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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-02-26 21:22:53 UTC |
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HMDB ID | HMDB0001049 |
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Secondary Accession Numbers | - HMDB0029146
- HMDB01049
- HMDB29146
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Metabolite Identification |
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Common Name | gamma-Glutamylcysteine |
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Description | gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-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 the glutamate metabolism pathway (KEGG). |
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Structure | |
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Synonyms | Value | Source |
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γ-Glu-Cys | HMDB, Generator | γ-L-Glu-L-Cys | HMDB | γ-Glutamylcysteine | HMDB, Generator | γ-L-Glutamyl-L-cysteine | HMDB, Generator | L-γ-Glutamyl-L-cysteine | HMDB | N-γ-Glutamylcysteine | HMDB | N-L-γ-Glutamylcysteine | HMDB | N-L-γ-Glutamyl-L-cysteine | HMDB | gamma-Glu-Cys | HMDB, ChEBI | gamma-L-Glu-L-Cys | HMDB | gamma-L-Glutamyl-L-cysteine | HMDB, ChEBI | L-gamma-Glutamyl-L-cysteine | HMDB | N-gamma-Glutamylcysteine | HMDB | N-L-gamma-Glutamylcysteine | HMDB | N-L-gamma-Glutamyl-L-cysteine | HMDB | gamma-Glutamylcysteine | HMDB | 5-L-Glutamyl-L-cysteine | ChEBI | L-gamma-Glutamylcysteine | ChEBI | g-Glutamylcysteine | Generator | g-Glu-Cys | Generator | g-L-Glutamyl-L-cysteine | Generator | L-g-Glutamylcysteine | Generator | L-γ-glutamylcysteine | Generator | 5-L-Glutamylcysteine | HMDB | H-gamma-Glu-Cys-OH | HMDB | L-g-Glutamyl-L-cysteine | HMDB | N-γ-L-Glutamyl-L-cysteine | HMDB |
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Chemical Formula | C8H14N2O5S |
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Average Molecular Weight | 250.272 |
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Monoisotopic Molecular Weight | 250.062342258 |
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IUPAC Name | (2S)-2-amino-4-{[(1R)-1-carboxy-2-sulfanylethyl]carbamoyl}butanoic acid |
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Traditional Name | gamma-glutamylcysteine |
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CAS Registry Number | 636-58-8 |
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SMILES | N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O |
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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 |
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InChI Key | RITKHVBHSGLULN-WHFBIAKZSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | N-acyl-alpha amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-054t-1920100000-5ce9a082971db6d9e2e9 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-054t-1920100000-5ce9a082971db6d9e2e9 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-053u-9630000000-344be03dbe2132b00c88 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-00b9-8494000000-88b1eea1e1badaee084b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0udi-0090000000-50bd1555ededc1afde80 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0290000000-385ca433f03af7530f47 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0ue9-5490000000-95d45a9cd2bb6249d3a2 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-001i-9510000000-5f29ca903abe05256c83 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-001i-9510000000-5f29ca903abe05256c83 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000t-1390000000-e723899e4ca71bda7600 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00sj-3960000000-9a2f96ad7d24e7546315 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00e9-9300000000-e14b428bbb5b63d3ae06 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05fr-1790000000-2aaa1344429a2297cc6b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-4920000000-4ad42780853d5599c05b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-9400000000-b67fd0eaf646aa8f47b3 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | - Fibroblasts
- Neuron
- Placenta
- Prostate
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 3.05 +/- 0.11 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 25.0 +/- 8.0 uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 1.9 +/- 0.5 uM | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Normal | | details | Urine | Detected and Quantified | 0.46+/-0.14 umol/mmol creatinine | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 2.07 +/- 0.12 uM | Adult (>18 years old) | Both | Schizophrenia | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Both | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Both | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Ulcerative colitis | | details | Feces | Detected but not Quantified | Not Quantified | Children (6 - 18 years old) | Not Specified | Unclassified IBD | | details |
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Associated Disorders and Diseases |
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Disease References | Schizophrenia |
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- Fukushima T, Iizuka H, Yokota A, Suzuki T, Ohno C, Kono Y, Nishikiori M, Seki A, Ichiba H, Watanabe Y, Hongo S, Utsunomiya M, Nakatani M, Sadamoto K, Yoshio T: Quantitative analyses of schizophrenia-associated metabolites in serum: serum D-lactate levels are negatively correlated with gamma-glutamylcysteine in medicated schizophrenia patients. PLoS One. 2014 Jul 8;9(7):e101652. doi: 10.1371/journal.pone.0101652. eCollection 2014. [PubMed:25004141 ]
| Crohn's disease |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
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- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB03408 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB003603 |
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KNApSAcK ID | C00007507 |
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Chemspider ID | 110467 |
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KEGG Compound ID | C00669 |
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BioCyc ID | L-GAMMA-GLUTAMYLCYSTEINE |
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BiGG ID | 35655 |
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Wikipedia Link | Gamma-Glutamylcysteine |
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METLIN ID | 5966 |
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PubChem Compound | 123938 |
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PDB ID | Not Available |
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ChEBI ID | 17515 |
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Food Biomarker Ontology | Not Available |
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VMH ID | GLUCYS |
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MarkerDB ID | |
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References |
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Synthesis Reference | Bridge, Wallace John; Zarka, Martin Hani. Enzymic production of g-glutamylcysteine. PCT Int. Appl. (2006), 76pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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