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 |
|
HMDB ID |
|
Formula |
C5H10N2O3S
|
Structure |
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=439498"></iframe>
|
 |
3D MOL
|
2D MOL
|
|
Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
|
KEGG ID |
|
ChEBI ID |
|
FooDB ID |
|
ChemSpider ID |
|
METLIN ID |
|
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
|
|
|
|
|
|
|
|