Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:19:53 UTC |
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Update Date | 2023-02-21 17:17:39 UTC |
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HMDB ID | HMDB0012140 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (R)-2,3-Dihydroxy-3-methylvalerate |
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Description | (R)-2,3-Dihydroxy-methylvalerate is an intermediate in valine, leucine, and isoleucine biosynthesis. The pathway of valine biosynthesis is a four-step pathway that shares all of its steps with the parallel pathway of isoleucine biosynthesis. These entwined pathways are part of the superpathway of leucine, valine, and isoleucine biosynthesis, which generates not only isoleucine and valine but also leucine. (R)-2,3-Dihydroxy-methylvalerate is generated from 3-hydroxy-3-methyl-2-oxopentanoic acid via the enzyme ketol-acid reductoisomerase (EC 1.1.1.86). It is converted into (S)-3-methyl-2-oxopentanoic via the dihydroxy-acid dehydratase (EC 4.2.1.9). |
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Structure | CC[C@@](C)(O)[C@@H](O)C(O)=O InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1 |
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Synonyms | Value | Source |
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(2R,3R)-2,3-Dihydroxy-3-methylvaleric acid | ChEBI | (2R,3R)-2,3-Dihydroxy-3-methylpentanoate | Kegg | (2R,3R)-2,3-Dihydroxy-3-methylvalerate | Generator | (2R,3R)-2,3-Dihydroxy-3-methylpentanoic acid | Generator | (R)-2,3-Dihydroxy-3-methylvaleric acid | Generator | (R) 2,3-Dihydroxy-3-methylvaleric acid | Generator, HMDB | (R)-2,3-Dihydroxy-3-methylpentanoate | HMDB | (R)-2,3-Dihydroxy-3-methylpentanoic acid | HMDB | (R)-2,3-Dihydroxy-3-methylvalerate | HMDB, KEGG | 1-keto-2-Methylvalerate | HMDB | 2,3-Dihydroxy-3-methyl-valeric acid | HMDB | 2,3-Dihydroxy-3-methylpentanoate | HMDB | 2,3-Dihydroxy-3-methylpentanoic acid | HMDB | 2,3-Dihydroxy-valerianic acid | HMDB | 4,5-Dideoxy-3-C-methyl-pentonic acid | HMDB | alpha,beta-Dihydroxy-beta-methylvaleric acid | HMDB | CID8 | HMDB | DMV | HMDB |
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Chemical Formula | C6H12O4 |
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Average Molecular Weight | 148.1571 |
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Monoisotopic Molecular Weight | 148.073558872 |
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IUPAC Name | (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid |
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Traditional Name | (2R,3R)-2,3-dihydroxy-3-methylpentanoic acid |
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CAS Registry Number | 562-43-6 |
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SMILES | CC[C@@](C)(O)[C@@H](O)C(O)=O |
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InChI Identifier | InChI=1S/C6H12O4/c1-3-6(2,10)4(7)5(8)9/h4,7,10H,3H2,1-2H3,(H,8,9)/t4-,6+/m0/s1 |
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InChI Key | PDGXJDXVGMHUIR-UJURSFKZSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group. |
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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 | Hydroxy fatty acids |
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Alternative Parents | |
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Substituents | - Branched fatty acid
- Methyl-branched fatty acid
- Short-chain hydroxy acid
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Hydroxy acid
- Monosaccharide
- Tertiary alcohol
- 1,2-diol
- Secondary alcohol
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Organooxygen 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 | |
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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 | 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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(R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #1 | CC[C@@](C)(O[Si](C)(C)C)[C@@H](O)C(=O)O | 1346.4 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #2 | CC[C@@](C)(O)[C@@H](O[Si](C)(C)C)C(=O)O | 1320.4 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,1TMS,isomer #3 | CC[C@@](C)(O)[C@@H](O)C(=O)O[Si](C)(C)C | 1246.6 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #1 | CC[C@@](C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O | 1421.4 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #2 | CC[C@@](C)(O[Si](C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C | 1382.9 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TMS,isomer #3 | CC[C@@](C)(O)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1324.9 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,3TMS,isomer #1 | CC[C@@](C)(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1458.7 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #1 | CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O | 1600.4 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #2 | CC[C@@](C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 1562.3 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,1TBDMS,isomer #3 | CC[C@@](C)(O)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 1482.8 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #1 | CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 1863.2 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #2 | CC[C@@](C)(O[Si](C)(C)C(C)(C)C)[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 1827.9 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,2TBDMS,isomer #3 | CC[C@@](C)(O)[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1805.4 | Semi standard non polar | 33892256 | (R)-2,3-Dihydroxy-3-methylvalerate,3TBDMS,isomer #1 | CC[C@@](C)(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 | 2102.2 | Semi standard non 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 - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9000000000-d382043e81321879e92e | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (3 TMS) - 70eV, Positive | splash10-00tb-9464000000-0280de9eaa4c12333997 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Positive-QTOF | splash10-05aj-7900000000-ed4255c918254a1dc462 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Positive-QTOF | splash10-0kar-9600000000-420faa83ea76001db2e9 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Positive-QTOF | splash10-0pb9-9000000000-393b15b5811231e32693 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Negative-QTOF | splash10-0udj-2900000000-d582074beb8b89338fa5 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Negative-QTOF | splash10-00di-9400000000-5ee3e425ebda8358d337 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Negative-QTOF | splash10-05g0-9000000000-db72ead6bd87a129b325 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Positive-QTOF | splash10-0h32-2900000000-0dc4c2a3c02313bed77c | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Positive-QTOF | splash10-0a4i-9000000000-431db2e8dea59bdd5c38 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Positive-QTOF | splash10-0a4i-9000000000-349f8877717c1418480e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 10V, Negative-QTOF | splash10-0002-0900000000-81689c0553421abfcd88 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 20V, Negative-QTOF | splash10-004i-9100000000-d9815468ea9acf930e9e | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-2,3-Dihydroxy-3-methylvalerate 40V, Negative-QTOF | splash10-052f-9100000000-f894bf4ab44aaac79501 | 2021-09-25 | 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, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-) | 2022-02-11 | 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+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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