Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 09:49:28 UTC |
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Update Date | 2021-09-24 09:49:28 UTC |
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HMDB ID | HMDB0304444 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | oxalosuccinate |
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Description | Oxalosuccinic acid, also known as oxalosuccinate or 1-oxopropane-1,2,3-tricarboxylate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Oxalosuccinic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxalosuccinic acid can be found in a number of food items such as japanese chestnut, poppy, wax apple, and hyssop, which makes oxalosuccinic acid a potential biomarker for the consumption of these food products. Oxalosuccinic acid exists in all living species, ranging from bacteria to humans. Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. It's an alpha-keto compound, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Oxalosuccinate never leaves the active site of the enzyme, however; it's unstable and immediately undergoes decarboxylation to produce the 5-carbon compound, alpha-ketoglutarate . |
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Structure | OC(=O)CC(C(O)=O)C(=O)C(O)=O InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13) |
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Synonyms | Value | Source |
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1-Oxopropane-1,2,3-tricarboxylate | ChEBI | Oxalbernsteinsaeure | ChEBI | Oxalosuccinate | ChEBI | 1-Oxopropane-1,2,3-tricarboxylic acid | Generator | Oxalosuccinic acid | KEGG |
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Chemical Formula | C6H6O7 |
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Average Molecular Weight | 190.1076 |
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Monoisotopic Molecular Weight | 190.011352546 |
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IUPAC Name | 1-oxopropane-1,2,3-tricarboxylic acid |
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Traditional Name | oxalosuccinate |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)CC(C(O)=O)C(=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H6O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2H,1H2,(H,7,8)(H,10,11)(H,12,13) |
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InChI Key | UFSCUAXLTRFIDC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Tricarboxylic acids and derivatives |
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Direct Parent | Tricarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - Tricarboxylic acid or derivatives
- Gamma-keto acid
- Beta-keto acid
- Alpha-keto acid
- Beta-hydroxy ketone
- Keto acid
- 1,3-dicarbonyl compound
- Alpha-hydroxy ketone
- Ketone
- Carboxylic acid
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxygen compound
- 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 | 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 IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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oxalosuccinate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1873.5 | Semi standard non polar | 33892256 | oxalosuccinate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1836.4 | Standard non polar | 33892256 | oxalosuccinate,4TMS,isomer #1 | C[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1912.0 | Standard polar | 33892256 | oxalosuccinate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2680.9 | Semi standard non polar | 33892256 | oxalosuccinate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2600.1 | Standard non polar | 33892256 | oxalosuccinate,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)CC(C(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2475.8 | 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 - oxalosuccinate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-6900000000-05e6953cf97abc6dd674 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - oxalosuccinate GC-MS (3 TMS) - 70eV, Positive | splash10-00rf-9137000000-9567484c80debff89c0e | 2017-10-06 | 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 - oxalosuccinate 10V, Positive-QTOF | splash10-00dj-1900000000-ed9f625da4af156fd85a | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 20V, Positive-QTOF | splash10-006t-8900000000-b245ec6d4dca3949083d | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 40V, Positive-QTOF | splash10-006t-9300000000-00b8a65afa1e83c61b5a | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 10V, Negative-QTOF | splash10-000b-0900000000-a6734cca6590d164a554 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 20V, Negative-QTOF | splash10-0002-3900000000-c30d22d22f12460fcc5c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 40V, Negative-QTOF | splash10-00dj-9300000000-a3b40df9f3852aa0e3c8 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 10V, Positive-QTOF | splash10-0fi0-0900000000-de098f1139c0f6fbd19d | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 20V, Positive-QTOF | splash10-0092-9800000000-03bc5902024a449a2d18 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 40V, Positive-QTOF | splash10-00di-9000000000-ef352a8e83bf22a4b124 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 10V, Negative-QTOF | splash10-0f6t-3900000000-654a5517d3a1a65425e3 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 20V, Negative-QTOF | splash10-0f6t-7900000000-7b0190686602c20ebac6 | 2021-10-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - oxalosuccinate 40V, Negative-QTOF | splash10-0fk9-9500000000-e5f05497c77c1ef44cf0 | 2021-10-21 | 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, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | 2022-08-20 | Wishart Lab | View Spectrum |
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