1.0 2011-09-21 00:29:14 UTC 2025-11-19 02:43:57 UTC FDB023390 S-Nitrosoglutathione 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] Glutathione thionitrite GSNO N-(N-L-g-Glutamyl-S-nitroso-L-cysteinyl)glycine n-(n-l-gamma-glutamyl-s-nitroso-l-cysteinyl)glycine N-(N-L-γ-glutamyl-S-nitroso-L-cysteinyl)glycine Nitrosoglutathione SNOG C10H16N4O7S 336.322 336.073969576 (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid nitrosoglutathione 57564-91-7 N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O 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 HYHSBSXUHZOYLX-WDSKDSINSA-N 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. Peptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidic acids Carboxylic acids Dicarboxylic acids and derivatives Fatty acids and conjugates Hydrocarbon derivatives L-alpha-amino acids Monoalkylamines N-acyl-alpha amino acids Nitrosothiols Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Sulfenyl compounds Aliphatic acyclic compound Alpha peptide Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Carbonyl group Carboximidic acid Carboximidic acid derivative Carboxylic acid Dicarboxylic acid or derivatives Fatty acid Hydrocarbon derivative L-alpha-amino acid N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid Nitrosothiol Nitrosothiol-group Organic 1,3-dipolar compound Organic nitrogen compound Organic nitroso compound Organic oxide Organic oxygen compound Organic s-nitroso compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound Sulfenyl compound glutathione derivative Solid logp -2.97 ALOGPS logs -2.29 ALOGPS solubility 1.73e+00 g/l ALOGPS logp -4.7 ChemAxon pka_strongest_acidic 1.6 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid ChemAxon average_mass 336.322 ChemAxon mono_mass 336.073969576 ChemAxon smiles N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(O)=O)C(O)=O ChemAxon formula C10H16N4O7S ChemAxon inchi 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 ChemAxon inchikey HYHSBSXUHZOYLX-WDSKDSINSA-N ChemAxon polar_surface_area 188.25 ChemAxon refractivity 74.48 ChemAxon polarizability 30.77 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 9 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 18108 Specdb::CMs 38777 Specdb::CMs 134055 Specdb::CMs 141789 Specdb::NmrOneD 149900 Specdb::NmrOneD 149901 Specdb::NmrOneD 149902 Specdb::NmrOneD 149903 Specdb::NmrOneD 149904 Specdb::NmrOneD 149905 Specdb::NmrOneD 149906 Specdb::NmrOneD 149907 Specdb::NmrOneD 149908 Specdb::NmrOneD 149909 Specdb::NmrOneD 149910 Specdb::NmrOneD 149911 Specdb::NmrOneD 149912 Specdb::NmrOneD 149913 Specdb::NmrOneD 149914 Specdb::NmrOneD 149915 Specdb::NmrOneD 149916 Specdb::NmrOneD 149917 Specdb::NmrOneD 149918 Specdb::NmrOneD 149919 Specdb::MsMs 306127 Specdb::MsMs 306128 Specdb::MsMs 306129 Specdb::MsMs 349672 Specdb::MsMs 349673 Specdb::MsMs 349674 Specdb::MsMs 2389154 Specdb::MsMs 2389155 Specdb::MsMs 2389156 Specdb::MsMs 2573111 Specdb::MsMs 2573112 Specdb::MsMs 2573113 HMDB04645 #<Reference:0x000055ce31a98508> #<Reference:0x000055ce31a98350> #<Reference:0x000055ce31a98198> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823