Identification
YMDB IDYMDB00690
NameL-cysteinylglycine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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. Cysteinylglycine is a very strong basic compound (based on its pKa). Cysteinylglycine exists in all living species, ranging from bacteria to humans.
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
  • C-g Dipeptide
  • CG Dipeptide
  • Cysteine glycine dipeptide
  • Cysteine-glycine dipeptide
  • L-Cys-gly
  • N-Cysteinylglycine
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-2980000000-043097e8f1f3f47ff51fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9440000000-ff8b27f3afc92193d83aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-2980000000-043097e8f1f3f47ff51fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9200000000-bae23059b39c80a574a5JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-8920000000-1b3a6e358d6996916b0eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9700000000-6fba6043a24b724b037eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-50e069074067c9f120bdJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-9100000000-ab3327c5b13829ea6d35JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-9700000000-9021340a904a56f317ccJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-5900000000-b9a1082799c427caf10bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9200000000-2b99992e97c6ecb4567bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9000000000-a8b591f7522fe16637fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-0173b5cf52bb61095c3aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00gl-7900000000-f8dc26c3e8b8ec327fc4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kh9-9100000000-410b0cc1b5e3f850b505JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0096-5900000000-55967cd7162376aa6fa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9200000000-5aab410f2c44502defceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9000000000-e0ae26ebba3eeba905daJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-9400000000-1878c834f39272d5af42JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9100000000-0899c0bce2addb667ccbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-05f619b00f6286d67d21JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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.