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 22:19:44 UTC |
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Update Date | 2021-09-14 15:45:27 UTC |
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HMDB ID | HMDB0062181 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Lactoylvaline |
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Description | N-Lactoylvaline 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)C(NC(=O)[C@H](C)O)C(O)=O InChI=1S/C8H15NO4/c1-4(2)6(8(12)13)9-7(11)5(3)10/h4-6,10H,1-3H3,(H,9,11)(H,12,13)/t5-,6?/m0/s1 |
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Synonyms | Value | Source |
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N-Lactoyl-valine | HMDB |
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Chemical Formula | C8H15NO4 |
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Average Molecular Weight | 189.211 |
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Monoisotopic Molecular Weight | 189.100107967 |
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IUPAC Name | 2-[(2S)-2-hydroxypropanamido]-3-methylbutanoic acid |
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Traditional Name | 2-[(2S)-2-hydroxypropanamido]-3-methylbutanoic acid |
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CAS Registry Number | 21753-44-6 |
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SMILES | CC(C)C(NC(=O)[C@H](C)O)C(O)=O |
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InChI Identifier | InChI=1S/C8H15NO4/c1-4(2)6(8(12)13)9-7(11)5(3)10/h4-6,10H,1-3H3,(H,9,11)(H,12,13)/t5-,6?/m0/s1 |
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InChI Key | IJKKTQLUXOILBQ-ZBHICJROSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. |
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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 | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-alpha-amino acid
- Valine or derivatives
- Branched fatty acid
- Hydroxy fatty acid
- Methyl-branched fatty acid
- Fatty acyl
- Fatty acid
- Secondary alcohol
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxide
- Hydrocarbon derivative
- 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 | |
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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-Lactoylvaline,1TMS,isomer #1 | CC(C)C(NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O | 1568.3 | Semi standard non polar | 33892256 | N-Lactoylvaline,1TMS,isomer #2 | CC(C)C(NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C | 1538.8 | Semi standard non polar | 33892256 | N-Lactoylvaline,1TMS,isomer #3 | CC(C)C(C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C | 1538.0 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TMS,isomer #1 | CC(C)C(NC(=O)[C@H](C)O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1632.0 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TMS,isomer #2 | CC(C)C(C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C | 1634.8 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TMS,isomer #3 | CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C | 1591.4 | Semi standard non polar | 33892256 | N-Lactoylvaline,3TMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C | 1697.4 | Semi standard non polar | 33892256 | N-Lactoylvaline,3TMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C | 1670.5 | Standard non polar | 33892256 | N-Lactoylvaline,3TMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C)[Si](C)(C)C | 1676.1 | Standard polar | 33892256 | N-Lactoylvaline,1TBDMS,isomer #1 | CC(C)C(NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O | 1805.5 | Semi standard non polar | 33892256 | N-Lactoylvaline,1TBDMS,isomer #2 | CC(C)C(NC(=O)[C@H](C)O)C(=O)O[Si](C)(C)C(C)(C)C | 1762.6 | Semi standard non polar | 33892256 | N-Lactoylvaline,1TBDMS,isomer #3 | CC(C)C(C(=O)O)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C | 1773.9 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TBDMS,isomer #1 | CC(C)C(NC(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2072.3 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TBDMS,isomer #2 | CC(C)C(C(=O)O)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2092.3 | Semi standard non polar | 33892256 | N-Lactoylvaline,2TBDMS,isomer #3 | CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O)[Si](C)(C)C(C)(C)C | 2045.9 | Semi standard non polar | 33892256 | N-Lactoylvaline,3TBDMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2334.0 | Semi standard non polar | 33892256 | N-Lactoylvaline,3TBDMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2252.5 | Standard non polar | 33892256 | N-Lactoylvaline,3TBDMS,isomer #1 | CC(C)C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)[C@H](C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2124.6 | 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-Lactoylvaline GC-MS (Non-derivatized) - 70eV, Positive | splash10-0007-9200000000-330034082ecb06695628 | 2017-09-20 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Lactoylvaline GC-MS (2 TMS) - 70eV, Positive | splash10-014i-7920000000-3484e47d4897a6513258 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Lactoylvaline 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-Lactoylvaline 10V, Positive-QTOF | splash10-006x-1900000000-acece8f49c0b3f5c9fac | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 20V, Positive-QTOF | splash10-00dl-9800000000-e5ee123d2b464c1673fa | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 40V, Positive-QTOF | splash10-00di-9200000000-766f8a3c6f476358a7c5 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 10V, Negative-QTOF | splash10-000i-0900000000-223c2e4dabb683271ab3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 20V, Negative-QTOF | splash10-00y0-5900000000-8330910f64cb480efc7b | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 40V, Negative-QTOF | splash10-00di-9200000000-1a15d75ae8a6f04eeb6e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 10V, Negative-QTOF | splash10-000i-0900000000-187ed99fdf54e18dc163 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 20V, Negative-QTOF | splash10-014i-5900000000-6ed40e9b96c346c2bc83 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 40V, Negative-QTOF | splash10-0a4l-9000000000-21f595bb039585a5dbc2 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 10V, Positive-QTOF | splash10-014l-2900000000-d47afbc7153ef4cce63e | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 20V, Positive-QTOF | splash10-0fk9-9700000000-288a5de63d3e071e011f | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Lactoylvaline 40V, Positive-QTOF | splash10-00di-9000000000-9ae7cd304ce71e3a08f2 | 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, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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 |
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General References | - Jansen RS, Addie R, Merkx R, Fish A, Mahakena S, Bleijerveld OB, Altelaar M, IJlst L, Wanders RJ, Borst P, van de Wetering K: N-lactoyl-amino acids are ubiquitous metabolites that originate from CNDP2-mediated reverse proteolysis of lactate and amino acids. Proc Natl Acad Sci U S A. 2015 May 26;112(21):6601-6. doi: 10.1073/pnas.1424638112. Epub 2015 May 11. [PubMed:25964343 ]
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