| Record Information |
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| Version | 1.0 |
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| Creation date | 2011-09-21 00:26:46 UTC |
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| Update date | 2015-07-21 06:57:36 UTC |
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| Primary ID | FDB023239 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Epsilon-(gamma-Glutamyl)-lysine |
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| Description | In non-diabetic kidney scarring the protein crosslinking enzyme tissue transglutaminase (tTg) has been implicated in the process by the formation of increased epsilon-(gamma-glutamyl)lysine bonds between ECM components in both experimental and human disease. Changes in tTg and epsilon-(gamma-glutamyl)lysine occur in human Diabetic nephropathy as well, the leading cause of chronic kidney failure. (PMID 15292688)
In Parkinson's disease (PD), conformational changes in the alpha-synuclein monomer precede the formation of Lewy bodies. Both tTG and its substrate-characteristic N(epsilon)-(gamma-glutamyl)-lysine crosslink are increased in PD nigral dopamine neurons. (PMID 15001552)
Expression of tissue transglutaminase (tTgase) and epsilon-(gamma-glutamyl)-lysine was present in all scarring of the blebs sites, being the main cause of failure in glaucoma filtration surgery. Transglutaminases are calcium-dependent enzymes that catalyze the posttranslational modification of proteins through an acyl transfer reaction between the gamma-carboxamide group of a peptide-bound glutaminyl residue and various amines. Covalent cross-linking using epsilon-(gamma-glutamyl)-lysine bonds is stable and resistant to enzymatic, chemical, and mechanical disruption. (PMID: 16936095) [HMDB] |
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| CAS Number | 17105-15-6 |
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| Structure | |
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| Synonyms | |
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| Predicted Properties | |
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| Chemical Formula | C11H21N3O5 |
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| IUPAC name | (2S)-2-amino-6-[(4S)-4-amino-4-carboxybutanamido]hexanoic acid |
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| InChI Identifier | InChI=1S/C11H21N3O5/c12-7(10(16)17)3-1-2-6-14-9(15)5-4-8(13)11(18)19/h7-8H,1-6,12-13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-/m0/s1 |
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| InChI Key | JPKNLFVGUZRHOB-YUMQZZPRSA-N |
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| Isomeric SMILES | N[C@@H](CCCCNC(=O)CC[C@H](N)C(O)=O)C(O)=O |
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| Average Molecular Weight | 275.3015 |
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| Monoisotopic Molecular Weight | 275.148120797 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Glutamine and derivatives |
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| Alternative Parents | |
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| Substituents | - Glutamine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Dicarboxylic acid or derivatives
- Fatty acyl
- Fatty acid
- Fatty amide
- N-acyl-amine
- Carboxamide group
- Carboxylic acid salt
- Amino acid
- Secondary carboxylic acid amide
- Carboxylic acid
- Organooxygen compound
- Organonitrogen compound
- Organic zwitterion
- Primary aliphatic amine
- Organic salt
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Primary amine
- 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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| Disposition | Biological location: Source: |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Epsilon-(gamma-Glutamyl)-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-001i-5940000000-d882bed3b5529ecff7f9 | Spectrum | | Predicted GC-MS | Epsilon-(gamma-Glutamyl)-lysine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0udi-6639100000-f6ca1e086349e3426243 | Spectrum | | Predicted GC-MS | Epsilon-(gamma-Glutamyl)-lysine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-001i-0490000000-072f36ed9a7b3013d059 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-2930000000-392395a44df2ae8037f8 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9500000000-6e7ed98ff09e19e298dc | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0190000000-58b6ca56f7cccfc512be | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0aba-1690000000-fc6b7fb17538a52f8f98 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006w-9700000000-4409c236d141d5814427 | 2017-09-01 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-05fr-0190000000-87a26493d0e45ab09e99 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0002-1930000000-3595f6a3ff829eac51de | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9500000000-8574eb2f5fa536d0c5ab | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0059-0390000000-6d00013244e4fc3d3d9b | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-001i-9430000000-86b20a12b25ddf059e72 | 2021-09-24 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9200000000-6238074e2599c8441ec5 | 2021-09-24 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 5378717 |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | 7015684 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | Not Available |
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| DrugBank ID | Not Available |
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| HMDB ID | HMDB03869 |
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| CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | Not Available |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | Not Available |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | |
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