Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C8H14N2O5S |
| Molecular Weight | 250.272 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCC(=O)N[C@@H](CS)C(O)=O)C(O)=O
InChI
InChIKey=RITKHVBHSGLULN-WHFBIAKZSA-N
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
| Molecular Formula | C8H14N2O5S |
| Molecular Weight | 250.272 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular mechanism of transforming growth factor (TGF)-beta1-induced glutathione depletion in alveolar epithelial cells. Involvement of AP-1/ARE and Fra-1. | 2002-06-14 |
|
| Glutathione and K(+) channel remodeling in postinfarction rat heart. | 2002-06 |
|
| Bleomycin upregulates expression of gamma-glutamylcysteine synthetase in pulmonary artery endothelial cells. | 2002-06 |
|
| Reversal of cisplatin resistance in human ovarian cancer cell lines by a c-jun antisense oligodeoxynucleotide (ISIS 10582): evidence for the role of transcription factor overexpression in determining resistant phenotype. | 2002-05-01 |
|
| Determination of glutamate-cysteine ligase (gamma-glutamylcysteine synthetase) activity by high-performance liquid chromatography and electrochemical detection. | 2002-05-01 |
|
| Glutathione synthetase from Plasmodium falciparum. | 2002-05-01 |
|
| Effect of ursodeoxycholic acid on methionine adenosyltransferase activity and hepatic glutathione metabolism in rats. | 2002-05 |
|
| Redox-sensitive interaction between KIAA0132 and Nrf2 mediates indomethacin-induced expression of gamma-glutamylcysteine synthetase. | 2002-04-01 |
|
| Isothiocyanates: mechanism of cancer chemopreventive action. | 2002-04 |
|
| Oxidant stress induces gamma-glutamylcysteine synthetase and glutathione synthesis in human bronchial epithelial NCI-H292 cells. | 2002-04 |
|
| Carboplatin AUC and gamma-glutamylcysteine synthetase gene expression in peripheral mononuclear cells of lung cancer patients. | 2002-03-26 |
|
| Increased rate of glutathione synthesis from cystine in drug-resistant MCF-7 cells. | 2002-03-01 |
|
| Flavonoids increase the intracellular glutathione level by transactivation of the gamma-glutamylcysteine synthetase catalytical subunit promoter. | 2002-03-01 |
|
| Study of Cd2+ complexation by the glutathione fragments Cys-Gly (CG) and gamma-Glu-Cys (gamma-EC) by differential pulse polarography. | 2002-03 |
|
| Overexpression of the putative thiol conjugate transporter TbMRPA causes melarsoprol resistance in Trypanosoma brucei. | 2002-03 |
|
| Induction of tolerance to naphthalene in Clara cells is dependent on a stable phenotypic adaptation favoring maintenance of the glutathione pool. | 2002-03 |
|
| Characterization of non-small-cell lung cancer cell lines established before and after chemotherapy. | 2002-03 |
|
| Genetic determinants of lung cancer short-term survival: the role of glutathione-related genes. | 2002-03 |
|
| Redox regulation of TNF-alpha biosynthesis: augmentation by irreversible inhibition of gamma-glutamylcysteine synthetase and the involvement of an IkappaB-alpha/NF-kappaB-independent pathway in alveolar epithelial cells. | 2002-03 |
|
| Determination of intracellular glutathione and thiols by high performance liquid chromatography with a gold electrode at the femtomole level: comparison with a spectroscopic assay. | 2002-02-15 |
|
| Modulation of DNA single-strand breaks by intracellular glutathione in human lung cells exposed to asbestos fibers. | 2002-02-15 |
|
| Cellular zinc sensors: MTF-1 regulation of gene expression. | 2002-02-08 |
|
| Induction of multidrug resistance proteins MRP1 and MRP3 and gamma-glutamylcysteine synthetase gene expression by nonsteroidal anti-inflammatory drugs in human colon cancer cells. | 2002-02-08 |
|
| Redox signaling-mediated regulation of lipopolysaccharide-induced proinflammatory cytokine biosynthesis in alveolar epithelial cells. | 2002-02 |
|
| Antioxidant defense mechanisms in human neutrophils. | 2002-02 |
|
| Antioxidant enzyme activities and mitochondrial fatty acids in pulmonary hypertension syndrome (PHS) in broilers. | 2002-02 |
|
| Glucose-induced oxidative stress in mesangial cells. | 2002-02 |
|
| The adaptive response of Saccharomyces cerevisiae to mercury exposure. | 2002-02 |
|
| Acrylamide-induced cellular transformation. | 2002-02 |
|
| Escherichia coli B gamma-glutamylcysteine synthetase: modification, purification, crystallization and preliminary crystallographic analysis. | 2002-02 |
|
| The involvement of L-gamma-glutamyl-L-cysteinyl-glycine (glutathione/GSH) in the mechanism of redox signaling mediating MAPK(p38)-dependent regulation of pro-inflammatory cytokine production. | 2002-01-15 |
|
| Increased sensitivity of homozygous Sod2 mutant mice to oxygen toxicity. | 2002-01-15 |
|
| L-Buthionine-(S,R)-sulfoximine, an irreversible inhibitor of gamma-glutamylcysteine synthetase, augments LPS-mediated pro-inflammatory cytokine biosynthesis: evidence for the implication of an IkappaB-alpha/NF-kappaB insensitive pathway. | 2002-01-10 |
|
| Gonadotropin regulation of glutathione synthesis in the rat ovary. | 2002-01-10 |
|
| Expression of heavy subunit of gamma-glutamylcysteine synthetase (gamma-GCSh) in human colorectal carcinoma. | 2002-01-01 |
|
| The coffee components kahweol and cafestol induce gamma-glutamylcysteine synthetase, the rate limiting enzyme of chemoprotective glutathione synthesis, in several organs of the rat. | 2002-01 |
|
| Measurement of thiol-containing amino acids and phytochelatin (PC2) via capillary electrophoresis with laser-induced fluorescence detection. | 2002-01 |
|
| Interactions of algal ligands, metal complexation and availability, and cell responses of the diatom Ditylum brightwellii with a gradual increase in copper. | 2002-01 |
|
| Up-regulation of K(+) channels in diabetic rat ventricular myocytes by insulin and glutathione. | 2002-01 |
|
| Modulation of cell injury and survival by high glucose and advancing age. | 2001-12-15 |
|
| Na+ dependent glutamate transporters (EAAT1, EAAT2, and EAAT3) in primary astrocyte cultures: effect of oxidative stress. | 2001-12-13 |
|
| Expression of gamma-glutamyl cysteine synthetase in nonsmall cell lung carcinoma. | 2001-12-01 |
|
| [Gene expression profiling of human ovarian epithelial tumors by digo nucleotide microarray]. | 2001-12 |
|
| L-pyroglutamic acid inhibits energy production and lipid synthesis in cerebral cortex of young rats in vitro. | 2001-12 |
|
| Gamma-glutamyl transpeptidase and glutathione biosynthesis in non-tumorigenic and tumorigenic rat liver oval cell lines. | 2001-12 |
|
| Restoration of glutathione levels in vascular smooth muscle cells exposed to high glucose conditions. | 2001-11-15 |
|
| Role of reactive oxygen species and glutathione in inorganic mercury-induced injury in human glioma cells. | 2001-11 |
|
| Increasing the glutathione content in a chilling-sensitive maize genotype using safeners increased protection against chilling-induced injury. | 2001-11 |
|
| Rapid isolation of monoclonal antibodies. Monitoring enzymes in the phytochelatin synthesis pathway. | 2001-11 |
|
| Synthesis and stability of phytochelatins induced by cadmium and lead in the marine diatom Phaeodactylum tricornutum. | 2001-10 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:08:07 GMT 2025
by
admin
on
Mon Mar 31 19:08:07 GMT 2025
|
| Record UNII |
M984VJS48P
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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DTXSID90212978
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123938
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636-58-8
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DB03408
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GAMMA-GLUTAMYLCYSTEINE
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M984VJS48P
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17515
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