Record Information
Version1.0
Created at2020-04-17 18:46:08 UTC
Updated at2020-12-07 19:11:10 UTC
CannabisDB IDCDB004878
Secondary Accession NumbersNot Available
Cannabis Compound 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. 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. gamma-Glutamylcysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight250.27
Monoisotopic Molecular Weight250.0623
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSgamma-Glutamylcysteine, non-derivatized, GC-MS Spectrumsplash10-054t-1920100000-5ce9a082971db6d9e2e9Spectrum
GC-MSgamma-Glutamylcysteine, non-derivatized, GC-MS Spectrumsplash10-054t-1920100000-5ce9a082971db6d9e2e9Spectrum
Predicted GC-MSgamma-Glutamylcysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053u-9630000000-344be03dbe2132b00c88Spectrum
Predicted GC-MSgamma-Glutamylcysteine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-8494000000-88b1eea1e1badaee084bSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-50bd1555ededc1afde80Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0290000000-385ca433f03af7530f47Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9510000000-5f29ca903abe05256c83Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9510000000-5f29ca903abe05256c83Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-1390000000-e723899e4ca71bda7600Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00sj-3960000000-9a2f96ad7d24e7546315Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9300000000-e14b428bbb5b63d3ae06Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1790000000-2aaa1344429a2297cc6bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4920000000-4ad42780853d5599c05bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9400000000-b67fd0eaf646aa8f47b3Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Glutamate--cysteine ligase catalytic subunitGCLC6p12P48506 details
Glutaminyl-peptide cyclotransferaseQPCT2p22.2Q16769 details
Glutathione synthetaseGSS20q11.2P48637 details
Gamma-glutamylcyclotransferaseGGCT7p15-p14O75223 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Glutaminyl-peptide cyclotransferaseQPCT2p22.2Q16769 details
ReceptorsNot Available
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Glutamate--cysteine ligase catalytic subunitGCLC6p12P48506 details
Concentrations Data
Not Available
HMDB IDHMDB0001049
DrugBank IDDB03408
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

Enzymes

General function:
Involved in glutamate-cysteine ligase activity
Specific function:
Not Available
Gene Name:
GCLC
Uniprot ID:
P48506
Molecular weight:
68629.42
General function:
Involved in peptidase activity
Specific function:
Responsible for the biosynthesis of pyroglutamyl peptides. Has a bias against acidic and tryptophan residues adjacent to the N-terminal glutaminyl residue and a lack of importance of chain length after the second residue. Also catalyzes N-terminal pyroglutamate formation. In vitro, catalyzes pyroglutamate formation of N-terminally truncated form of APP amyloid-beta peptides [Glu-3]-beta-amyloid. May be involved in the N-terminal pyroglutamate formation of several amyloid-related plaque-forming peptides.
Gene Name:
QPCT
Uniprot ID:
Q16769
Molecular weight:
40876.14
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GSS
Uniprot ID:
P48637
Molecular weight:
52384.325
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:
O75223
Molecular weight:
19091.635