Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2016-10-26 22:09:14 UTC |
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Update Date | 2023-02-21 17:30:39 UTC |
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HMDB ID | HMDB0062180 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Lactoylisoleucine |
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Description | N-Lactoylisoleucine is a lactoyl derivative of phenylalanine. N-Lactoyl-amino acids are ubiquitous pseudodipeptides of lactic acid and amino acids that are rapidly formed by reverse proteolysis. A protease, cytosolic nonspecific dipeptidase 2 (CNDP2), catalyzes their formation. The plasma levels of these metabolites strongly correlate with plasma levels of lactate and amino acid (PMID: 25964343 ). |
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Structure | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O)C(O)=O InChI=1S/C10H18O4/c1-4-6(2)8(10(13)14)5-9(12)7(3)11/h6-8,11H,4-5H2,1-3H3,(H,13,14)/t6-,7+,8+/m1/s1 |
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Synonyms | Value | Source |
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(2S,5S)-2-[(2R)-Butan-2-yl]-5-hydroxy-4-oxohexanoate | Generator | N-Lactoyl-isoleucine | HMDB |
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Chemical Formula | C10H18O4 |
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Average Molecular Weight | 202.25 |
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Monoisotopic Molecular Weight | 202.12050906 |
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IUPAC Name | (2S,5S)-2-[(2R)-butan-2-yl]-5-hydroxy-4-oxohexanoic acid |
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Traditional Name | (2S,5S)-2-[(2R)-butan-2-yl]-5-hydroxy-4-oxohexanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O)C(O)=O |
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InChI Identifier | InChI=1S/C10H18O4/c1-4-6(2)8(10(13)14)5-9(12)7(3)11/h6-8,11H,4-5H2,1-3H3,(H,13,14)/t6-,7+,8+/m1/s1 |
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InChI Key | DYYQDDUCQLULFE-CSMHCCOUSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Keto acids and derivatives |
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Sub Class | Medium-chain keto acids and derivatives |
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Direct Parent | Medium-chain keto acids and derivatives |
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Alternative Parents | |
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Substituents | - Medium-chain keto acid
- Gamma-keto acid
- Branched fatty acid
- Methyl-branched fatty acid
- Hydroxy fatty acid
- Acyloin
- Fatty acyl
- Alpha-hydroxy ketone
- Secondary alcohol
- Ketone
- Carboxylic acid
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | Not Available |
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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 | Not Available |
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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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N-Lactoylisoleucine,1TMS,isomer #1 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O | 1576.8 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TMS,isomer #2 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C | 1560.3 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TMS,isomer #3 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O)C(=O)O | 1646.6 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TMS,isomer #4 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O)C(=O)O | 1634.9 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TMS,isomer #1 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1652.3 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TMS,isomer #2 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C)C(=O)O | 1734.4 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TMS,isomer #3 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O[Si](C)(C)C)C(=O)O | 1701.9 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TMS,isomer #4 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O)C(=O)O[Si](C)(C)C | 1731.6 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TMS,isomer #5 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O)C(=O)O[Si](C)(C)C | 1684.0 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1806.7 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1762.4 | Standard non polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C)=C(C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1711.6 | Standard polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1744.2 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1699.2 | Standard non polar | 33892256 | N-Lactoylisoleucine,3TMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1719.8 | Standard polar | 33892256 | N-Lactoylisoleucine,1TBDMS,isomer #1 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O | 1804.0 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TBDMS,isomer #2 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C(C)(C)C | 1771.4 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TBDMS,isomer #3 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O)C(=O)O | 1904.3 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,1TBDMS,isomer #4 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O)C(=O)O | 1869.1 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TBDMS,isomer #1 | CC[C@@H](C)[C@H](CC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2095.0 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TBDMS,isomer #2 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O | 2196.7 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TBDMS,isomer #3 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O | 2148.8 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TBDMS,isomer #4 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O)C(=O)O[Si](C)(C)C(C)(C)C | 2184.0 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,2TBDMS,isomer #5 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O)C(=O)O[Si](C)(C)C(C)(C)C | 2119.2 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2448.5 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2323.7 | Standard non polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #1 | CC[C@@H](C)[C@H](CC(O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2182.2 | Standard polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2399.8 | Semi standard non polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2265.2 | Standard non polar | 33892256 | N-Lactoylisoleucine,3TBDMS,isomer #2 | CC[C@@H](C)[C@H](C=C(O[Si](C)(C)C(C)(C)C)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2156.6 | Standard 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 - N-Lactoylisoleucine GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dm-9300000000-0a0ad40fb6da26f08334 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Lactoylisoleucine GC-MS (2 TMS) - 70eV, Positive | splash10-014i-9822000000-8fed8f8d06fccbf275d4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Lactoylisoleucine 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 - N-Lactoylisoleucine 10V, Positive-QTOF | splash10-0f79-1930000000-828911aae6b8b1fe23d3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 20V, Positive-QTOF | splash10-0ap0-9500000000-dde74c5abbc47e19fbe5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 40V, Positive-QTOF | splash10-0a59-9100000000-798834d33c3be815ec35 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 10V, Negative-QTOF | splash10-0udi-2590000000-051999c8787bb9931be0 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 20V, Negative-QTOF | splash10-0cdi-4910000000-0c5893e92c641adc1a38 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 40V, Negative-QTOF | splash10-0079-9100000000-93cd80e5b25bac47dd3d | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 10V, Negative-QTOF | splash10-0udi-1690000000-1cb9920efbee46aaabdf | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 20V, Negative-QTOF | splash10-0adi-9500000000-f7520a11022b812a3adc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 40V, Negative-QTOF | splash10-0fdx-9000000000-9229c611ab40c2684ffc | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 10V, Positive-QTOF | splash10-0udi-4940000000-07bcee8333f5086f40a0 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 20V, Positive-QTOF | splash10-003s-9300000000-4a1472aadf43c79a1732 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylisoleucine 40V, Positive-QTOF | splash10-0532-9000000000-07d84492057b8d530233 | 2021-09-24 | 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) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | 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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