Details of Metabolite

General Information of MET (ID: META00844)
Name Epsilon-(gamma-Glutamyl)lysine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
Epsilon-(g-Glutamyl)-lysine; GGEL peptide; L-g-Glutamyl-L-epsilon-lysine; L-gamma-Glutamyl-L-epsilon-lysine; N(6)-L-g-Glutamyl-L-lysine; N(6)-L-gamma-Glutamyl-L-lysine; N(epsilon)-(g-Glutamyl)-lysine; N(epsilon)-(gamma-Glutamyl)-lysine; N-epsilon-(gamma-L-Glutamyl)lysine; Nepsilon(gamma-Glutamyl)lysine; epsilon-(L-g-Glutamyl)-L-lysine; epsilon-(L-gamma-Glutamyl)-L-lysine; epsilon-(g-Glutamyl)lysine; epsilon-(g-L-Glutamyl)-L-lysine; epsilon-(gamma-Glu)-lys; epsilon-(gamma-Glutamyl)-lysine; epsilon-(gamma-Glutamyl)lysine; epsilon-(gamma-Glutamyl)lysine isodipeptide; epsilon-(gamma-L-Glutamyl)-L-lysine; epsilon-(gamma-L-Glutamyl)lysine; g-Glu-epsilon-lys; g-Glutamyl-epsilon-lysine; gamma-Glu-epsilon-lys; gamma-Glutamyl-epsilon-lysine
Source Endogenous;Food
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
7015684
HMDB ID
HMDB0003869
Formula
C11H21N3O5
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
88494
FooDB ID
FDB023239
ChemSpider ID
5378717
Physicochemical Properties Molecular Weight 275.3 Topological Polar Surface Area 165
XlogP -5 Complexity 310
Heavy Atom Count 19 Rotatable Bond Count 8
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Function
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. 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. 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.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of TP53
                      Induced Change epsilon-(gamma-Glutamyl)lysine concentration: decrease (Log2 FC=0.86)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the decrease of epsilon-(gamma-Glutamyl)lysine levels compared with control group.
References
1 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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