Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2009-04-06 16:20:03 UTC |
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Update Date | 2023-02-21 17:17:40 UTC |
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HMDB ID | HMDB0012150 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 2-Keto-6-acetamidocaproate |
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Description | 2-Keto-6-acetamidocaproate is an intermediate in lysine degradation. It can be generated from N6-acetyl-L-lysine. N-acetyl-lysine is an acetylated amino acid. Post-translational lysine-acetylation is one of two major modifications of lysine residues in various proteins. Acetylation of specific lysine residues in the N-terminal domains of core histones is a biochemical marker of active genes. Acetylation is now known to play a major role in eukaryotic transcription. Specifically, acetyltransferase enzymes that act on particular lysine side chains of histones and other proteins are intimately involved in transcriptional activation. N6-acetyl-L-lysine can be converted to 2-Keto-6-acetamidocaproate via the enzyme N6-acetyllysine aminotransferase and then 2-keto-6-acetamidocaproate can be reduced enzymatically to 5-acetamidovalerate. |
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Structure | InChI=1S/C8H13NO4/c1-6(10)9-5-3-2-4-7(11)8(12)13/h2-5H2,1H3,(H,9,10)(H,12,13) |
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Synonyms | Value | Source |
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2-Keto-6-acetamidocaproic acid | ChEBI | 2-Keto-6-acetamidohexanoic acid | ChEBI | 2-oxo-6-Acetamidocaproic acid | ChEBI | 2-oxo-6-Acetamidocaproate | Kegg | 2-Keto-6-acetamidohexanoate | Generator | 3-Keto-6-acetamidohexanoate | MeSH | 6-acetamido-2-Oxohexanoate | HMDB, Generator | 6-acetamido-2-Oxohexanoic acid | HMDB | 2-Keto-6-acetamidocaproate | Generator |
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Chemical Formula | C8H13NO4 |
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Average Molecular Weight | 187.1931 |
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Monoisotopic Molecular Weight | 187.084457909 |
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IUPAC Name | 6-acetamido-2-oxohexanoic acid |
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Traditional Name | 6-acetamido-2-oxohexanoic acid |
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CAS Registry Number | Not Available |
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SMILES | CC(=O)NCCCCC(=O)C(O)=O |
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InChI Identifier | InChI=1S/C8H13NO4/c1-6(10)9-5-3-2-4-7(11)8(12)13/h2-5H2,1H3,(H,9,10)(H,12,13) |
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InChI Key | NGCXIFFZXAZRAF-UHFFFAOYSA-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
- Amino fatty acid
- Alpha-keto acid
- Fatty acyl
- Alpha-hydroxy ketone
- Acetamide
- Carboxamide group
- Ketone
- Secondary carboxylic acid amide
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organonitrogen compound
- Organic oxide
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Organooxygen compound
- Organic oxygen compound
- 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 | Not Available |
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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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2-Keto-6-acetamidocaproate,1TMS,isomer #1 | CC(=O)NCCCCC(=O)C(=O)O[Si](C)(C)C | 1753.8 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,1TMS,isomer #2 | CC(=O)NCCCC=C(O[Si](C)(C)C)C(=O)O | 1880.6 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,1TMS,isomer #3 | CC(=O)N(CCCCC(=O)C(=O)O)[Si](C)(C)C | 1827.4 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1906.0 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1847.3 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2138.2 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1804.2 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1789.7 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 2008.6 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1914.9 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 1944.6 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O)[Si](C)(C)C | 2224.9 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,3TMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1873.5 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,3TMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1897.6 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,3TMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C | 1923.2 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,1TBDMS,isomer #1 | CC(=O)NCCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C | 2034.4 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,1TBDMS,isomer #2 | CC(=O)NCCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O | 2136.8 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,1TBDMS,isomer #3 | CC(=O)N(CCCCC(=O)C(=O)O)[Si](C)(C)C(C)(C)C | 2039.2 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2388.8 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2236.9 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #1 | CC(=O)NCCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2327.4 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2272.2 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2229.2 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #2 | CC(=O)N(CCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2264.9 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2369.1 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2322.6 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,2TBDMS,isomer #3 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C | 2398.9 | Standard polar | 33892256 | 2-Keto-6-acetamidocaproate,3TBDMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2544.2 | Semi standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,3TBDMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2442.4 | Standard non polar | 33892256 | 2-Keto-6-acetamidocaproate,3TBDMS,isomer #1 | CC(=O)N(CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2322.4 | 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 - 2-Keto-6-acetamidocaproate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9200000000-d77cc429a6b80831b2e4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Keto-6-acetamidocaproate GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9120000000-24931882682cc9ca4557 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Keto-6-acetamidocaproate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 2-Keto-6-acetamidocaproate 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 - 2-Keto-6-acetamidocaproate 10V, Positive-QTOF | splash10-00g4-0900000000-6d348a4fb73306ffc1cc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 20V, Positive-QTOF | splash10-00ba-4900000000-59ff96e4bdcba1a928c6 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 40V, Positive-QTOF | splash10-0abc-9100000000-ceec5d761829d1e1d9b4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 10V, Negative-QTOF | splash10-000l-1900000000-4b2f9cf7c679af8556dc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 20V, Negative-QTOF | splash10-0006-3900000000-ccfc2e6d68e971b0dde3 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 40V, Negative-QTOF | splash10-0a4l-9000000000-6d27ffe991d97f72e3f8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 10V, Negative-QTOF | splash10-000i-1900000000-4b397e6e0e66676db95c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 20V, Negative-QTOF | splash10-0a4i-9600000000-79719ba078d6d91f68d8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 40V, Negative-QTOF | splash10-052f-9000000000-6e1d74558f5e97910e39 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 10V, Positive-QTOF | splash10-03dr-3900000000-cd27d484decdb85b9ec6 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 20V, Positive-QTOF | splash10-0a4i-9100000000-c0fbc4e876c6503b4883 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 2-Keto-6-acetamidocaproate 40V, Positive-QTOF | splash10-0a4i-9000000000-54ba22f9aeb5e3d15cb6 | 2021-09-22 | 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) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | 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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