Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-05-23 11:46:43 UTC |
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Update Date | 2023-02-21 17:17:19 UTC |
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HMDB ID | HMDB0006488 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | N-Acetyl-L-glutamate 5-semialdehyde |
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Description | N-Acetyl-L-glutamate 5-semialdehyde, also known as 2-acetamido-5-oxovaleric acid or N-acetyl-5-oxo-L-norvaline, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetyl-L-glutamate 5-semialdehyde exists in all living species, ranging from bacteria to plants to humans. N-Acetyl-L-glutamate 5-semialdehyde has been detected, but not quantified in, several different foods, such as mixed nuts, yams (Dioscorea), bulgur, pepper (capsicum), and wampees (Clausena lansium). This could make N-acetyl-L-glutamate 5-semialdehyde a potential biomarker for the consumption of these foods. N-Acetyl-L-glutamate 5-semialdehyde is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on N-Acetyl-L-glutamate 5-semialdehyde. |
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Structure | CC(=O)N[C@@H](CCC=O)C(O)=O InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1 |
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Synonyms | Value | Source |
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2-Acetamido-5-oxovaleric acid | ChEBI | N-Acetyl-5-oxo-L-norvaline | ChEBI | 2-Acetamido-5-oxopentanoate | Kegg | 2-Acetamido-5-oxovalerate | Generator | 2-Acetamido-5-oxopentanoic acid | Generator | N-Acetyl-L-glutamic acid 5-semialdehyde | Generator | N-Acetyl-L-glutamic acid gamma-semialdehyde | MeSH, HMDB |
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Chemical Formula | C7H11NO4 |
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Average Molecular Weight | 173.1665 |
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Monoisotopic Molecular Weight | 173.068807845 |
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IUPAC Name | (2S)-2-acetamido-5-oxopentanoic acid |
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Traditional Name | N-acetyl-5-oxo-L-norvaline |
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CAS Registry Number | 13074-21-0 |
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SMILES | CC(=O)N[C@@H](CCC=O)C(O)=O |
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InChI Identifier | InChI=1S/C7H11NO4/c1-5(10)8-6(7(11)12)3-2-4-9/h4,6H,2-3H2,1H3,(H,8,10)(H,11,12)/t6-/m0/s1 |
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InChI Key | BCPSFKBPHHBDAI-LURJTMIESA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon 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-L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - N-acyl-l-alpha-amino acid
- Fatty acid
- Alpha-hydrogen aldehyde
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Aldehyde
- Carbonyl group
- Organic nitrogen compound
- Organic oxide
- Hydrocarbon derivative
- 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 | Not Available |
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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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N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #1 | CC(=O)N[C@@H](CCC=O)C(=O)O[Si](C)(C)C | 1540.8 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #2 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O | 1692.8 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,1TMS,isomer #3 | CC(=O)N([C@@H](CCC=O)C(=O)O)[Si](C)(C)C | 1539.5 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1731.9 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1704.3 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2146.6 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1566.5 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1594.2 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1875.3 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1710.8 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1757.1 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 2153.2 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1719.9 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1771.4 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1902.3 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #1 | CC(=O)N[C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C | 1766.9 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #2 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O | 1938.9 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,1TBDMS,isomer #3 | CC(=O)N([C@@H](CCC=O)C(=O)O)[Si](C)(C)C(C)(C)C | 1773.9 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2133.0 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2136.6 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #1 | CC(=O)N[C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2304.2 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2036.7 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2043.7 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #2 | CC(=O)N([C@@H](CCC=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2126.2 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2179.4 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2179.6 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,2TBDMS,isomer #3 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2318.6 | Standard polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2366.2 | Semi standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2406.6 | Standard non polar | 33892256 | N-Acetyl-L-glutamate 5-semialdehyde,3TBDMS,isomer #1 | CC(=O)N([C@@H](CC=CO[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2237.7 | 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-Acetyl-L-glutamate 5-semialdehyde GC-MS (Non-derivatized) - 70eV, Positive | splash10-054o-9500000000-209b524fd8ef1d9e627f | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde GC-MS (1 TMS) - 70eV, Positive | splash10-006x-9420000000-8d264158e366f88d5d3e | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 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-Acetyl-L-glutamate 5-semialdehyde 10V, Positive-QTOF | splash10-05fr-1900000000-cfaeff3cecd86134fd58 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Positive-QTOF | splash10-055r-6900000000-bb54f50a29e9a351858c | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Positive-QTOF | splash10-02a6-9100000000-fe9c1618b7f81c2f9d5b | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Negative-QTOF | splash10-00di-0900000000-f6338ed4d753ef0b744e | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Negative-QTOF | splash10-0m89-3900000000-b5fbc1c314380afa8cc1 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Negative-QTOF | splash10-052f-9100000000-a529029ad524b613c990 | 2015-09-15 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Positive-QTOF | splash10-01q9-0900000000-1f0440fa922d5815c5d9 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Positive-QTOF | splash10-03e9-5900000000-b295f71616c68600654d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Positive-QTOF | splash10-0006-9000000000-0d07a69d508963a4c246 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 10V, Negative-QTOF | splash10-001i-2900000000-d1bb675eb0f08dff7304 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 20V, Negative-QTOF | splash10-01q9-3900000000-a872856bc77482a41b25 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N-Acetyl-L-glutamate 5-semialdehyde 40V, Negative-QTOF | splash10-052f-9000000000-76a9b5ce42ea1d2112d2 | 2021-09-22 | 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) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | 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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