionamide sulfoxide (TH 1405) after oral administration of these tuberculostatic agents in man]. Rev Fr Etud Clin Biol. 1966 Apr;11(4):419-23. [PubMed:5944589 ]