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Identification
YMDB IDYMDB00252
NameGamma-Glutamylcysteine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiongamma-Glutamylcysteine, also known as L-γ-glutamylcysteine or gamma-glu-cys, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is a very strong basic compound (based on its pKa). gamma-Glutamylcysteine exists in all living species, ranging from bacteria to humans. gamma-Glutamylcysteine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • (Des-Gly)-Glutathione
  • 3GC
  • 5-L-Glutamyl-L-cysteine
  • 5-L-glutamylcysteine
  • g-Glutamylcysteine
  • g-L-Glutamyl-L-cysteine
  • gamma-Glu-cys
  • gamma-Glutamylcysteine
  • gamma-L-Glutamyl-L-cysteine
  • H-gamma-Glu-Cys-OH
  • H-Glu(Cys-OH)-OH
  • L-g-Glutamyl-L-cysteine
  • L-gamma-Glutamyl-L-cysteine
  • L-gamma-Glutamylcysteine
  • N-(1-carboxy-2-mercaptoethyl)-L-Glutamine
  • N-L-gamma-glutamyl-L-Cysteine
  • xN-L-g-glutamyl-Glutamine
  • xN-L-gamma-glutamyl-Glutamine
  • GammaGluCys
  • Glu(-cys)
  • g-Glu-cys
  • Γ-glu-cys
  • Γ-L-glutamyl-L-cysteine
  • L-g-Glutamylcysteine
  • L-Γ-glutamylcysteine
  • Γ-glutamylcysteine
  • Γ-L-glu-L-cys
  • L-Γ-glutamyl-L-cysteine
  • N-Γ-glutamylcysteine
  • N-L-Γ-glutamylcysteine
  • N-L-Γ-glutamyl-L-cysteine
  • gamma-L-Glu-L-cys
  • N-gamma-Glutamylcysteine
  • N-L-gamma-Glutamylcysteine
  • N-Γ-L-glutamyl-L-cysteine
CAS number636-58-8
WeightAverage: 250.272
Monoisotopic: 250.062342258
InChI KeyRITKHVBHSGLULN-WHFBIAKZSA-N
InChIInChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
IUPAC Name(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional IUPAC Namegamma-glutamylcysteine
Chemical FormulaC8H14N2O5S
SMILES[H]OC(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])C(=O)N([H])[C@]([H])(C(=O)O[H])C([H])([H])S[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Cysteine or derivatives
  • Alpha-amino acid
  • L-alpha-amino acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Alkylthiol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.62 g/LALOGPS
logP-2.5ALOGPS
logP-3.8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.91ChemAxon
pKa (Strongest Basic)9.24ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity56.31 m³·mol⁻¹ChemAxon
Polarizability23.36 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
KEGG Pathways
Glutathione metabolismec00480 Map00480
SMPDB Reactions
L-Glutamic acid + L-Cysteine + Adenosine triphosphateADP + phosphate + hydron + Gamma-Glutamylcysteine
Gamma-Glutamylcysteine + Glycine + Adenosine triphosphateADP + phosphate + hydron + Glutathione
Glutathione + L-CysteineL-cysteinylglycine + Gamma-Glutamylcysteine
KEGG Reactions
Adenosine triphosphate + L-Glutamic acid + L-Cysteinephosphate + Gamma-Glutamylcysteine + hydron + ADP
Adenosine triphosphate + Glycine + Gamma-Glutamylcysteinephosphate + Glutathione + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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:Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.
External Links:
ResourceLink
CHEBI ID17515
HMDB IDHMDB01049
Pubchem Compound ID123938
Kegg IDC00669
ChemSpider ID110467
FOODB IDFDB003603
WikipediaGamma-Glutamylcysteine
BioCyc IDL-GAMMA-GLUTAMYLCYSTEINE

Enzymes

General function:
Involved in ATP binding
Specific function:
ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione
Gene Name:
GSH2
Uniprot ID:
Q08220
Molecular weight:
55814.69922
Reactions
ATP + gamma-L-glutamyl-L-cysteine + glycine → ADP + phosphate + glutathione.
General function:
Involved in glutamate-cysteine ligase activity
Specific function:
ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine
Gene Name:
GSH1
Uniprot ID:
P32477
Molecular weight:
78252.89844
Reactions
ATP + L-glutamate + L-cysteine → ADP + phosphate + gamma-L-glutamyl-L-cysteine.
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.