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gamma-Glutamyl-cysteine (PC000421)

Record Information
Version1.0
Creation date2015-10-09 22:30:37 UTC
Update date2017-01-19 02:36:22 UTC
FoodComEx IDPC000421
FoodDB RecordFDB003603
Chemical Information
Namegamma-Glutamyl-cysteine
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. Outside of the human body, gamma-Glutamylcysteine has been detected, but not quantified in, several different foods, such as hyssops, rapes, black mulberries, red raspberries, and wild carrots. This could make gamma-glutamylcysteine a potential biomarker for the consumption of these foods. gamma-Glutamylcysteine is a potentially toxic compound. A molecular entity formed when L-cysteine amino group binds to the gamma-carbonyl of L-glutamic acid.
CAS Number636-58-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(des-GLY)-glutathionebiospider
3GCHMDB
5-L-Glutamyl-L-cysteinebiospider
5-L-glutamylcysteinebiospider
g-Glu-cysGenerator
G-glutamylcysteinebiospider
G-l-glutamyl-l-cysteinebiospider
Gamma-glu-CYSbiospider
Gamma-glutamylcysteinebiospider
Gamma-l-glutamyl-l-cysteinebiospider
GammaGluCysChEBI
Glu(-CYS)biospider
H-gamma-glu-CYS-ohbiospider
H-glu(CYS-oh)-ohbiospider
L-cysteine, n-l-gamma-glutamyl-biospider
L-g-glutamyl-l-cysteinebiospider
L-g-GlutamylcysteineGenerator
L-gamma-glutamyl-l-cysteinebiospider
L-gamma-glutamylcysteinebiospider
L-γ-glutamyl-L-cysteineGenerator
L-γ-glutamylcysteineGenerator
N-(1-carboxy-2-mercaptoethyl)-L-Glutaminebiospider
N-l-gamma-glutamyl-l-cysteinebiospider
XN-l-g-glutamyl-glutaminebiospider
XN-l-gamma-glutamyl-glutaminebiospider
γ-glu-cysGenerator
γ-glutamylcysteineGenerator
γ-L-glutamyl-L-cysteineGenerator
Chemical FormulaC8H14N2O5S
IUPAC name(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
InChI IdentifierInChI=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
InChI KeyRITKHVBHSGLULN-WHFBIAKZSA-N
Isomeric SMILESN[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
Average Molecular Weight250.272
Monoisotopic Molecular Weight250.062342258
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available