Record Information |
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Version | 1.0 |
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Created at | 2006-08-12 20:14:46 UTC |
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Updated at | 2021-08-19 23:58:26 UTC |
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NP-MRD ID | NP0000761 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | D-Lysine |
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Description | D-Lysine, also known as D-lysin or DLY, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-Lysine exists in all living organisms, ranging from bacteria to humans. D-Lysine is a potentially toxic compound. The D-enantiomer of the alpha-amino acid lysine. |
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Structure | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 |
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Synonyms | Value | Source |
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(R)-2,6-Diaminohexanoic acid | ChEBI | D-2,6-Diaminohexanoic acid | ChEBI | D-Lysin | ChEBI | DLY | ChEBI | (R)-2,6-Diaminohexanoate | Generator | D-2,6-Diaminohexanoate | Generator |
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Chemical Formula | C6H14N2O2 |
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Average Mass | 146.1900 Da |
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Monoisotopic Mass | 146.10553 Da |
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IUPAC Name | (2R)-2,6-diaminohexanoic acid |
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Traditional Name | D-lysine |
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CAS Registry Number | 923-27-3 |
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SMILES | NCCCC[C@@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 |
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InChI Key | KDXKERNSBIXSRK-RXMQYKEDSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-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 | D-alpha-amino acids |
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Alternative Parents | |
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Substituents | - D-alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Fatty acid
- Fatty acyl
- Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organic nitrogen compound
- Amine
- Hydrocarbon derivative
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Wakisaka K, Arano Y, Uezono T, Akizawa H, Ono M, Kawai K, Ohomomo Y, Nakayama M, Saji H: A novel radioiodination reagent for protein radiopharmaceuticals with L-lysine as a plasma-stable metabolizable linkage to liberate m-iodohippuric acid after lysosomal proteolysis. J Med Chem. 1997 Aug 1;40(16):2643-52. [PubMed:9258371 ]
- Darling PB, Bross R, Wykes LJ, Ball RO, Pencharz PB: Isotopic enrichment of amino acids in urine following oral infusions of L-[1-(13)C]phenylalanine and L-[1-(13)C]lysine in humans: confounding effect of D-[13C]amino acids. Metabolism. 1999 Jun;48(6):732-7. [PubMed:10381147 ]
- Bross R, Ball RO, Pencharz PB: Development of a minimally invasive protocol for the determination of phenylalanine and lysine kinetics in humans during the fed state. J Nutr. 1998 Nov;128(11):1913-9. [PubMed:9808642 ]
- Hayman MW, Smith KH, Cameron NR, Przyborski SA: Growth of human stem cell-derived neurons on solid three-dimensional polymers. J Biochem Biophys Methods. 2005 Mar 31;62(3):231-40. Epub 2004 Dec 30. [PubMed:15733583 ]
- Zhang L, Min J, Zhang L: Studies on the synthesis and properties of new PNA analogs consisting of L- and D-lysine backbones. Bioorg Med Chem Lett. 1999 Oct 18;9(20):2903-8. doi: 10.1016/s0960-894x(99)00514-4. [PubMed:10571145 ]
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