General Information of MET (ID: META01213)
Name Cys-gly
Synonyms   Click to Show/Hide Synonyms of This Metabolite
7729-20-6; Cys-Gly, oxidized; NSC333711; ((2-Amino-3-((2-amino-3-((carboxymethyl)amino)-3-oxopropyl)dithio)propanoyl)amino)acetic acid; Cys-Gly, oxidised; 2-[[2-amino-3-[[2-amino-3-(carboxymethylamino)-3-oxopropyl]disulfanyl]propanoyl]amino]acetic acid; Cys(Cys-Gly)-Gly; Cys-Gly dimer; Cys-Gly disulfide; NSC 333711; (Cys-Gly)2; SCHEMBL14789149; CHEBI:133040; NSC-333711; 2,2'-{disulfanediylbis[(2-amino-1-oxopropane-3,1-diyl)azanediyl]}diacetic acid; 2-[[2-amino-3-[[2-amino-3-(carboxymethylamino)-3-keto-propyl]disulfanyl]propanoyl]amino]acetic acid; 2-[[2-amino-3-[[2-amino-3-(carboxymethylamino)-3-oxo-propyl]disulfanyl]propanoyl]amino]acetic acid
Source Aliphatic acyclic compounds
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
C10H18N4O6S2
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 354.4 Topological Polar Surface Area 235
XlogP -7.6 Complexity 384
Heavy Atom Count 22 Rotatable Bond Count 11
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 10
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
      Apolipoprotein (Apo)
            Apolipoprotein A-II (APOA2) 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 Mutation (-265T >C(rs5082)) of APOA2
                      Induced Change Cys-gly concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Obesity [ICD-11: 5B81]
                      Details It is reported that mutation (-265T >C(rs5082)) of APOA2 leads to the increase of cys-gly levels compared with control group.
References
1 Epigenomics and metabolomics reveal the mechanism of the APOA2-saturated fat intake interaction affecting obesity. Am J Clin Nutr. 2018 Jul 1;108(1):188-200.

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