Showing metabocard for Gamma-Glutamylcysteine (BMDB0001049)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (4) Show 4 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:40:22 UTC
Update Date2020-05-21 16:28:25 UTC
BMDB IDBMDB0001049
Secondary Accession Numbers
  • BMDB01049
Metabolite Identification
Common NameGamma-Glutamylcysteine
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
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-L-Glutamyl-L-cysteineChEBI
gamma-Glu-cysChEBI
gamma-L-Glutamyl-L-cysteineChEBI
L-gamma-GlutamylcysteineChEBI
g-Glu-cysGenerator
Γ-glu-cysGenerator
g-L-Glutamyl-L-cysteineGenerator
Γ-L-glutamyl-L-cysteineGenerator
L-g-GlutamylcysteineGenerator
L-Γ-glutamylcysteineGenerator
g-GlutamylcysteineGenerator
Γ-glutamylcysteineGenerator
Γ-L-glu-L-cysHMDB
L-Γ-glutamyl-L-cysteineHMDB
N-Γ-glutamylcysteineHMDB
N-L-Γ-glutamylcysteineHMDB
N-L-Γ-glutamyl-L-cysteineHMDB
gamma-L-Glu-L-cysHMDB
L-gamma-Glutamyl-L-cysteineHMDB
N-gamma-GlutamylcysteineHMDB
N-L-gamma-GlutamylcysteineHMDB
N-L-gamma-Glutamyl-L-cysteineHMDB
5-L-GlutamylcysteineHMDB
H-gamma-Glu-cys-OHHMDB
L-g-Glutamyl-L-cysteineHMDB
N-Γ-L-glutamyl-L-cysteineHMDB
gamma-GlutamylcysteineHMDB
Chemical FormulaC8H14N2O5S
Average Molecular Weight250.272
Monoisotopic Molecular Weight250.062342258
IUPAC Name(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional Namegamma-glutamylcysteine
CAS Registry Number636-58-8
SMILES
N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
InChI Identifier
InChI=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
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
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Fibroblasts
  • Liver
  • Neuron
  • Placenta
  • Prostate Tissue
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
NeuronExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001049
DrugBank IDDB03408
Phenol Explorer Compound IDNot Available
FooDB IDFDB003603
KNApSAcK IDC00007507
Chemspider ID110467
KEGG Compound IDC00669
BioCyc IDL-GAMMA-GLUTAMYLCYSTEINE
BiGG ID35655
Wikipedia LinkGamma-Glutamylcysteine
METLIN ID5966
PubChem Compound123938
PDB IDNot Available
ChEBI ID17515
References
Synthesis ReferenceBridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Glutathione synthetase
General function:
Involved in ATP binding
Specific function:
Not Available
Gene Name:
GSS
Uniprot ID:
Q5EAC2
Molecular weight:
52066.0
Reactions
Adenosine triphosphate + Gamma-Glutamylcysteine + Glycine → ADP + Hydrogen phosphate + Glutathionedetails
Gamma-Glutamylcysteine + Adenosine triphosphate + Glycine → Glutathione + ADP + Hydrogen phosphatedetails
Enzyme Details
2. Glutamate-cysteine ligase catalytic subunit
General function:
Involved in ADP binding
Specific function:
Not Available
Gene Name:
GCLC
Uniprot ID:
Q32S38
Molecular weight:
69023.0
Reactions
Adenosine triphosphate + L-Glutamic acid + L-Cysteine → ADP + Hydrogen phosphate + Gamma-Glutamylcysteinedetails
L-Glutamic acid + Adenosine triphosphate + L-Cysteine → Gamma-Glutamylcysteine + Adenosine diphosphate ribose + Hydrogen phosphatedetails
Enzyme Details
3. Gamma-glutamylcyclotransferase
General function:
Involved in acyltransferase activity
Specific function:
Catalyzes the formation of 5-oxoproline from gamma-glutamyl dipeptides and may play a significant role in glutathione homeostasis. Induces release of cytochrome c from mitochondria with resultant induction of apoptosis.
Gene Name:
GGCT
Uniprot ID:
Q32LE4
Molecular weight:
21177.0
Reactions
Gamma-Glutamylcysteine → L-Cysteine + Pyroglutamic aciddetails
Enzyme Details
4. Glutamate--cysteine ligase regulatory subunit
General function:
Not Available
Specific function:
Not Available
Gene Name:
GCLM
Uniprot ID:
Q2T9Y6
Molecular weight:
30533.0
Reactions
Adenosine triphosphate + L-Glutamic acid + L-Cysteine → ADP + Hydrogen phosphate + Gamma-Glutamylcysteinedetails
L-Glutamic acid + Adenosine triphosphate + L-Cysteine → Gamma-Glutamylcysteine + Adenosine diphosphate ribose + Hydrogen phosphatedetails