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Identification
YMDB IDYMDB00691
NameL-gamma-Glutamyl-L-alanine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptiongamma-Glutamylalanine, also known as 5-L-glutamyl-L-alanine or L-gamma-glu-L-ala, 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. gamma-Glutamylalanine is a very strong basic compound (based on its pKa). gamma-Glutamylalanine exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • (5-L-Glutamyl)-L-amino acid
  • 5-L-glutamylalanine
  • g-Glu-Ala
  • g-Glutamylalanine
  • g-L-Glutamyl-L-alanine
  • gamma-Gln-Ala
  • gamma-Glu-Ala
  • gamma-Glutamylalanine
  • gamma-L-Glutamyl-L-alanine
  • L-gamma-Glutamyl-L-amino acid
  • N-L-gamma-glutamyl-L-alanine
  • 5-L-Glutamyl-L-alanine
  • L-gamma-Glu-L-ala
  • Γ-L-glutamyl-L-alanine
  • L-g-Glu-L-ala
  • L-Γ-glu-L-ala
  • N-L-g-Glutamyl-L-alanine
  • N-L-Γ-glutamyl-L-alanine
  • Γ-glutamylalanine
  • gamma-Glutamylalanine, (D-GLN)-isomer
  • Γ-glu-ala
  • Γ-L-glu-L-ala
  • L-Γ-glutamyl-L-alanine
  • N-Γ-glutamylalanine
  • N-L-Γ-glutamylalanine
  • gamma-L-Glu-L-ala
  • L-gamma-Glutamyl-L-alanine
  • N-gamma-Glutamylalanine
  • N-L-gamma-Glutamylalanine
  • N-Γ-L-glutamyl-L-alanine
  • N-gamma-L-Glutamyl-L-alanine
CAS number5875-41-2
WeightAverage: 218.2072
Monoisotopic: 218.090271568
InChI KeyWQXXXVRAFAKQJM-WHFBIAKZSA-N
InChIInChI=1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
IUPAC Name(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acid
Traditional IUPAC Nameg-glu-ala
Chemical FormulaC8H14N2O5
SMILESC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(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
  • Gamma-glutamyl alpha-amino acid
  • Glutamine or derivatives
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alanine or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Dicarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Primary amine
  • Organonitrogen compound
  • Organooxygen 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 Solubility12.9 g/LALOGPS
logP-3.4ALOGPS
logP-3.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.93ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity48.59 m³·mol⁻¹ChemAxon
Polarizability20.94 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 ReactionsNot Available
KEGG Reactions
Glutathione + L-AlanineL-cysteinylglycine + L-gamma-Glutamyl-L-alanine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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 ID50619
HMDB IDHMDB06248
Pubchem Compound ID440103
Kegg IDC03740
ChemSpider ID389104
FOODB IDFDB023860
Wikipedia IDNot Available
BioCyc IDNot Available

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.