| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-12 15:20:31 UTC |
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| Updated at | 2022-05-12 15:20:31 UTC |
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| NP-MRD ID | NP0136671 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Tryptophyl-Lysine |
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| Description | Tryptophyl-Lysine, also known as W-K dipeptide or TRP-lys, 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. Tryptophyl-Lysine is a very strong basic compound (based on its pKa). It is an incomplete breakdown product of protein digestion or protein catabolism. Tryptophyl-Lysine is a dipeptide composed of tryptophan and lysine. This dipeptide has not yet been identified in human tissues or biofluids and so it is classified as an 'Expected' metabolite. Tryptophyl-Lysine was first documented in 1985 (PMID: 4052400). 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 (PMID: 4052401). |
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| Structure | NCCCCC(NC(=O)C(N)CC1=CNC2=C1C=CC=C2)C(O)=O InChI=1S/C17H24N4O3/c18-8-4-3-7-15(17(23)24)21-16(22)13(19)9-11-10-20-14-6-2-1-5-12(11)14/h1-2,5-6,10,13,15,20H,3-4,7-9,18-19H2,(H,21,22)(H,23,24) |
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| Synonyms | | Value | Source |
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| L-Tryptophyl-L-lysine | HMDB | | TRP-Lys | HMDB | | Tryptophan lysine dipeptide | HMDB | | Tryptophan-lysine dipeptide | HMDB | | Tryptophyllysine | HMDB | | W-K Dipeptide | HMDB | | WK Dipeptide | HMDB | | 6-Amino-2-{[2-amino-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}hexanoate | Generator |
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| Chemical Formula | C17H24N4O3 |
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| Average Mass | 332.3975 Da |
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| Monoisotopic Mass | 332.18484 Da |
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| IUPAC Name | 6-amino-2-[2-amino-3-(1H-indol-3-yl)propanamido]hexanoic acid |
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| Traditional Name | 6-amino-2-[2-amino-3-(1H-indol-3-yl)propanamido]hexanoic acid |
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| CAS Registry Number | Not Available |
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| SMILES | NCCCCC(NC(=O)C(N)CC1=CNC2=C1C=CC=C2)C(O)=O |
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| InChI Identifier | InChI=1S/C17H24N4O3/c18-8-4-3-7-15(17(23)24)21-16(22)13(19)9-11-10-20-14-6-2-1-5-12(11)14/h1-2,5-6,10,13,15,20H,3-4,7-9,18-19H2,(H,21,22)(H,23,24) |
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| InChI Key | DZHDVYLBNKMLMB-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | 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 | 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, 400 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, 500 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 | 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, 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 | 13C NMR Spectrum (1D, 201 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, 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 | Not Available |
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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
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Triptan
- Alpha-amino acid or derivatives
- 3-alkylindole
- Indole
- Indole or derivatives
- Medium-chain fatty acid
- Amino fatty acid
- Heterocyclic fatty acid
- Aralkylamine
- Fatty amide
- Substituted pyrrole
- Fatty acyl
- Fatty acid
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Organoheterocyclic compound
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Azacycle
- Organonitrogen compound
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Primary amine
- Amine
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Not Available |
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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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