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| Identification |
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| YMDB ID | YMDB00057 |
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| Name | Oxidized glutathione |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Glutathione (GSH) is a tripeptide that contains an unusual peptide linkage between the amine group of cysteine and the carboxyl group of the glutamate side-chain. It is an antioxidant and a coenzyme in various enzymatic reactions. Glutathione exists in reduced (GSH) and oxidized (GSSG) states. Glutathione is found almost exclusively in its reduced form, since the enzyme that reverts it from its oxidized form, glutathione reductase, is constitutively active and inducible upon oxidative stress. |
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| Structure | |
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| Synonyms | - (2S)-2-Azaniumyl-4-{[(1R)-2-{[(2R)-2-[(4S)-4-azaniumyl-4-carboxylatobutanamido]-2-[(carboxylatomethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxylatomethyl)carbamoyl]ethyl]carbamoyl}butanoate
- glutathione
- Glutathione disulfide
- glutathione disulphide
- glutathione ox
- glutathione oxidized
- GSH
- GSSG
- l-glutathione oxidized
- L(-)-Glutathione(oxidized)
- oxidised glutathione
- Oxidized glutathione
- OXIDIZED GLUTATHIONE DISULFIDE
- OXIDIZED-GLUTATHIONE
- Oxiglutatione
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| CAS number | 27025-41-8 |
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| Weight | Average: 612.631
Monoisotopic: 612.151961898 |
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| InChI Key | YPZRWBKMTBYPTK-UHFFFAOYSA-N |
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| InChI | InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38) |
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| IUPAC Name | 2-amino-4-[(2-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]disulfanyl}-1-[(carboxymethyl)carbamoyl]ethyl)carbamoyl]butanoic acid |
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| Traditional IUPAC Name | oxiglutatione |
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| Chemical Formula | C20H32N6O12S2 |
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| SMILES | [H]OC(=O)C([H])([H])N([H])C(=O)C([H])(N([H])C(=O)C([H])([H])C([H])([H])C([H])(N([H])[H])C(=O)O[H])C([H])([H])SSC([H])([H])C([H])(N([H])C(=O)C([H])([H])C([H])([H])C([H])(N([H])[H])C(=O)O[H])C(=O)N([H])C([H])([H])C(=O)O[H] |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
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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 | Oligopeptides |
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| Alternative Parents | |
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| Substituents | - Alpha-oligopeptide
- Gamma-glutamyl alpha peptide
- Glutamine or derivatives
- N-acyl-alpha-amino acid
- Tetracarboxylic acid or derivatives
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- Cysteine or derivatives
- Alpha-amino acid
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Fatty amide
- N-acyl-amine
- Fatty acyl
- Amino acid or derivatives
- Carboxamide group
- Amino acid
- Dialkyldisulfide
- Secondary carboxylic acid amide
- Organic disulfide
- Sulfenyl compound
- Carboxylic acid
- Organopnictogen compound
- Primary aliphatic amine
- Hydrocarbon derivative
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- Organic oxide
- Amine
- Organonitrogen compound
- Organooxygen compound
- Organosulfur compound
- Primary amine
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | Not Available |
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| Physical Properties |
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| State | Solid |
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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | - extracellular
- mitochondrion
- cytoplasm
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | |
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| KEGG Pathways | |
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| SMPDB Reactions | Not Available |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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| 94 ± 4 µM | YPD medium/SC medium | aerobic | Baker's yeast | PMID: 15277542 | | Conversion Details Here |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0900000000-c8147955c6b355f0fc5c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0a4i-0910000000-3e6195d480fbfe87b449 | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-02t9-2121090000-ae2cd04146f2eea049a5 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01q3-2111039000-a2c6d786111b549344fe | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0uki-0290000000-04456f914411a2ecbe4f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0a4i-0039210000-772eee67ad10a2d98fa7 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-08fr-1957008000-f8812fd72d475ecd2693 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0000109000-65d563bcfc551b4a7abd | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-03di-0003309000-7555effd0b74737b9d2f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0a4i-0259201000-2cd328143ce713c285d9 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-05d0-0493000000-93bd088394049a484b9d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-001r-0190000000-88b871b5a3f668f4b3a1 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-0a59-0019811000-b24651cf6fc55de750b8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-053s-0495300000-69ab8e397b7a546ecd3f | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-053r-0007920000-39da34018ceb610daa32 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0000009000-9cde769e8905f413f7e3 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0000009000-4e3c9569882ab5507bf2 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-02na-2011492000-e5bf21a4b84acc1cf18f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-9002540000-c313b0aedf04e56ccf77 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-9012110000-27ec93f3d13ce2136a4f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0147096000-d734e389344c1dc9b900 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0lxx-1597071000-aba0237f549185706415 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0007-9501140000-204a269186f92e44ac10 | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer |
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| References |
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| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Muller, E. G. (1996). "A glutathione reductase mutant of yeast accumulates high levels of oxidized glutathione and requires thioredoxin for growth." Mol Biol Cell 7:1805-1813.8930901
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Outten, C. E., Culotta, V. C. (2004). "Alternative start sites in the Saccharomyces cerevisiae GLR1 gene are responsible for mitochondrial and cytosolic isoforms of glutathione reductase." J Biol Chem 279:7785-7791.14672937
- Ostergaard, H., Tachibana, C., Winther, J. R. (2004). "Monitoring disulfide bond formation in the eukaryotic cytosol." J Cell Biol 166:337-345.15277542
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| Synthesis Reference: | Saito, Susumu; Nishijima, Kunihide; Kataoka, Katsuyuki; Aoyanagi, Yoshinori; Fukuda, Yoji; Ito, Homare. Manufacture of oxidized glutathione from reduced glutathione with ascorbic acid and ascorbate oxidase. Jpn. Kokai Tokkyo Koho (1995), 4 pp. |
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| External Links: | |
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