Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2022-09-22 18:34:14 UTC |
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HMDB ID | HMDB0000749 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Mesaconic acid |
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Description | Mesaconic acid, also known as 2-methylfumarate or citronic acid, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Mesaconic acid is a dicarboxylic butenoic acid, with a methyl group in position 2 and the double bound between carbons 2 and 3. Mesaconic acid was first studied for its physical properties in 1874 by Jacobus van ‘t Hoff (https://web.archive.org/web/20051117102410/http://dbhs.wvusd.k12.ca.us/webdocs/Chem-History/Van%27t-Hoff-1874.html). It is now known to be involved in the biosynthesis of vitamin B12 and it is also a competitor inhibitor of the reduction of fumarate. |
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Structure | InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ |
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Synonyms | Value | Source |
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(e)-2-Methyl-2-butenedioic acid | ChEBI | (e)-Citraconic acid | ChEBI | 2-Methylfumaric acid | ChEBI | Citronic acid | ChEBI | Methylfumaric acid | ChEBI | trans-1-Propene-1,2-dicarboxylic acid | ChEBI | trans-2-Methyl-2-butenedioic acid | ChEBI | 2-Methylfumarate | Kegg | (e)-2-Methyl-2-butenedioate | Generator | (e)-Citraconate | Generator | Citronate | Generator | Methylfumarate | Generator | trans-1-Propene-1,2-dicarboxylate | Generator | trans-2-Methyl-2-butenedioate | Generator | Mesaconate | Generator | (Z)-2-Methyl-2-butenedioic acid | HMDB | Citraconic acid | HMDB | Citraconic acid, (e)-isomer | HMDB | Citraconic acid, ammonium salt | HMDB | Citraconic acid, calcium salt | HMDB | Citraconic acid, sodium salt | HMDB | Methylmaleic acid | HMDB | Monomethylfumarate | HMDB | (2E)-2-Methyl-2-butenedioate | HMDB | (2E)-2-Methyl-2-butenedioic acid | HMDB |
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Chemical Formula | C5H6O4 |
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Average Molecular Weight | 130.0987 |
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Monoisotopic Molecular Weight | 130.02660868 |
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IUPAC Name | (2E)-2-methylbut-2-enedioic acid |
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Traditional Name | mesaconic acid |
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CAS Registry Number | 498-24-8 |
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SMILES | C\C(=C/C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+ |
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InChI Key | HNEGQIOMVPPMNR-NSCUHMNNSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty acids and conjugates |
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Direct Parent | Methyl-branched fatty acids |
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Alternative Parents | |
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Substituents | - Methyl-branched fatty acid
- Unsaturated fatty acid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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 | 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 | Solid |
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Experimental Molecular Properties | |
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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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Mesaconic acid,1TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C(=O)O | 1324.8 | Semi standard non polar | 33892256 | Mesaconic acid,1TMS,isomer #2 | C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C | 1326.7 | Semi standard non polar | 33892256 | Mesaconic acid,2TMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1388.2 | Semi standard non polar | 33892256 | Mesaconic acid,1TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O | 1567.9 | Semi standard non polar | 33892256 | Mesaconic acid,1TBDMS,isomer #2 | C/C(=C\C(=O)O)C(=O)O[Si](C)(C)C(C)(C)C | 1567.1 | Semi standard non polar | 33892256 | Mesaconic acid,2TBDMS,isomer #1 | C/C(=C\C(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1802.1 | Semi standard non polar | 33892256 |
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Spectra |
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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 - Mesaconic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-0002-1910000000-7b5cb889d8459c0edd01 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesaconic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS) | splash10-00di-9500000000-b21cd4d2b489173d2933 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesaconic acid GC-MS (2 TMS) | splash10-053r-2940000000-4329a46b213ac4abcca9 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesaconic acid GC-EI-TOF (Non-derivatized) | splash10-0002-1910000000-7b5cb889d8459c0edd01 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesaconic acid GC-EI-TOF (Non-derivatized) | splash10-00di-9500000000-b21cd4d2b489173d2933 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) | splash10-053r-2940000000-4329a46b213ac4abcca9 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-01q3-9200000000-99f5b89fc0026d764b2b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (2 TMS) - 70eV, Positive | splash10-05g3-9540000000-ba938fe63ed9356955c6 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Mesaconic acid GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-11-05 | 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 - Mesaconic acid Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-000j-9400000000-e10edb30d7748a7adb05 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Mesaconic acid Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-00m0-9000000000-6ef60fd2abfbb5741bca | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Mesaconic acid Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0159-9000000000-e14ffb74e5a8298232a3 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Mesaconic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-000i-9100000000-8749d95b95760456aeed | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Mesaconic acid LC-ESI-QTOF , negative-QTOF | splash10-000i-9100000000-8749d95b95760456aeed | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 10V, Positive-QTOF | splash10-03di-5900000000-48835a534a81752d3085 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 20V, Positive-QTOF | splash10-00kr-9100000000-dcbf0f65cbb6f9b6b578 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 40V, Positive-QTOF | splash10-000i-9000000000-632723c704c4db90a4b6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 10V, Negative-QTOF | splash10-004r-5900000000-4b2260c72d18030ec912 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 20V, Negative-QTOF | splash10-002r-9500000000-1fd59395c864782b12b9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 40V, Negative-QTOF | splash10-014u-9000000000-b6d65140f365dabf3b3a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 10V, Positive-QTOF | splash10-01p9-9400000000-ebf4634a042628bb8a44 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 20V, Positive-QTOF | splash10-00ko-9000000000-e04449c635203c9d3da0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 40V, Positive-QTOF | splash10-0006-9000000000-1b2c407328e3780e996e | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 10V, Negative-QTOF | splash10-000i-9000000000-ec20127c74818b1f634d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 20V, Negative-QTOF | splash10-000i-9000000000-8867d7b163c801abd185 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Mesaconic acid 40V, Negative-QTOF | splash10-014l-9000000000-55fcd5974652df621054 | 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, 600 MHz, H2O, experimental) | 2021-10-10 | 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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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane
- Mitochondria
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Cancer patients undergoing total body irradiation | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022221 |
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KNApSAcK ID | C00051539 |
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Chemspider ID | 10289044 |
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KEGG Compound ID | C01732 |
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BioCyc ID | Not Available |
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BiGG ID | 38272 |
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Wikipedia Link | Mesaconic_acid |
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METLIN ID | 4130 |
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PubChem Compound | 638129 |
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PDB ID | MEZ |
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ChEBI ID | 16600 |
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Food Biomarker Ontology | Not Available |
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VMH ID | MESCON |
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MarkerDB ID | Not Available |
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Good Scents ID | rw1257141 |
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References |
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Synthesis Reference | Shriner, R. L.; Ford, S. G.; Roll, L. J. Mesaconic acid. Organic Syntheses (1931), XI 74-5. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]
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