Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2012-09-11 20:10:47 UTC |
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Update Date | 2023-02-21 17:24:42 UTC |
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HMDB ID | HMDB0035227 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Hydroxypropanedioic acid |
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Description | Hydroxypropanedioic acid, also known as 2-tartronic acid or 2-hydroxymalonate, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Hydroxypropanedioic acid has been detected, but not quantified in, potatos (Solanum tuberosum). This could make hydroxypropanedioic acid a potential biomarker for the consumption of these foods. Hydroxypropanedioic 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 Hydroxypropanedioic acid. |
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Structure | InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8) |
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Synonyms | Value | Source |
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2-Hydroxymalonate | ChEBI | 2-Hydroxymalonic acid | ChEBI | 2-Hydroxypropanedioic acid | ChEBI | 2-Tartronic acid | ChEBI | Tartronic acid | ChEBI | Hydroxymalonic acid | Kegg | 2-Hydroxypropanedioate | Generator | 2-Tartronate | Generator | Tartronate | Generator | Hydroxymalonate | Generator | Hydroxypropanedioate | Generator | Hydroxy-malonic acid | HMDB | Propanedioic acid, hydroxy- (9ci) | HMDB | Tartronic acid, 8ci | HMDB |
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Chemical Formula | C3H4O5 |
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Average Molecular Weight | 120.0609 |
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Monoisotopic Molecular Weight | 120.005873238 |
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IUPAC Name | 2-hydroxypropanedioic acid |
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Traditional Name | tartronic acid |
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CAS Registry Number | 80-69-3 |
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SMILES | OC(C(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C3H4O5/c4-1(2(5)6)3(7)8/h1,4H,(H,5,6)(H,7,8) |
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InChI Key | ROBFUDYVXSDBQM-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid 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 | Dicarboxylic acids and derivatives |
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Direct Parent | Dicarboxylic acids and derivatives |
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Alternative Parents | |
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Substituents | - 1,3-dicarbonyl compound
- Monosaccharide
- Hydroxy acid
- Dicarboxylic acid or derivatives
- 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 | |
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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 | 156 - 158 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000000 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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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Hydroxypropanedioic acid,1TMS,isomer #1 | C[Si](C)(C)OC(C(=O)O)C(=O)O | 1295.5 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,1TMS,isomer #2 | C[Si](C)(C)OC(=O)C(O)C(=O)O | 1193.9 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,2TMS,isomer #1 | C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(=O)O | 1315.6 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,2TMS,isomer #2 | C[Si](C)(C)OC(=O)C(O)C(=O)O[Si](C)(C)C | 1275.9 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,3TMS,isomer #1 | C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1412.8 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(C(=O)O)C(=O)O | 1560.8 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(O)C(=O)O | 1452.2 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(=O)O | 1755.2 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)C(O)C(=O)O[Si](C)(C)C(C)(C)C | 1718.0 | Semi standard non polar | 33892256 | Hydroxypropanedioic acid,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1993.6 | 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 - Hydroxypropanedioic acid GC-MS (3 TMS) | splash10-0ue9-0930000000-72836d646b8c3440486d | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (4 TMS) | splash10-008c-1983000000-a595fea5038ab6a983d2 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (Non-derivatized) | splash10-0ue9-0930000000-72836d646b8c3440486d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (Non-derivatized) | splash10-008c-1983000000-a595fea5038ab6a983d2 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Hydroxypropanedioic acid GC-EI-TOF (Non-derivatized) | splash10-0f7k-0910000000-3c772d60bdd00371bb5d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fml-9300000000-ce47a47fbac5b3203273 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (3 TMS) - 70eV, Positive | splash10-00xr-9161000000-97e3c100b5034fcc3bdc | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Hydroxypropanedioic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-057i-9000000000-8869f8e57dc896c8634b | 2015-03-01 | Not Available | 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 - Hydroxypropanedioic acid LC-ESI-QQ , negative-QTOF | splash10-066r-8900000000-16ebb5f175ac6ca39ab2 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxypropanedioic acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-3b2f9b0a130dd49117a1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxypropanedioic acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-3af4b557f3ccb85e572e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxypropanedioic acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-0e67c1f979c08e6c1324 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Hydroxypropanedioic acid LC-ESI-QQ , negative-QTOF | splash10-0a4i-9000000000-c80ff83bde053c84f6d6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 10V, Positive-QTOF | splash10-0fk9-1900000000-eacff3e7b8c5b7a4bb46 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 20V, Positive-QTOF | splash10-0umi-5900000000-43842f30c6f53f622e3c | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 40V, Positive-QTOF | splash10-0a4i-9200000000-5cba6b9d751d47649575 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 10V, Negative-QTOF | splash10-016r-7900000000-0b7d28cdb82196bf0fcf | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 20V, Negative-QTOF | splash10-0gk9-9700000000-c950dc2924a2c4743ce6 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 40V, Negative-QTOF | splash10-0adi-9000000000-6aa558d0b6aa291cb54f | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 10V, Negative-QTOF | splash10-004i-9000000000-83447deaed87d4a00289 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 20V, Negative-QTOF | splash10-004i-9000000000-ab5564fb2ec1e5141afe | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 40V, Negative-QTOF | splash10-004i-9000000000-1a88c467a4b5c7d88e2e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 10V, Positive-QTOF | splash10-0udi-8900000000-f45a1b9f46cbcf26da3e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 20V, Positive-QTOF | splash10-0kec-9100000000-fe863012da4888754a35 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Hydroxypropanedioic acid 40V, Positive-QTOF | splash10-052f-9000000000-55e53a0542d2efef6013 | 2021-09-22 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | 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+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 | - Guerranti R, Pagani R, Neri S, Errico SV, Leoncini R, Marinello E: Inhibition and regulation of rat liver L-threonine dehydrogenase by different fatty acids and their derivatives. Biochim Biophys Acta. 2001 Nov 7;1568(1):45-52. [PubMed:11731084 ]
- Jacob J, Grimmer G: [Occurrence of alkyl-hydroxymalonic acids in uropygial gland secretions of birds (author's transl)]. Hoppe Seylers Z Physiol Chem. 1973 Dec;354(12):1648-50. [PubMed:4803853 ]
- VEITCH FP, BRIERLEY GP: The quantitative determination of tartronic acid (hydroxymalonic acid) in urine and tissues. Biochim Biophys Acta. 1962 Apr 23;58:567-73. [PubMed:14039995 ]
- Knope KE, Kimura H, Yasaka Y, Nakahara M, Andrews MB, Cahill CL: Investigation of in situ oxalate formation from 2,3-pyrazinedicarboxylate under hydrothermal conditions using nuclear magnetic resonance spectroscopy. Inorg Chem. 2012 Mar 19;51(6):3883-90. doi: 10.1021/ic3000944. Epub 2012 Feb 24. [PubMed:22360688 ]
- Shen JM, Chen ZL, Xu ZZ, Li XY, Xu BB, Qi F: Kinetics and mechanism of degradation of p-chloronitrobenzene in water by ozonation. J Hazard Mater. 2008 Apr 15;152(3):1325-31. Epub 2007 Aug 8. [PubMed:17889996 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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