Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2021-09-07 16:45:29 UTC |
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HMDB ID | HMDB0001368 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 3-Mercaptopyruvic acid |
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Description | 3-Mercaptopyruvic acid, also known as 3-mercapto-2-oxopropanoate or beta-thiopyruvate, belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. 3-Mercaptopyruvic acid is an intermediate in cysteine metabolism. 3-Mercaptopyruvic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3-mercaptopyruvic acid participates in a number of enzymatic reactions. In particular, 3-mercaptopyruvic acid and cyanide can be converted into pyruvic acid and thiocyanate; which is mediated by the enzyme 3-mercaptopyruvate sulfurtransferase. In addition, 3-mercaptopyruvic acid can be biosynthesized from 3-mercaptolactic acid; which is mediated by the enzyme L-lactate dehydrogenase. It has been studied as a potential treatment for cyanide poisoning, but its half-life is too short for it to be clinically effective. In humans, 3-mercaptopyruvic acid is involved in cystinosis, ocular nonnephropathic. Outside of the human body, 3-mercaptopyruvic acid has been detected, but not quantified in several different foods, such as lima beans, spinachs, shallots, mexican groundcherries, and white lupines. This could make 3-mercaptopyruvic acid a potential biomarker for the consumption of these foods. |
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Structure | InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6) |
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Synonyms | Value | Source |
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3-Mercapto-2-oxopropanoic acid | ChEBI | 3-Mercaptopyruvate | ChEBI | Mercaptopyruvate | ChEBI | 3-Mercapto-2-oxopropanoate | Generator | Mercaptopyruvic acid | Generator | 3-Mercapto-pyruvate | HMDB | 3-Mercapto-pyruvic acid | HMDB | beta-3-Mercapto-2-oxo-propanoate | HMDB | beta-3-Mercapto-2-oxo-propanoic acid | HMDB | beta-Mercaptopyruvate | HMDB | beta-Mercaptopyruvic acid | HMDB | beta-Thiopyruvate | HMDB | beta-Thiopyruvic acid | HMDB | Thiopyruvate | HMDB | 3-Mercaptopyruvate monosodium salt | HMDB |
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Chemical Formula | C3H4O3S |
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Average Molecular Weight | 120.127 |
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Monoisotopic Molecular Weight | 119.988114684 |
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IUPAC Name | 2-oxo-3-sulfanylpropanoic acid |
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Traditional Name | β-mercaptopyruvic acid |
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CAS Registry Number | 2464-23-5 |
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SMILES | OC(=O)C(=O)CS |
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InChI Identifier | InChI=1S/C3H4O3S/c4-2(1-7)3(5)6/h7H,1H2,(H,5,6) |
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InChI Key | OJOLFAIGOXZBCI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alpha-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Keto acids and derivatives |
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Sub Class | Alpha-keto acids and derivatives |
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Direct Parent | Alpha-keto acids and derivatives |
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Alternative Parents | |
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Substituents | - Alpha-keto acid
- Alpha-hydroxy ketone
- Ketone
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alkylthiol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organosulfur compound
- Organooxygen compound
- Carbonyl group
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect
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Adverse health effect
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Disposition
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Biological location
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Process
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Naturally occurring process
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Physical Properties |
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State | Solid |
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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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3-Mercaptopyruvic acid,1TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=O)CS | 1154.9 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,1TMS,isomer #2 | C[Si](C)(C)SCC(=O)C(=O)O | 1329.6 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,1TMS,isomer #3 | C[Si](C)(C)OC(=CS)C(=O)O | 1304.1 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C | 1433.2 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C | 1379.7 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C | 1509.4 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C | 1467.7 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C | 1462.3 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C | 1478.6 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O | 1530.1 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O | 1527.9 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TMS,isomer #3 | C[Si](C)(C)OC(=CS[Si](C)(C)C)C(=O)O | 1696.9 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C | 1565.2 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C | 1471.0 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C)O[Si](C)(C)C | 1516.9 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS | 1417.6 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)SCC(=O)C(=O)O | 1585.6 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=CS)C(=O)O | 1542.2 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C | 1883.1 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C | 1825.3 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=O)CS[Si](C)(C)C(C)(C)C | 1793.1 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C | 1883.6 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C | 1890.7 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS)O[Si](C)(C)C(C)(C)C | 1756.8 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O | 1961.7 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O | 1949.3 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=CS[Si](C)(C)C(C)(C)C)C(=O)O | 1904.8 | Standard polar | 33892256 | 3-Mercaptopyruvic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2188.3 | Semi standard non polar | 33892256 | 3-Mercaptopyruvic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 2057.9 | Standard non polar | 33892256 | 3-Mercaptopyruvic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(=CS[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 1929.4 | 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 - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9000000000-b81f8808977132c3a8ac | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9300000000-5100fd5cbb3bf9df1e75 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 3-Mercaptopyruvic acid 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-003r-9200000000-f1e0c53958ad51dc0068 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-001j-9000000000-60f6deb41f42078dd60c | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-001i-9000000000-5dc69d3b59bd15290aef | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF | splash10-02t9-9000000000-e1511333b005fa911312 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF | splash10-00kf-9000000000-65854057c742d34c8dbb | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF | splash10-006w-9000000000-66939f30bca1061b4b83 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOF | splash10-0fk9-2900000000-0da521157f8235fe7758 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOF | splash10-0fk9-7900000000-8c127be0565b54938cd2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOF | splash10-0ab9-9000000000-d4a8d07d451ba309b2e2 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF | splash10-014i-1900000000-849e74ceb9308736ba6d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF | splash10-0gb9-2900000000-5a713232367a68a966a0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF | splash10-0fk9-9300000000-564344466a63b943c6da | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Negative-QTOF | splash10-006x-9200000000-95772f7f626a811df489 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Negative-QTOF | splash10-001i-9000000000-32551e3b5faf0b1e7000 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Negative-QTOF | splash10-001i-9000000000-572c315b879edca344fa | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 10V, Positive-QTOF | splash10-00di-9400000000-8738d67598547a4b3429 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 20V, Positive-QTOF | splash10-00di-9000000000-4ba1ab7a6a1dc95bba23 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3-Mercaptopyruvic acid 40V, Positive-QTOF | splash10-0002-9000000000-6a9a04efc4b7bb2af1eb | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2012-12-04 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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