Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:29:14 UTC |
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Update date | 2015-07-21 06:57:41 UTC |
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Primary ID | FDB023390 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | S-Nitrosoglutathione |
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Description | S-Nitrosoglutathione is a S-nitrosothiol. S-nitrosothiols (RSNOs) are thought to represent a circulating endogenous reservoir of nitric oxide (NO), and may have potential as donors of nitric oxide, distinct from currently used agents. They have the general formula RSNO, and naturally occurring examples include S-nitrosocysteine, S-nitrosoglutathione and S-nitrosoalbumin, in which R is an amino acid, polypeptide and protein respectively. RSNOs have anti-platelet properties, a theoretical role in the treatment of asthma and the potential to be used as agents to treat infectious diseases ranging from the common cold to AIDS. RSNOs are relatively unstable, being degraded to release nitric oxide and the corresponding disulphide. Their stability is influenced by the properties of the R group, heat, light, the presence of transition metal ions (in particular copper) and the presence of other thiols. RSNOs participate in transnitrosation reactions in which the -nitric oxide group is transferred to another thiol to form a more stable RSNO. Potential interactions of RSNOs include that with ascorbic acid (vitamin C), which enhances the ability of copper to catalyse their degradation. Transnitrosation reactions with thiol-containing enzymes can influence protein function, and the intracellular thiol glutathione, levels of which are influenced by many disease states, can also influence stability.
Genetic and biochemical data demonstrate a pivotal role for S-nitrosothiols in mediating the actions of nitric oxide synthases (NOSs). RSNOs serve to convey NO bioactivity and to regulate protein function. S-Nitrosoglutathione breakdown is subject to precise regulation. For example, S-Nitrosoglutathione reductase (GSNOR) breaks down cytosolic S-Nitrosoglutathione, ultimately to oxidized GSH and ammonia. GSNOR, in turn, modulates the levels of some S-nitrosylated proteins.
S-nitrosoglutathione, formed as nitric oxide moves away from erythrocytes in response to hemoglobin desaturation, may signal hypoxia-inducible factor-1-mediated physiologic and gene regulatory events in pulmonary endothelial cells without profound hypoxia, through a thiol-based reaction. S-Nitrosoglutathione stabilizes the alpha-subunit of hypoxia inducible factor1 (HIF-1) in normoxic cells, but not in the presence of PI3K inhibitors. (PMID: 11749666, 17541013, 16528016) [HMDB] |
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CAS Number | 57564-91-7 |
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Structure | |
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Synonyms | |
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Predicted Properties | |
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Chemical Formula | C10H16N4O7S |
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IUPAC name | (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid |
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InChI Identifier | InChI=1S/C10H16N4O7S/c11-5(10(19)20)1-2-7(15)13-6(4-22-14-21)9(18)12-3-8(16)17/h5-6H,1-4,11H2,(H,12,18)(H,13,15)(H,16,17)(H,19,20)/t5-,6-/m0/s1 |
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InChI Key | HYHSBSXUHZOYLX-WDSKDSINSA-N |
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Isomeric SMILES | N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O |
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Average Molecular Weight | 336.322 |
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Monoisotopic Molecular Weight | 336.073969576 |
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Classification |
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Description | Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. |
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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 | Peptides |
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Alternative Parents | |
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Substituents | - Alpha peptide
- N-acyl-alpha-amino acid
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid
- Alpha-amino acid or derivatives
- L-alpha-amino acid
- Dicarboxylic acid or derivatives
- Fatty acid
- Organic s-nitroso compound
- Amino acid or derivatives
- Amino acid
- Nitrosothiol
- Nitrosothiol-group
- Organic nitroso compound
- Carboximidic acid
- Carboximidic acid derivative
- Carboxylic acid
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Sulfenyl compound
- Hydrocarbon derivative
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Amine
- Organic nitrogen compound
- Organic oxygen compound
- Carbonyl group
- 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 | |
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Ontology |
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Disposition | Biological location: Source: |
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Physico-Chemical Properties |
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Physico-Chemical Properties - Experimental | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | S-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0006-7492000000-b8047614ec6fd11afa64 | Spectrum | Predicted GC-MS | S-Nitrosoglutathione, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00rl-9221500000-4b61aaeb02d9e9a1ce8f | Spectrum | Predicted GC-MS | S-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | S-Nitrosoglutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-05mx-2195000000-a563223d38cc871e075e | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a7i-5690000000-602911e49e2773fc604a | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4i-6910000000-ec94284144a3d795c058 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00kr-1069000000-64cab5a8bb487605b5dd | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-07p0-5494000000-a77a2e8025c498cc7bd4 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-022c-9400000000-3a9e24cebbb82d680c46 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4r-0139000000-a465a5f3cb9aeab17961 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fr-0961000000-b3a2bbbe2a8374ddba48 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-001i-9700000000-7c8a8435959ceff23bf0 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0fe0-0469000000-67ad5cd47cd93ab5f965 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03di-9721000000-069b0ee7c891f9f28469 | 2021-09-22 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-03di-9400000000-5343c1d557eb50ff2bb5 | 2021-09-22 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 94647 |
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ChEMBL ID | CHEMBL63507 |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 104858 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB04645 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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