Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:28:54 UTC
Update Date2024-04-30 19:31:49 UTC
Metabolite IDMMDBc0000332
Metabolite Identification
Common NameCysteinylglycine
DescriptionCysteinylglycine 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 (PMID: 8642471 ). 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 (PMID: 16556671 ). 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 (PMID: 15895891 ). 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 (PMID: 15843241 ).
Structure
Synonyms
ValueSource
CGChEBI
Cys-glyChEBI
N-L-CysteinylglycineChEBI
L-CysteinylglycineKegg
N-Cysteinyl glycineHMDB
N-Cysteinyl-glycineHMDB
N-L-Cysteinyl-glycineHMDB
Cysteinyl-glycineHMDB
C-g DipeptideHMDB
CG DipeptideHMDB
Cysteine glycine dipeptideHMDB
Cysteine-glycine dipeptideHMDB
L-Cys-glyHMDB
N-CysteinylglycineHMDB
CysteinylglycineChEBI
Molecular FormulaC5H10N2O3S
Average Mass178.21
Monoisotopic Mass178.041212886
IUPAC Name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
Traditional NameCys-Gly
CAS Registry NumberNot Available
SMILES
N[C@@H](CS)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C5H10N2O3S/c6-3(2-11)5(10)7-1-4(8)9/h3,11H,1-2,6H2,(H,7,10)(H,8,9)/t3-/m0/s1
InChI KeyZUKPVRWZDMRIEO-VKHMYHEASA-N