Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2019-04-04 16:09:28 UTC |
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Update Date | 2022-09-22 17:44:16 UTC |
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HMDB ID | HMDB0240345 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | N2,N5-Diacetylornithine |
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Description | N2,N5-Diacetylornithine, also known as bisorcic, 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. N2,N5-Diacetylornithine is an N-acetyl-L-amino acid that is L-ornithine carrying two acetyl substituents at positions N-2 and N-5. N2,N5-Diacetylornithine was identified as one of forty plasma metabolites that could be used to predict gut microbiome Shannon diversity (PMID: 31477923 ). Shannon diversity is a metric that summarizes both species abundance and evenness, and it has been suggested as a marker for microbiome health. |
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Structure | CC(=O)NCCC[C@H](NC(C)=O)C(O)=O InChI=1S/C9H16N2O4/c1-6(12)10-5-3-4-8(9(14)15)11-7(2)13/h8H,3-5H2,1-2H3,(H,10,12)(H,11,13)(H,14,15)/t8-/m0/s1 |
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Synonyms | Value | Source |
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Bisorcico | ChEBI | Bisorcicum | ChEBI | N(2),N(5)-Diacetylornithine | ChEBI | Bisorcic | HMDB | N2,N5-Diacetyl-L-ornithine | HMDB | N2,N5-Diacetylornithine | HMDB |
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Chemical Formula | C9H16N2O4 |
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Average Molecular Weight | 216.237 |
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Monoisotopic Molecular Weight | 216.111007003 |
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IUPAC Name | (2S)-2,5-diacetamidopentanoic acid |
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Traditional Name | (2S)-2,5-diacetamidopentanoic acid |
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CAS Registry Number | 39825-23-5 |
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SMILES | CC(=O)NCCC[C@H](NC(C)=O)C(O)=O |
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InChI Identifier | InChI=1S/C9H16N2O4/c1-6(12)10-5-3-4-8(9(14)15)11-7(2)13/h8H,3-5H2,1-2H3,(H,10,12)(H,11,13)(H,14,15)/t8-/m0/s1 |
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InChI Key | XUYANFPPYJSBPU-QMMMGPOBSA-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
- Acetamide
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- 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 | 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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N2,N5-Diacetylornithine,1TMS,isomer #1 | CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C | 1938.9 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,1TMS,isomer #2 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O | 1991.1 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,1TMS,isomer #3 | CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C | 1937.3 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1998.8 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1990.6 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 2557.9 | Standard polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C | 1968.6 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C | 1987.5 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C | 2467.0 | Standard polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 1933.1 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 2041.1 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 2530.7 | Standard polar | 33892256 | N2,N5-Diacetylornithine,3TMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 1954.8 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,3TMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 2046.9 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,3TMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C)N(C(C)=O)[Si](C)(C)C)[Si](C)(C)C | 2205.0 | Standard polar | 33892256 | N2,N5-Diacetylornithine,1TBDMS,isomer #1 | CC(=O)NCCC[C@H](NC(C)=O)C(=O)O[Si](C)(C)C(C)(C)C | 2203.0 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,1TBDMS,isomer #2 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O | 2217.1 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,1TBDMS,isomer #3 | CC(=O)NCCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C | 2193.6 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2467.4 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2407.2 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #1 | CC(=O)N[C@@H](CCCN(C(C)=O)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2657.7 | Standard polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C | 2452.3 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C | 2417.1 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #2 | CC(=O)NCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C | 2602.7 | Standard polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2442.9 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2434.2 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,2TBDMS,isomer #3 | CC(=O)N(CCC[C@@H](C(=O)O)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2657.4 | Standard polar | 33892256 | N2,N5-Diacetylornithine,3TBDMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2661.6 | Semi standard non polar | 33892256 | N2,N5-Diacetylornithine,3TBDMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2645.2 | Standard non polar | 33892256 | N2,N5-Diacetylornithine,3TBDMS,isomer #1 | CC(=O)N(CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N(C(C)=O)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2590.4 | 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 - N2,N5-Diacetylornithine 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 - N2,N5-Diacetylornithine 10V, Negative-QTOF | splash10-014i-1290000000-6e78e276c45a4713d277 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Negative-QTOF | splash10-0aw9-7930000000-de76aed8b20891e48b6b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Negative-QTOF | splash10-052f-9000000000-ecdf9cccc78334373356 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 10V, Positive-QTOF | splash10-014i-0890000000-054190e18f43372686ed | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 20V, Positive-QTOF | splash10-0900-2900000000-fa754e72201047cf4edc | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - N2,N5-Diacetylornithine 40V, Positive-QTOF | splash10-03di-9400000000-31a611ad836e3304367b | 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) | 2021-09-25 | Wishart Lab | View Spectrum | 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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 |
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