ECMDB: gamma-Glutamylcysteine (ECMDB01049) (M2MDB000232)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (352)

Record Information

Version

2.0

Creation Date

2012-05-31 13:03:49 -0600

Update Date

2015-09-13 12:56:09 -0600

Secondary Accession Numbers

ECMDB01049

Identification

Name:

gamma-Glutamylcysteine

Description

G-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 glutamate metabolism pathway (KEGG).

Structure

MOL SDF PDB SMILES InChI

Synonyms:

γ-glutamylcysteine
γ-L-glutamyl-L-cysteine
(Des-Gly)-Glutathione
3GC
5-L-Glutamyl-L-cysteine
5-L-Glutamylcysteine
g-Glu-cys
G-Glutamylcysteine
G-L-Glutamyl-L-cysteine
Gamma-Glu-cys
Gamma-Glutamylcysteine
Gamma-L-Glutamyl-L-cysteine
H-g-Glu-cys-OH
H-gamma-Glu-Cys-OH
H-Glu(Cys-OH)-OH
H-γ-Glu-cys-OH
L-g-Glutamyl-L-cysteine
L-g-Glutamylcysteine
L-gamma-Glutamyl-L-cysteine
L-gamma-Glutamylcysteine
L-γ-Glutamyl-L-cysteine
L-γ-Glutamylcysteine
N-(1-Carboxy-2-mercaptoethyl)-L-Glutamine
N-L-g-Glutamyl-L-cysteine
N-L-gamma-Glutamyl-L-Cysteine
N-L-γ-Glutamyl-L-cysteine
XN-L-g-glutamyl-Glutamine
XN-L-gamma-glutamyl-Glutamine
XN-L-γ-Glutamyl-glutamine
γ-Glu-cys
γ-Glutamylcysteine
γ-L-Glutamyl-L-cysteine

Chemical Formula:

C₈H₁₄N₂O₅S

Weight:

Average: 250.272
Monoisotopic: 250.062342258

InChI Key:

RITKHVBHSGLULN-WHFBIAKZSA-N

InChI:

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

CAS number:

636-58-8

IUPAC Name:

(2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid

Traditional IUPAC Name:

gamma-glutamylcysteine

SMILES:

N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-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 Framework

Aliphatic acyclic compounds

External Descriptors

gamma-glutamylcysteine (CHEBI:17515 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	2.62 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.8	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	1.91	ChemAxon
pKa (Strongest Basic)	9.24	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	129.72 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	56.31 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Glutathione metabolism	PW000833
glutathione metabolism II	PW001927
glutathione metabolism III	PW002018

KEGG Pathways:

Glutathione metabolism ec00480
Metabolic pathways eco01100

EcoCyc Pathways:

glutathione biosynthesis GLUTATHIONESYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-054t-1920100000-5ce9a082971db6d9e2e9	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9630000000-344be03dbe2132b00c88	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-8494000000-88b1eea1e1badaee084b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-50bd1555ededc1afde80	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0290000000-385ca433f03af7530f47	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9510000000-5f29ca903abe05256c83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9510000000-5f29ca903abe05256c83	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-1490000000-bfce673369358b8079e9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0690000000-c49357f0d28683125b6d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002b-2490000000-41c54aabf6acd4d3b53e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014j-9050000000-1137fb3c62232376669c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-1790000000-2aaa1344429a2297cc6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-4920000000-4ad42780853d5599c05b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-9400000000-b67fd0eaf646aa8f47b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-1390000000-e723899e4ca71bda7600	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00sj-3960000000-9a2f96ad7d24e7546315	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00e9-9300000000-e14b428bbb5b63d3ae06	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00b9-0910000000-302a05e4e453b27bad64	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-3900000000-da869ba294aa1d1e7c49	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000x-9100000000-4bc7ff3637ea175068f0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zmi-0960000000-675f718188f5caad73ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9600000000-13ddc5ab8de093dd11ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9100000000-8b8a5550fa1112649784	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Andersson A, Isaksson A, Brattstrom L, Hultberg B: Homocysteine and other thiols determined in plasma by HPLC and thiol-specific postcolumn derivatization. Clin Chem. 1993 Aug;39(8):1590-7. Pubmed: 8353942
Andersson A, Isaksson A, Hultberg B: Homocysteine export from erythrocytes and its implication for plasma sampling. Clin Chem. 1992 Jul;38(7):1311-5. Pubmed: 1623596
Atamna H, Ginsburg H: The malaria parasite supplies glutathione to its host cell--investigation of glutathione transport and metabolism in human erythrocytes infected with Plasmodium falciparum. Eur J Biochem. 1997 Dec 15;250(3):670-9. Pubmed: 9461289
Diaz-Hernandez JI, Almeida A, Delgado-Esteban M, Fernandez E, Bolanos JP: Knockdown of glutamate-cysteine ligase by small hairpin RNA reveals that both catalytic and modulatory subunits are essential for the survival of primary neurons. J Biol Chem. 2005 Nov 25;280(47):38992-9001. Epub 2005 Sep 23. Pubmed: 16183645
Efferth T, Volm M: Glutathione-related enzymes contribute to resistance of tumor cells and low toxicity in normal organs to artesunate. In Vivo. 2005 Jan-Feb;19(1):225-32. Pubmed: 15796179
Iida M, Yasuhara T, Mochizuki H, Takakura H, Yanagisawa T, Kubo H: Two Japanese brothers with hereditary gamma-glutamyl transpeptidase deficiency. J Inherit Metab Dis. 2005;28(1):49-55. Pubmed: 15702405
Kaarteenaho-Wiik R, Kinnula VL: Distribution of antioxidant enzymes in developing human lung, respiratory distress syndrome, and bronchopulmonary dysplasia. J Histochem Cytochem. 2004 Sep;52(9):1231-40. Pubmed: 15314090
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Levonen AL, Lapatto R, Saksela M, Raivio KO: Expression of gamma-glutamylcysteine synthetase during development. Pediatr Res. 2000 Feb;47(2):266-70. Pubmed: 10674357
Lochman P, Adam T, Friedecky D, Hlidkova E, Skopkova Z: High-throughput capillary electrophoretic method for determination of total aminothiols in plasma and urine. Electrophoresis. 2003 Apr;24(7-8):1200-7. Pubmed: 12707912
Lou MF, Dickerson JE Jr, Tung WH, Wolfe JK, Chylack LT Jr: Correlation of nuclear color and opalescence with protein S-thiolation in human lenses. Exp Eye Res. 1999 May;68(5):547-52. Pubmed: 10328968
Martensson J, Kagedal B, Larsson A: Sulphur amino-acid degradation in subjects with hereditary glutathione synthetase deficiency (5-oxoprolinuria). Eur J Clin Invest. 1985 Dec;15(6):371-4. Pubmed: 3938407
Martensson J: Method for determination of free and total glutathione and gamma-glutamylcysteine concentrations in human leukocytes and plasma. J Chromatogr. 1987 Sep 4;420(1):152-7. Pubmed: 3667817
Njalsson R, Ristoff E, Carlsson K, Winkler A, Larsson A, Norgren S: Genotype, enzyme activity, glutathione level, and clinical phenotype in patients with glutathione synthetase deficiency. Hum Genet. 2005 Apr;116(5):384-9. Epub 2005 Feb 17. Pubmed: 15717202
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Zinellu A, Sotgia S, Posadino AM, Pasciu V, Perino MG, Tadolini B, Deiana L, Carru C: Highly sensitive simultaneous detection of cultured cellular thiols by laser induced fluorescence-capillary electrophoresis. Electrophoresis. 2005 Mar;26(6):1063-70. Pubmed: 15706569

Synthesis Reference:

Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	17515
HMDB ID	HMDB01049
Pubchem Compound ID	123938
Kegg ID	C00669
ChemSpider ID	110467
Wikipedia ID	Gamma-Glutamylcysteine
BioCyc ID	L-GAMMA-GLUTAMYLCYSTEINE
EcoCyc ID	L-GAMMA-GLUTAMYLCYSTEINE
Ligand Expo	3GC

Enzymes

Protein Details

1. Glutathione synthetase

General function:: Involved in ATP binding
Specific function:: ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione
Gene Name:: gshB
Uniprot ID:: P04425
Molecular weight:: 35561

Reactions

ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione.

Protein Details

2. Glutamate--cysteine ligase

General function:: Involved in glutamate-cysteine ligase activity
Specific function:: ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine
Gene Name:: gshA
Uniprot ID:: P0A6W9
Molecular weight:: 58269

Reactions

ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine.

gamma-Glutamylcysteine (ECMDB01049) (M2MDB000232)

Structure for #<Compound:0xa4f9078c>

Enzymes

Reactions

Reactions