Showing Metabocard for gamma-L-glutamyl-L-cysteine (BASm0003254)

Common NameGamma-l-glutamyl-l-cysteine
Descriptiongamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG).
Structure
Molecular FormulaC8H14N2O5S
Average Mass250.27200
Monoisotopic Mass250.06234
IUPAC Name(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional NameGlu(-cys)
CAS Registry Number636-58-8
SMILES[NH3+][C@@H](CCC(=O)N[C@@H](CS)C(=O)[O-])C(=O)[O-]
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
CHEBI IDCHEBI:58173
HMDB IDHMDB0001049
Pathways
NameSMPDB/PathBank
Glutathione metabolism
Cysteine Metabolism
Glutamate Metabolism
2-Hydroxyglutric Aciduria (D And L Form)
5-Oxoprolinuria
Gamma-Glutamyltransferase Deficiency
4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency
Glutathione Synthetase Deficiency
Hyperinsulinism-Hyperammonemia Syndrome
Homocarnosinosis
Beta-mercaptolactate-cysteine disulfiduria
5-oxoprolinase deficiency
Gamma-glutamyl-transpeptidase deficiency
Succinic semialdehyde dehydrogenase deficiency
Cystinosis, ocular nonnephropathic
StateSolid
Water Solubility2.62e+00 g/l
logP-2.53
logS-1.98
pKa (Strongest Acidic)1.91
pKa (Strongest Basic)9.24
Hydrogen Acceptor Count6
Hydrogen Donor Count5
Polar Surface Area129.72 Ų
Rotatable Bond Count7
Physiological Charge-1
Formal Charge0
Refractivity56.31 m³·mol⁻¹
Polarizability23.36

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