Canmetcon
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Identification
YMDB IDYMDB00690
NameL-cysteinylglycine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionCysteinylglycine is a naturally occurring dipeptide. It is breakdown product of glutathione and an intermediate in the gamma-glutamyl cycle. [Biocyc PWY-4041]
Structure
Thumb
Synonyms
  • 5-l-glutamyl-l-cysteinylglycine
  • Agifutol S
  • Bakezyme RX
  • Copren
  • Cys-Gly
  • Cysteinylglycine
  • Deltathione
  • gamma-Glutamylcysteinylglycine
  • gamma-l-glutamyl-l-cysteinyl-glycine
  • gamma-L-Glutamyl-L-cysteinylglycine
  • Glutathion
  • Glutathione
  • Glutathione (reduced type)
  • Glutathione (reduced)
  • Glutathione red
  • Glutathione reduced
  • Glutathione-SH
  • Glutatiol
  • Glutatione
  • Gluthathione
  • Glutide
  • Glutinal
  • GSH
  • Isethion
  • L-Cysteinylglycine
  • L-g-glutamyl-L-cysteinyl-glycine
  • L-gamma-glutamyl-L-cysteinyl-glycine
  • L-gamma-glutamyl-L-cysteinylglycine
  • L-glutamyl-L-cysteinylglycine
  • L-Glutathione
  • L-Glutathione reduce
  • Ledac
  • n-(n-gamma-l-glutamyl-l-cysteinyl)glycine
  • N-L-cysteinylglycine
  • Neuthion
  • red. glutathione
  • Reduced glutathione
  • Tathion
  • Tathione
  • Triptide
  • CG
  • N-Cysteinyl glycine
  • N-Cysteinyl-glycine
  • N-L-Cysteinyl-glycine
  • Cysteinyl-glycine
CAS number70-18-8
WeightAverage: 178.21
Monoisotopic: 178.041212886
InChI KeyZUKPVRWZDMRIEO-VKHMYHEASA-N
InChIInChI=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
IUPAC Name2-[(2R)-2-amino-3-sulfanylpropanamido]acetic acid
Traditional IUPAC NameCys-Gly
Chemical FormulaC5H10N2O3S
SMILESN[C@@H](CS)C(=O)NCC(O)=O
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
Substituents
  • 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
Physical Properties
StateSolid
Charge0
Melting point195 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility6.25 g/LALOGPS
logP-2.6ALOGPS
logP-3.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.6ChemAxon
pKa (Strongest Basic)8.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity41.03 m³·mol⁻¹ChemAxon
Polarizability16.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glutathione metabolismPW002395 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Cysteine and methionine metabolismec00270 Map00270
Glutathione metabolismec00480 Map00480
Pyruvate metabolismec00620 Map00620
SMPDB Reactions
Glutathione + L-CysteineL-cysteinylglycine + Gamma-Glutamylcysteine
L-cysteinylglycine + waterGlycine + L-Cysteine
KEGG Reactions
Glutathione + L-AlanineL-cysteinylglycine + L-gamma-Glutamyl-L-alanine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID4047
HMDB IDHMDB00125
Pubchem Compound ID65270
Kegg IDC00051
ChemSpider ID388596
FOODB IDFDB021891
WikipediaGlutathione
BioCyc IDOXIDIZED-GLUTATHIONE

Enzymes

General function:
Involved in gamma-glutamyltransferase activity
Specific function:
Plays a role in the turnover of the vacuolar glutathione and in the supply of growth requirements during nitrogen starvation
Gene Name:
ECM38
Uniprot ID:
Q05902
Molecular weight:
73179.79688
Reactions
(5-L-glutamyl)-peptide + an amino acid → peptide + 5-L-glutamyl amino acid.