Common NameL-cysteinylglycine
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
Molecular FormulaC5H10N2O3S
Average Mass178.21000
Monoisotopic Mass178.04121
IUPAC Name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
Traditional NameCys-gly
CAS Registry Number19246-18-5
SMILES[NH3+][C@@H](CS)C(=O)NCC(=O)[O-]
InChI IdentifierInChI=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
CHEBI IDCHEBI:61694
HMDB IDHMDB0000078
Pathways
NameSMPDB/PathBank
Glutathione metabolism
5-Oxoprolinuria
Gamma-Glutamyltransferase Deficiency
Glutathione Synthetase Deficiency
5-oxoprolinase deficiency
Gamma-glutamyl-transpeptidase deficiency
StateSolid
Water Solubility6.25e+00 g/l
logP-2.59
logS-1.46
pKa (Strongest Acidic)3.60
pKa (Strongest Basic)8.08
Hydrogen Acceptor Count4
Hydrogen Donor Count4
Polar Surface Area92.42 Ų
Rotatable Bond Count4
Physiological Charge0
Formal Charge0
Refractivity41.03 m³·mol⁻¹
Polarizability16.98

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