Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-02-23 10:30:31 UTC |
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Update Date | 2023-02-21 17:15:51 UTC |
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HMDB ID | HMDB0001863 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Hydroxyvaleric acid |
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Description | 2-Hydroxyvaleric acid is an organic acid present in human biofluids. Its presence in urine has been associated with lactic acidosis, which occurs in Succinic Acidemia (OMIM 600335 ), a syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. 2-Hydroxyvaleric acid presence associated with lactic acidosis has also been found in Propionyl-CoA carboxylase deficiency (OMIM 253260 ), or Multiple carboxylase deficiency (MCD), an autosomal recessive metabolic disorder characterized primarily by cutaneous and neurologic abnormalities. (PMID: 9389332 , 1790187 , 3378323 , 3383430 , 7313494 ). |
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Structure | InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8) |
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Synonyms | Value | Source |
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alpha-Hydroxy-N-valeric acid | ChEBI | alpha-Hydroxyvaleric acid | ChEBI | a-Hydroxy-N-valerate | Generator | a-Hydroxy-N-valeric acid | Generator | alpha-Hydroxy-N-valerate | Generator | Α-hydroxy-N-valerate | Generator | Α-hydroxy-N-valeric acid | Generator | a-Hydroxyvalerate | Generator | a-Hydroxyvaleric acid | Generator | alpha-Hydroxyvalerate | Generator | Α-hydroxyvalerate | Generator | Α-hydroxyvaleric acid | Generator | 2-Hydroxyvalerate | Generator | (+-)-2-Hydroxypentanoate | HMDB | (+-)-2-Hydroxypentanoic acid | HMDB | (S)-2-Hydroxyvaleric acid | HMDB | 2-Hydroxy-pentanoate | HMDB | 2-Hydroxy-pentanoic acid | HMDB | 2-Hydroxypentanoate | HMDB | 2-Hydroxypentanoic acid | HMDB | DL-2-Hydroxy valeric acid | HMDB | DL-2-Hydroxy valerate | HMDB | 2-Hydroxyvaleric acid | ChEBI |
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Chemical Formula | C5H10O3 |
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Average Molecular Weight | 118.1311 |
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Monoisotopic Molecular Weight | 118.062994186 |
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IUPAC Name | 2-hydroxypentanoic acid |
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Traditional Name | pentanoic acid, 2-hydroxy- |
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CAS Registry Number | 617-31-2 |
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SMILES | CCCC(O)C(O)=O |
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InChI Identifier | InChI=1S/C5H10O3/c1-2-3-4(6)5(7)8/h4,6H,2-3H2,1H3,(H,7,8) |
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InChI Key | JRHWHSJDIILJAT-UHFFFAOYSA-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
- Hydroxy fatty acid
- Alpha-hydroxy acid
- Hydroxy acid
- Monosaccharide
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- 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 | 34 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | 0.45 | SANGSTER (1993) |
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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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2-Hydroxyvaleric acid,1TMS,isomer #1 | CCCC(O[Si](C)(C)C)C(=O)O | 1153.6 | Semi standard non polar | 33892256 | 2-Hydroxyvaleric acid,1TMS,isomer #2 | CCCC(O)C(=O)O[Si](C)(C)C | 1075.3 | Semi standard non polar | 33892256 | 2-Hydroxyvaleric acid,2TMS,isomer #1 | CCCC(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1202.6 | Semi standard non polar | 33892256 | 2-Hydroxyvaleric acid,1TBDMS,isomer #1 | CCCC(O[Si](C)(C)C(C)(C)C)C(=O)O | 1370.4 | Semi standard non polar | 33892256 | 2-Hydroxyvaleric acid,1TBDMS,isomer #2 | CCCC(O)C(=O)O[Si](C)(C)C(C)(C)C | 1290.7 | Semi standard non polar | 33892256 | 2-Hydroxyvaleric acid,2TBDMS,isomer #1 | CCCC(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1619.3 | 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 - 2-Hydroxyvaleric acid GC-EI-TOF (Non-derivatized) | splash10-000t-1900000000-d70300be52196291976d | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - 2-Hydroxyvaleric acid GC-EI-TOF (Non-derivatized) | splash10-000t-1900000000-d70300be52196291976d | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyvaleric acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-00bc-9000000000-8ef25031872550bc4b5a | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyvaleric acid GC-MS (2 TMS) - 70eV, Positive | splash10-00g1-9520000000-c9d4fd57ae20696954b7 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Hydroxyvaleric 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 - 2-Hydroxyvaleric acid LC-ESI-QTOF , negative-QTOF | splash10-01b9-5900000000-01385a49616d72e0af48 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 10V, Positive-QTOF | splash10-0gb9-5900000000-3d71ffe5b1c985dfc9cc | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 20V, Positive-QTOF | splash10-0fdo-9200000000-659ff4c4697dba592584 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 40V, Positive-QTOF | splash10-0006-9000000000-96838793607ef6f63efe | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 10V, Negative-QTOF | splash10-014i-5900000000-a4fc27ef3911175a0401 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 20V, Negative-QTOF | splash10-00di-9200000000-59dd4da8ca2bf68da3f1 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 40V, Negative-QTOF | splash10-05fu-9000000000-bc0895fffaa6399f624b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 10V, Negative-QTOF | splash10-014j-4900000000-2614517a07efec2cf55f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 20V, Negative-QTOF | splash10-01ba-9300000000-a44dada0b4de6fdaa3d5 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 40V, Negative-QTOF | splash10-0006-9000000000-e3ae3abd89704d8b4660 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 10V, Positive-QTOF | splash10-0a4i-9100000000-97bcc465197c4cce0de9 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 20V, Positive-QTOF | splash10-0a4i-9000000000-2cfc42755749c6d13ccc | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Hydroxyvaleric acid 40V, Positive-QTOF | splash10-0006-9000000000-5b66cfecc9e0301583d4 | 2021-09-23 | 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 |
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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General References | - Verhaeghe BJ, Lefevere MF, De Leenheer AP: Solid-phase extraction with strong anion-exchange columns for selective isolation and concentration of urinary organic acids. Clin Chem. 1988 Jun;34(6):1077-83. [PubMed:3378323 ]
- Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [PubMed:7313494 ]
- Jellum E, Harboe M, Bjune G, Wold S: Interpreting complicated chromatographic patterns. J Pharm Biomed Anal. 1991;9(8):663-9. [PubMed:1790187 ]
- Kim KR, Kim JH, Jeong DH, Paek DJ, Liebich HM: Gas chromatographic profiling analysis of urinary organic acids from nonsmokers and smokers. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):1-8. [PubMed:9389332 ]
- Asano K, Miyamoto I, Matsushita T, Murakami Y, Minoura S, Wagatsuma T, Oshima M: Succinic acidemia: a new syndrome of organic acidemia associated with congenital lactic acidosis and decreased NADH-cytochrome c reductase activity. Clin Chim Acta. 1988 Apr 29;173(3):305-12. [PubMed:3383430 ]
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