General Information of MET (ID: META00151)
Name Cysteinylglycine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
C-g Dipeptide; CG; CG Dipeptide; Cys-gly; Cysteine glycine dipeptide; Cysteine-glycine dipeptide; Cysteinyl-glycine; Cysteinylglycine; L-Cys-gly; L-Cysteinylglycine; N-Cysteinyl glycine; N-Cysteinyl-glycine; N-Cysteinylglycine; N-L-Cysteinyl-glycine; N-L-Cysteinylglycine
Source Endogenous;Escherichia Coli Metabolite;Food;Microbial
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
439498
HMDB ID
HMDB0000078
Formula
C5H10N2O3S
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C01419
ChEBI ID
4047
FooDB ID
FDB021891
ChemSpider ID
388596
METLIN ID
5134
Physicochemical Properties Molecular Weight 178.21 Topological Polar Surface Area 93.4
XlogP -3.7 Complexity 162
Heavy Atom Count 11 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
Function
Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. It is derived from the breakdown of glutathione (a tripeptide). In plasma, cysteinylglycine is in a reduced, oxidized, and protein-bound form (aminothiol) and interacts via redox and disulphide exchange reactions in a dynamic system referred to as redox thiol status. Spermatozoa of sub-fertile men contain significantly higher thiol concentrations as compared with those of fertile men. The detrimental effect on embryo quality of a high homocysteine (Hcy) concentration in the ejaculate and in the follicular fluid is intriguing and may suggest that Hcy is inversely associated with fertility outcome. Rheumatoid arthritis (RA) is a chronic inflammatory disease which involves the synovial membrane of multiple diarthroidal joints causing damage to cartilage and bones. The damage process seems to be related to an overproduction of oxygen reactive species inducing an oxidative perturbation with an increase in some oxidized forms (disulfides and protein mixed disulfides) and a decrease in free thiols. Imipenem (thienamycin formamidine) is a broad-spectrum beta-lactam antibiotic, always used in combination with cilastatin in order to avoid the premature breakdown of imipenem by renal tubular dipeptidase. As this dipeptidase also hydrolyzes the glutathione metabolite cysteinylglycine, the therapeutic association of imipenem and cilastatin causes plasma levels of cysteinylglycine to increase significantly, while cysteine levels are decreased and homocysteine levels are unaffected. Therefore, antibiotic treatment using imipenem-cilastatin induces important metabolic changes that should not remain unrecognized.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) 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 Knockdown (shRNA) of SULF1
                      Induced Change Cysteinylglycine concentration: increase (FC = 2.09)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of cysteinylglycine levels compared with control group.
      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 [2]
                      Introduced Variation Knockout of TP53
                      Induced Change Cysteinylglycine concentration: decrease (Log2 FC=0.72)
                      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 cysteinylglycine levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

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