Record Information
Creation date2015-10-09 22:33:39 UTC
Update date2017-01-19 02:36:43 UTC
FoodComEx IDPC000976
FoodDB RecordFDB021891
Chemical Information
DescriptionCysteinylglycine, also known as CG or cys-gly, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. 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. Cysteinylglycine is a naturally occurring dipeptide composed of cysteine and glycine. 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. It is derived from the breakdown of glutathione (a tripeptide). Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans. 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). Outside of the human body, Cysteinylglycine has been detected, but not quantified in, several different foods, such as garlics, sweet rowanberries, butternut squash, common oregano, and pepper (c. frutescens). This could make cysteinylglycine a potential biomarker for the consumption of these foods. Cysteinylglycine, with regard to humans, has been linked to the inborn metabolic disorder phenylketonuria.
CAS Number19246-18-5
N-cysteinyl Glycinehmdb
Chemical FormulaC5H10N2O3S
IUPAC name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
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
Isomeric SMILESN[C@@H](CS)C(=O)NCC(O)=O
Average Molecular Weight178.21
Monoisotopic Molecular Weight178.041212886
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
  • Alpha-dipeptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Cysteine or derivatives
  • Alpha-amino acid or derivatives
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Alkylthiol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 4 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
Toronto Research Chemicals C994770