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Human Metabolome Database Version 3.5

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Showing metabocard for Gamma-Glutamylcysteine (HMDB01049)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:48 -0700
HMDB ID HMDB01049
Secondary Accession Numbers None
Metabolite Identification
Common 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (Des-Gly)-Glutathione
  2. 3GC
  3. 5-L-Glutamyl-L-cysteine
  4. 5-L-Glutamylcysteine
  5. g-Glutamylcysteine
  6. g-L-Glutamyl-L-cysteine
  7. gamma-Glu-cys
  8. gamma-Glutamylcysteine
  9. gamma-L-Glutamyl-L-cysteine
  10. H-gamma-Glu-Cys-OH
  11. H-Glu(Cys-OH)-OH
  12. L-g-Glutamyl-L-cysteine
  13. L-gamma-Glutamyl-L-cysteine
  14. L-gamma-Glutamylcysteine
  15. N-(1-Carboxy-2-mercaptoethyl)-L-Glutamine
  16. N-L-gamma-Glutamyl-L-Cysteine
  17. XN-L-g-glutamyl-Glutamine
  18. XN-L-gamma-glutamyl-Glutamine
Chemical Formula C8H14N2O5S
Average Molecular Weight 250.272
Monoisotopic Molecular Weight 250.062342258
IUPAC Name (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid
Traditional IUPAC Name glu(-cys)
CAS Registry Number 636-58-8
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 Key RITKHVBHSGLULN-WHFBIAKZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
Substituents
  • Alkylthiol
  • Carboxamide Group
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Primary Aliphatic Amine (Alkylamine)
  • Secondary Carboxylic Acid Amide
  • Thiol (Sulfanyl Compound)
Direct Parent N-acyl-alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glutamate metabolism
  • Component of Glutathione metabolism
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.62 g/L ALOGPS
LogP -2.53 ALOGPS
LogP -3.8 ChemAxon
LogS -1.98 ALOGPS
pKa (strongest acidic) 1.91 ChemAxon
pKa (strongest basic) 9.24 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 129.72 A2 ChemAxon
Rotatable Bond Count 7 ChemAxon
Refractivity 56.31 ChemAxon
Polarizability 23.36 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum LC-ESI-QTOF (UPLC Q-Tof Premier, Waters)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Fibroblasts
  • Neuron
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Cysteine Metabolism SMP00013 map00270 Link_out
Glutamate Metabolism SMP00072 map00250 Link_out
Glutathione Metabolism SMP00015 map00480 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
25.0 +/- 8.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
Article_icon
1.9 +/- 0.5 uM Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
Article_icon
0.46+/-0.14 umol/mmol creatinine Adult (>18 years old) Not Specified Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB03408 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB003603
KNApSAcK ID Not Available
Chemspider ID 110467 Link_out
KEGG Compound ID C00669 Link_out
BioCyc ID L-GAMMA-GLUTAMYLCYSTEINE Link_out
BiGG ID 35655 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01049 Link_out
Metagene Link HMDB01049 Link_out
METLIN ID 5966 Link_out
PubChem Compound 123938 Link_out
PDB ID 3GC Link_out
ChEBI ID 17515 Link_out
References
Synthesis Reference Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
  12. 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 Link_out
  13. 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 Link_out
  14. 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 Link_out
  15. 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 Link_out
Enzymes
Name: Glutamate--cysteine ligase catalytic subunit
Reactions:
  • ATP + L-glutamate + L-cysteine = ADP + phosphate + gamma-L-glutamyl-L-cysteine [RN:R00894]
Gene Name: GCLC
Uniprot ID: P48506 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutaminyl-peptide cyclotransferase
Reactions:
  • L-glutaminyl-peptide = 5-oxoprolyl-peptide + NH3 [RN:R04058]
Gene Name: QPCT
Uniprot ID: Q16769 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glutathione synthetase
Reactions:
  • ATP + gamma-L-glutamyl-L-cysteine + glycine = ADP + phosphate + glutathione [RN:R00497]
Gene Name: GSS
Uniprot ID: P48637 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-glutamylcyclotransferase
Reactions:
  • (gamma-L-glutamyl)-L-amino acid = 5-oxoproline + L-amino acid [RN:R03749]
Gene Name: GGCT
Uniprot ID: O75223 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA