S-Nitrosoglutathione

S-Nitrosoglutathione
Names
	IUPAC name L-γ-Glutamyl-S-nitroso-L-cysteinylglycine
	Systematic IUPAC name (2S)-2-Amino-5-({(2R)-1-[(carboxymethyl)amino]-3-(nitrososulfanyl)-1-oxopropan-2-yl}amino)-5-oxopentanoic acid
	Other names Glutathione thionitrite; S-Nitroso-L-glutathione; SNOG; GSNO
Identifiers
CAS Number	57564-91-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3566211
ChEBI	CHEBI:50091 ;
ChEMBL	ChEMBL156747 ;
ChemSpider	94647 ;
ECHA InfoCard	100.165.055
MeSH	S-Nitrosoglutathione
PubChem CID	104858;
RTECS number	MC0558000;
UNII	78RRI89ZTO ;
CompTox Dashboard (EPA)	DTXSID1040613 ;
	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 Key: HYHSBSXUHZOYLX-WDSKDSINSA-N ;
	SMILES C(CC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)[C@@H](C(=O)O)N;
Properties
Chemical formula	C10H16N4O7S
Molar mass	336.32 g·mol−1
log P	−2.116
Acidity (pKa)	2.212
Basicity (pKb)	11.785
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

S-Nitrosoglutathione (GSNO) is an endogenous S-nitrosothiol (SNO) that plays a critical role in nitric oxide (NO) signaling and is a source of bioavailable NO. NO coexists in cells with SNOs that serve as endogenous NO carriers and donors. SNOs spontaneously release NO at different rates and can be powerful terminators of free radical chain propagation reactions, by reacting directly with ROO• radicals, yielding nitro derivatives as end products.^[1] NO is generated intracellularly by the nitric oxide synthase (NOS) family of enzymes: nNOS, eNOS and iNOS while the in vivo source of many of the SNOs is unknown. In oxygenated buffers, however, formation of SNOs is due to oxidation of NO to dinitrogen trioxide (N₂O₃).^[2] Some evidence suggests that both exogenous NO and endogenously derived NO from nitric oxide synthases can react with glutathione to form GSNO.

^ de Oliveira CP, de Lima VM, Simplicio FI, Soriano FG, de Mello ES, de Souza HP, Alves VA, Laurindo FR, Carrilho FJ, de Oliveira MG (April 2008). "Prevention and reversion of nonalcoholic steatohepatitis in OB/OB mice by S-nitroso-N-acetylcysteine treatment". J Am Coll Nutr. 27 (2): 299–305. doi:10.1080/07315724.2008.10719703. PMID 18689562. S2CID 29904719.
^ Giustarini D, Milzani A, Dalle-Donne I, Rossi R (May 2007). "Detection of S-nitrosothiols in biological fluids: a comparison among the most widely applied methodologies". J. Chromatogr. B. 851 (1–2): 124–39. doi:10.1016/j.jchromb.2006.09.031. PMID 17035104.

[pmid18689562-1] Oliveira CP, de Lima VM, Simplicio FI, Soriano FG, de Mello ES, de Souza HP, Alves VA, Laurindo FR, Carrilho FJ, de Oliveira MG (April 2008). "Prevention and reversion of nonalcoholic steatohepatitis in OB/OB mice by S-nitroso-N-acetylcysteine treatment". J Am Coll Nutr. 27 (2): 299–305. doi:10.1080/07315724.2008.10719703. PMID 18689562. S2CID 29904719.

[pmid17035104-2] Giustarini D, Milzani A, Dalle-Donne I, Rossi R (May 2007). "Detection of S-nitrosothiols in biological fluids: a comparison among the most widely applied methodologies". J. Chromatogr. B. 851 (1–2): 124–39. doi:10.1016/j.jchromb.2006.09.031. PMID 17035104.

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