Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-02-23 12:38:32 UTC |
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Update Date | 2023-02-21 17:15:53 UTC |
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HMDB ID | HMDB0001874 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-threo-Isocitric acid |
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Description | D-threo-Isocitric acid, also known as isocitrate or isocitrIC ACID, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. D-threo-Isocitric acid exists in all living species, ranging from bacteria to plants to humans. D-threo-Isocitric acid has been detected, but not quantified in, several different foods, such as salmonberries (Rubus spectabilis), black elderberries (Sambucus nigra), common peas (Pisum sativum), nectarines (Prunus persica var. nucipersica), and olives (Olea europaea). This could make D-threo-isocitric acid a potential biomarker for the consumption of these foods. D-threo-Isocitric acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on D-threo-Isocitric acid. |
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Structure | O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4+/m0/s1 |
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Synonyms | Value | Source |
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(+)-Threo-isocitric acid | ChEBI | ISOCITRIC ACID | ChEBI | (+)-Threo-isocitrate | Generator | ISOCITRate | Generator | D-Threo-isocitrate | Generator | (1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylate | HMDB | (1R,2S)-1-Hydroxypropane-1,2,3-tricarboxylic acid | HMDB | (2R,3S)-Isocitrate | HMDB | 3-Carboxy-2,3-dideoxy-L-threo-pentaric acid | HMDB | D-(+)-threo-Isocitric acid(2R,3S)-isocitric acid | HMDB | DS-threo-Isocitrate | HMDB | DS-threo-Isocitric acid | HMDB | ICI | HMDB | ICT | HMDB | threo-D-(+)-Isocitrate | HMDB | threo-D-(+)-Isocitric acid | HMDB | threo-DS(+)-Isocitrate | HMDB | threo-DS(+)-Isocitric acid | HMDB | threo-Isocitrate | HMDB | Isocitric acid, trisodium salt | MeSH, HMDB | Isocitric acid, (11)C-labeled | MeSH, HMDB | Isocitric acid, disodium salt | MeSH, HMDB | Isocitric acid, calcium salt | MeSH, HMDB | Isocitric acid, potassium salt | MeSH, HMDB | Isocitric acid, sodium salt | MeSH, HMDB |
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Chemical Formula | C6H8O7 |
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Average Molecular Weight | 192.1235 |
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Monoisotopic Molecular Weight | 192.02700261 |
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IUPAC Name | (1R,2S)-1-hydroxypropane-1,2,3-tricarboxylic acid |
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Traditional Name | threo-DS(+)-isocitrate |
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CAS Registry Number | 6061-97-8 |
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SMILES | O[C@H]([C@H](CC(O)=O)C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4+/m0/s1 |
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InChI Key | ODBLHEXUDAPZAU-ZAFYKAAXSA-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
- Beta-hydroxy acid
- Monosaccharide
- Hydroxy acid
- Alpha-hydroxy acid
- Secondary alcohol
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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 | |
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Role | Not Available |
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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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D-threo-Isocitric acid,1TMS,isomer #1 | C[Si](C)(C)O[C@@H](C(=O)O)[C@H](CC(=O)O)C(=O)O | 1641.8 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O)C(=O)O | 1646.8 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O)C(=O)O | 1629.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TMS,isomer #4 | C[Si](C)(C)OC(=O)[C@H](O)[C@H](CC(=O)O)C(=O)O | 1640.3 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C)[C@H](CC(=O)O)C(=O)O | 1694.8 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O | 1709.3 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O | 1698.4 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #4 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)C(=O)O | 1706.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #5 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C | 1695.0 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TMS,isomer #6 | C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C | 1693.4 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1765.6 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1773.4 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TMS,isomer #3 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O | 1770.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TMS,isomer #4 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C | 1783.6 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,4TMS,isomer #1 | C[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1880.1 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H](C(=O)O)[C@H](CC(=O)O)C(=O)O | 1907.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O)C(=O)O | 1926.2 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O)C(=O)O | 1904.2 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)[C@H](CC(=O)O)C(=O)O | 1913.2 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CC(=O)O)C(=O)O | 2144.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 2162.7 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 2153.8 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O | 2156.3 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 2161.1 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 2152.4 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2426.0 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2421.2 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 2448.8 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 2422.5 | Semi standard non polar | 33892256 | D-threo-Isocitric acid,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2646.9 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - D-threo-Isocitric acid GC-EI-TOF (Non-derivatized) | splash10-0002-0952000000-aeb4dfa5b7b1d6eba92f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-threo-Isocitric acid GC-EI-TOF (Non-derivatized) | splash10-0002-1920000000-b56fdff61401e2340d50 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-threo-Isocitric acid GC-EI-TOF (Non-derivatized) | splash10-0002-0952000000-aeb4dfa5b7b1d6eba92f | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - D-threo-Isocitric acid GC-EI-TOF (Non-derivatized) | splash10-0002-1920000000-b56fdff61401e2340d50 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-threo-Isocitric acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00ba-7900000000-96194d87d52b155cf1b9 | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-threo-Isocitric acid GC-MS (4 TMS) - 70eV, Positive | splash10-02vi-7029500000-2bb65fc897e48cc21750 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-threo-Isocitric acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-threo-Isocitric 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 - D-threo-Isocitric acid Quattro_QQQ 10V, Negative-QTOF (Annotated) | splash10-0udi-0900000000-24949c0952ed64de7083 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-threo-Isocitric acid Quattro_QQQ 25V, Negative-QTOF (Annotated) | splash10-0w29-1900000000-c9bdca817d12cb4b091b | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-threo-Isocitric acid Quattro_QQQ 40V, Negative-QTOF (Annotated) | splash10-014l-9300000000-66e9d659711c1d339f76 | 2012-07-24 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 10V, Positive-QTOF | splash10-004j-0900000000-a75a4b486df1552d6d93 | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 20V, Positive-QTOF | splash10-0gla-4900000000-d04fec4218cafd6195df | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 40V, Positive-QTOF | splash10-0fk9-8900000000-4e5fbbb415df9fbc8f31 | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 10V, Negative-QTOF | splash10-00ke-1900000000-c364bae4640e201c366d | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 20V, Negative-QTOF | splash10-0v4j-4900000000-d00f263a75673b7981c7 | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 40V, Negative-QTOF | splash10-0pk9-9200000000-156693398229f972d717 | 2016-09-14 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 10V, Positive-QTOF | splash10-056r-0900000000-4e17b6a1e2aad4076c03 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 20V, Positive-QTOF | splash10-0ufr-1900000000-15b65374b78661650dfa | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 40V, Positive-QTOF | splash10-00di-9100000000-f126784f2170bc8d341a | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 10V, Negative-QTOF | splash10-002f-1900000000-33d42ec37993dc647513 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 20V, Negative-QTOF | splash10-0ufr-4900000000-7b0e1ae548050695b9d6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-threo-Isocitric acid 40V, Negative-QTOF | splash10-0ufu-9600000000-3667240157dc2ec377ae | 2021-09-24 | 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 | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-16 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | 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]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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