Record Information |
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Version | 1.0 |
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Created at | 2006-09-13 12:54:17 UTC |
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Updated at | 2021-06-30 02:06:04 UTC |
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NP-MRD ID | NP0000978 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Aspartyllysine |
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Description | Aspartyllysine is a hydrophilic dipeptide composed of aspartic acid and lysine. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. Aspartyllysine is widely distributed in nature and is present in wheat, fish, and other nutrients. It has been demonstrated to be absorbed by the intestinal H+/peptide transporter PepT1. It is excreted by the kidney-specific high-affinity H+/peptide cotransport system (PMID:1982012 , 9922316 , 7589991 ). |
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Structure | NCCCC[C@H](NC(=O)[C@@H](N)CC(O)=O)C(O)=O InChI=1S/C10H19N3O5/c11-4-2-1-3-7(10(17)18)13-9(16)6(12)5-8(14)15/h6-7H,1-5,11-12H2,(H,13,16)(H,14,15)(H,17,18)/t6-,7-/m0/s1 |
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Synonyms | Value | Source |
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Alpha-Aspartyl-lysine | ChEBI | alpha-Aspartyllysine | ChEBI | DK | ChEBI | L-alpha-Asp-L-lys | ChEBI | L-Asp-L-lys | ChEBI | a-Aspartyl-lysine | Generator | Α-aspartyl-lysine | Generator | a-Aspartyllysine | Generator | Α-aspartyllysine | Generator | L-a-Asp-L-lys | Generator | L-Α-asp-L-lys | Generator | alpha-Asp-lys | HMDB | L-Aspartyl-L-lysine | HMDB | N2-L-a-Aspartyl-L-lysine | HMDB | N2-L-alpha-Aspartyl-L-lysine | HMDB | N-epsilon-(beta-Aspartyl)lysine | HMDB | beta-Aspartyl-epsilon-lysine | HMDB | Asp-lys | HMDB | Aspartate lysine dipeptide | HMDB | Aspartate-lysine dipeptide | HMDB | Aspartic acid lysine dipeptide | HMDB | Aspartic acid-lysine dipeptide | HMDB | Aspartyl-lysine | HMDB | D-K Dipeptide | HMDB | DK Dipeptide | HMDB | L-alpha-Aspartyl-L-lysine | HMDB | L-Α-aspartyl-L-lysine | HMDB | N2-Aspartyllysine | HMDB | N2-L-Aspartyl-L-lysine | HMDB | N2-L-alpha-Aspartyllysine | HMDB | N2-L-Α-aspartyl-L-lysine | HMDB | N2-L-Α-aspartyllysine | HMDB | N2-alpha-Aspartyllysine | HMDB | N2-alpha-L-Aspartyl-L-lysine | HMDB | N2-Α-aspartyllysine | HMDB | N2-Α-L-aspartyl-L-lysine | HMDB | alpha-L-Asp-L-lys | HMDB | alpha-L-Aspartyl-L-lysine | HMDB | Α-asp-lys | HMDB | Α-L-asp-L-lys | HMDB | Α-L-aspartyl-L-lysine | HMDB | Aspartyllysine | ChEBI |
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Chemical Formula | C10H19N3O5 |
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Average Mass | 261.2750 Da |
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Monoisotopic Mass | 261.13247 Da |
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IUPAC Name | (2S)-6-amino-2-[(2S)-2-amino-3-carboxypropanamido]hexanoic acid |
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Traditional Name | L-aspartyl-l-lysine |
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CAS Registry Number | 5891-51-0 |
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SMILES | NCCCC[C@H](NC(=O)[C@@H](N)CC(O)=O)C(O)=O |
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InChI Identifier | InChI=1S/C10H19N3O5/c11-4-2-1-3-7(10(17)18)13-9(16)6(12)5-8(14)15/h6-7H,1-5,11-12H2,(H,13,16)(H,14,15)(H,17,18)/t6-,7-/m0/s1 |
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InChI Key | OAMLVOVXNKILLQ-BQBZGAKWSA-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 | 13C NMR Spectrum (1D, 252 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 | 13C NMR Spectrum (1D, 75 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 | 13C NMR Spectrum (1D, 126 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 | 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 |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | Animalia Plantae |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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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 | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Aspartic acid or derivatives
- N-acyl-l-alpha-amino acid
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Alpha-amino acid or derivatives
- Medium-chain fatty acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Fatty acid
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Secondary carboxylic acid amide
- Carboxylic acid
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxygen compound
- Organic oxide
- Organic nitrogen compound
- Carbonyl group
- Organopnictogen compound
- Amine
- Primary amine
- Organonitrogen compound
- Organooxygen compound
- 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 | 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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Predicted Properties | |
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General References | - Yasumoto K, Suzuki F: Aspartyl- and glutamyl-lysine crosslinks formation and their nutritional availability. J Nutr Sci Vitaminol (Tokyo). 1990;36 Suppl 1:S71-7. [PubMed:1982012 ]
- Shiraga T, Miyamoto K, Tanaka H, Yamamoto H, Taketani Y, Morita K, Tamai I, Tsuji A, Takeda E: Cellular and molecular mechanisms of dietary regulation on rat intestinal H+/Peptide transporter PepT1. Gastroenterology. 1999 Feb;116(2):354-62. [PubMed:9922316 ]
- Brandsch M, Brandsch C, Prasad PD, Ganapathy V, Hopfer U, Leibach FH: Identification of a renal cell line that constitutively expresses the kidney-specific high-affinity H+/peptide cotransporter. FASEB J. 1995 Nov;9(14):1489-96. [PubMed:7589991 ]
- Bagriantseva OV, Kalamkarova LI, Rokutova AV, Aznametova GK, Idrisova RS: [The diagnosis of intestinal dysbacteriosis by the spectrum of fecal amino acids]. Zh Mikrobiol Epidemiol Immunobiol. 1999 Jul-Aug;(4):67-9. [PubMed:10852057 ]
- Tobey NA, Lyn-Cook LE, Ulshen MH, Heizer WD: Intestinal brush border peptidases: activities in normal and abnormal peroral intestinal biopsy specimens. J Lab Clin Med. 1986 Mar;107(3):221-7. [PubMed:2869093 ]
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