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 | 2023-02-21 17:15:00 UTC |
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HMDB ID | HMDB0000624 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | D-Leucic acid |
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Description | D-Leucic acid is an alpha-hydroxycarboxylic acid present in patients affected with Short-bowel syndrome (an Inborn errors of metabolism, OMIM 175200 ) (PMID 9766851 ), and in Maple Syrup Urine Disease (MSUD, an autosomal recessive inherited metabolic disorder of branched-chain amino acid) (PMID 9766851 ). |
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Structure | InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1 |
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Synonyms | Value | Source |
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(R)-2-Hydroxy-4-methylvaleric acid | ChEBI | (R)-2-Hydroxyisocaproic acid | ChEBI | (R)-Leucic acid | ChEBI | 2-Hydroxy-4-methyl-D-valeric acid | ChEBI | alpha-Hydroxyisocaproic acid | ChEBI | D-2-Hydroxy-4-methylpentanoic acid | ChEBI | D-2-Hydroxy-4-methylvaleric acid | ChEBI | D-2-Hydroxyisocaproic acid | ChEBI | delta-Leucic acid | ChEBI | Leucic acid | ChEBI | D-2-Hydroxyisocaproate | Kegg | (R)-2-Hydroxy-4-methylpentanoate | Kegg | D-Leucate | Kegg | (R)-2-Hydroxy-4-methylvalerate | Generator | (R)-2-Hydroxyisocaproate | Generator | (R)-Leucate | Generator | 2-Hydroxy-4-methyl-D-valerate | Generator | a-Hydroxyisocaproate | Generator | a-Hydroxyisocaproic acid | Generator | alpha-Hydroxyisocaproate | Generator | Α-hydroxyisocaproate | Generator | Α-hydroxyisocaproic acid | Generator | D-2-Hydroxy-4-methylpentanoate | Generator | D-2-Hydroxy-4-methylvalerate | Generator | delta-Leucate | Generator | Δ-leucate | Generator | Δ-leucic acid | Generator | Leucate | Generator | (R)-2-Hydroxy-4-methylpentanoic acid | Generator | (-)-2-Hydroxyisocaproate | HMDB | (-)-2-Hydroxyisocaproic acid | HMDB | (-)-a-Hydroxyisocaproate | HMDB | (-)-a-Hydroxyisocaproic acid | HMDB | (-)-alpha-Hydroxyisocaproate | HMDB | (-)-alpha-Hydroxyisocaproic acid | HMDB | (R)-2-Hydroxy-4-methyl-pentanoate | HMDB | (R)-2-Hydroxy-4-methyl-pentanoic acid | HMDB | 2-Hydroxy-4-methyl-delta-valerate | HMDB | 2-Hydroxy-4-methyl-delta-valeric acid | HMDB | D-a-Hydroxyisocaproate | HMDB | D-a-Hydroxyisocaproic acid | HMDB | delta-2-Hydroxy-4-methylpentanoate | HMDB | delta-2-Hydroxy-4-methylpentanoic acid | HMDB | delta-2-Hydroxy-4-methylvalerate | HMDB | delta-2-Hydroxy-4-methylvaleric acid | HMDB | delta-2-Hydroxyisocaproate | HMDB | delta-2-Hydroxyisocaproic acid | HMDB | delta-alpha-Hydroxyisocaproate | HMDB | delta-alpha-Hydroxyisocaproic acid | HMDB |
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Chemical Formula | C6H12O3 |
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Average Molecular Weight | 132.1577 |
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Monoisotopic Molecular Weight | 132.07864425 |
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IUPAC Name | (2R)-2-hydroxy-4-methylpentanoic acid |
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Traditional Name | (-)-α-hydroxyisocaproate |
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CAS Registry Number | 20312-37-2 |
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SMILES | CC(C)C[C@@H](O)C(O)=O |
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InChI Identifier | InChI=1S/C6H12O3/c1-4(2)3-5(7)6(8)9/h4-5,7H,3H2,1-2H3,(H,8,9)/t5-/m1/s1 |
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InChI Key | LVRFTAZAXQPQHI-RXMQYKEDSA-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
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Alpha-hydroxy acid
- Hydroxy acid
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Carbonyl group
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen 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 | |
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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-Leucic acid,1TMS,isomer #1 | CC(C)C[C@@H](O[Si](C)(C)C)C(=O)O | 1189.3 | Semi standard non polar | 33892256 | D-Leucic acid,1TMS,isomer #2 | CC(C)C[C@@H](O)C(=O)O[Si](C)(C)C | 1121.8 | Semi standard non polar | 33892256 | D-Leucic acid,2TMS,isomer #1 | CC(C)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1237.3 | Semi standard non polar | 33892256 | D-Leucic acid,1TBDMS,isomer #1 | CC(C)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O | 1404.6 | Semi standard non polar | 33892256 | D-Leucic acid,1TBDMS,isomer #2 | CC(C)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C | 1356.0 | Semi standard non polar | 33892256 | D-Leucic acid,2TBDMS,isomer #1 | CC(C)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 1676.3 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-866999574fff80fabad1 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (2 TMS) - 70eV, Positive | splash10-02gc-9440000000-7fffd162011678b17f4a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic acid GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - D-Leucic 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 - D-Leucic acid LC-ESI-QQ , negative-QTOF | splash10-001i-0900000000-74d5e5f39ea37f777aca | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOF | splash10-0019-9500000000-7c7c7dc2d6548a20789d | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOF | splash10-00kr-9000000000-226ab1053ca4714d6bc1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOF | splash10-014i-9000000000-027f1c6ebbf703c13661 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - D-Leucic acid LC-ESI-QQ , negative-QTOF | splash10-014i-9000000000-6217c9555a8c971b5dee | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 10V, Positive-QTOF | splash10-0159-5900000000-01e9c211c49cea6fc5c6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 20V, Positive-QTOF | splash10-0ap0-9300000000-a1f6fc289aa530d63fd8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 40V, Positive-QTOF | splash10-0a4i-9000000000-eb5a5d102c8e756f6834 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 10V, Negative-QTOF | splash10-001i-2900000000-1a66b9767516fbd45630 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 20V, Negative-QTOF | splash10-06s9-9400000000-cf71f1c20e2a87bbb2b0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 40V, Negative-QTOF | splash10-0a4i-9000000000-11e049c8df5b1a6268c9 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 10V, Negative-QTOF | splash10-0019-9700000000-a7d0b1ce1c211b31bc0d | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 20V, Negative-QTOF | splash10-00kr-9100000000-504826b66e199a65ef09 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 40V, Negative-QTOF | splash10-014l-9000000000-ccecb4a470c359949fec | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 10V, Positive-QTOF | splash10-014i-9000000000-3019a9d0620e7da01963 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 20V, Positive-QTOF | splash10-00kf-9000000000-e587d44396e53f2409fa | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - D-Leucic acid 40V, Positive-QTOF | splash10-0006-9000000000-457ece1d510dad645c89 | 2021-09-24 | 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) | 2021-09-16 | 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 |
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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