Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2013-06-15 18:09:01 UTC |
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Update Date | 2023-02-21 17:30:06 UTC |
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HMDB ID | HMDB0060624 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Ethionamide sulphoxide |
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Description | Ethionamide 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) |
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Structure | InChI=1S/C8H10N2OS/c1-2-7-5-6(3-4-10-7)8(9)12-11/h3-5H,2,9H2,1H3 |
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Synonyms | Value | Source |
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Ethionamide sulfoxide | ChEBI | Ethionamide sulphoxide | ChEBI |
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Chemical Formula | C8H10N2OS |
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Average Molecular Weight | 182.243 |
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Monoisotopic Molecular Weight | 182.051383642 |
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IUPAC Name | (2-ethylpyridin-4-yl)(sulfinylidene)methanamine |
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Traditional Name | (2-ethylpyridin-4-yl)(sulfinylidene)methanamine |
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CAS Registry Number | Not Available |
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SMILES | CCC1=NC=CC(=C1)C(N)=S=O |
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InChI Identifier | InChI=1S/C8H10N2OS/c1-2-7-5-6(3-4-10-7)8(9)12-11/h3-5H,2,9H2,1H3 |
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InChI Key | QDQQNGZRIJPDGA-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Not Available |
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Direct Parent | Pyridines and derivatives |
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Alternative Parents | |
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Substituents | - 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
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Ethionamide sulphoxide,1TMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1 | 1921.4 | Semi standard non polar | 33892256 | Ethionamide sulphoxide,1TMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1 | 1592.2 | Standard non polar | 33892256 | Ethionamide sulphoxide,1TMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C)=S=O)=CC=N1 | 2638.7 | Standard polar | 33892256 | Ethionamide sulphoxide,2TMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1 | 1957.3 | Semi standard non polar | 33892256 | Ethionamide sulphoxide,2TMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1 | 1770.9 | Standard non polar | 33892256 | Ethionamide sulphoxide,2TMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C)[Si](C)(C)C)=CC=N1 | 2308.1 | Standard polar | 33892256 | Ethionamide sulphoxide,1TBDMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1 | 2158.7 | Semi standard non polar | 33892256 | Ethionamide sulphoxide,1TBDMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1 | 1819.7 | Standard non polar | 33892256 | Ethionamide sulphoxide,1TBDMS,isomer #1 | CCC1=CC(C(N[Si](C)(C)C(C)(C)C)=S=O)=CC=N1 | 2696.9 | Standard polar | 33892256 | Ethionamide sulphoxide,2TBDMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1 | 2439.7 | Semi standard non polar | 33892256 | Ethionamide sulphoxide,2TBDMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1 | 2193.7 | Standard non polar | 33892256 | Ethionamide sulphoxide,2TBDMS,isomer #1 | CCC1=CC(C(=S=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=N1 | 2433.9 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Ethionamide sulphoxide GC-MS (Non-derivatized) - 70eV, Positive | splash10-001i-2900000000-e1e57c15859b4306c6bf | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Ethionamide sulphoxide GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Positive-QTOF | splash10-00lr-0900000000-cc0dcc80ecd495acbefa | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Positive-QTOF | splash10-00lr-0900000000-20f6be49e087dc9c38db | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Positive-QTOF | splash10-0a6r-9600000000-3c6a5f1dedd78e140dc1 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Negative-QTOF | splash10-001i-0900000000-8862d0db3ba360dc524a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Negative-QTOF | splash10-001i-3900000000-c674145c3a95a060d127 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Negative-QTOF | splash10-00fs-9100000000-2eeb13718a3e3f1a0466 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Positive-QTOF | splash10-001i-0900000000-9e05192d1bd755c0f756 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Positive-QTOF | splash10-001i-0900000000-cffdf45561ef57a7f9a8 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Positive-QTOF | splash10-0a4i-9500000000-8afdbc66318c758b4af0 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 10V, Negative-QTOF | splash10-001i-1900000000-7774abd10ade777d372b | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 20V, Negative-QTOF | splash10-003s-9700000000-7e99e9e2a9cbcc30de98 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Ethionamide sulphoxide 40V, Negative-QTOF | splash10-004j-9200000000-eb1791a4bad974853ef9 | 2021-10-12 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-04 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-04 | FELIX lab | View Spectrum |
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General References | - 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 ]
- 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 ]
- 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 ]
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