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Showing Compound gamma-Glutamyl-cysteine (FDB003603)

Record Information
Version1.0
Creation date2010-04-08 22:05:52 UTC
Update date2020-09-17 15:38:47 UTC
Primary IDFDB003603
Secondary Accession Numbers
  • FDB030977
Chemical Information
FooDB 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
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
(des-GLY)-glutathionebiospider
3GCHMDB
5-L-glutamylcysteinebiospider
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-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
Predicted Properties
PropertyValueSource
Water Solubility2.62 g/LALOGPS
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
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
Classification
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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSgamma-Glutamyl-cysteine, non-derivatized, GC-MS Spectrumsplash10-054t-1920100000-5ce9a082971db6d9e2e9Spectrum
GC-MSgamma-Glutamyl-cysteine, non-derivatized, GC-MS Spectrumsplash10-054t-1920100000-5ce9a082971db6d9e2e9Spectrum
Predicted GC-MSgamma-Glutamyl-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-053u-9630000000-344be03dbe2132b00c88Spectrum
Predicted GC-MSgamma-Glutamyl-cysteine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-8494000000-88b1eea1e1badaee084bSpectrum
Predicted GC-MSgamma-Glutamyl-cysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0090000000-50bd1555ededc1afde802012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0290000000-385ca433f03af7530f472012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ue9-5490000000-95d45a9cd2bb6249d3a22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9510000000-5f29ca903abe05256c832012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-001i-9510000000-5f29ca903abe05256c832017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-1490000000-bfce673369358b8079e92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0002-0690000000-c49357f0d28683125b6d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-002b-2490000000-41c54aabf6acd4d3b53e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014j-9050000000-1137fb3c62232376669c2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1790000000-2aaa1344429a2297cc6b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-4920000000-4ad42780853d5599c05b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9400000000-b67fd0eaf646aa8f47b32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-1390000000-e723899e4ca71bda76002016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00sj-3960000000-9a2f96ad7d24e75463152016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-9300000000-e14b428bbb5b63d3ae062016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-0910000000-302a05e4e453b27bad642021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-3900000000-da869ba294aa1d1e7c492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000x-9100000000-4bc7ff3637ea175068f02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zmi-0960000000-675f718188f5caad73ab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9600000000-13ddc5ab8de093dd11ab2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9100000000-8b8a5550fa11126497842021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID110467
ChEMBL IDCHEMBL460831
KEGG Compound IDC00669
Pubchem Compound ID123938
Pubchem Substance IDNot Available
ChEBI ID17515
Phenol-Explorer IDNot Available
DrugBank IDDB03408
HMDB IDHMDB01049
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDGAMMA-GLUTAMYL-CYSTEINE
BIGG ID35655
KNApSAcK IDNot Available
HET ID3GC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glutathione synthetaseGSSP48637
Glutamate--cysteine ligase catalytic subunitGCLCP48506
Gamma-glutamylcyclotransferaseGGCTO75223
Pathways
NameSMPDB LinkKEGG Link
Cysteine MetabolismSMP00013 map00270
Glutamate MetabolismSMP00072 map00250
Glutathione MetabolismSMP00015 map00480
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).