Basic information
- CAS
57564-91-7- Standard SMILES
N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)C(=O)O- InChIKey
HYHSBSXUHZOYLX-WDSKDSINSA-N- Molecular formula
- C10H16N4O7S
- Average molar mass
- 336.32 g/mol
- Monoisotopic mass
- 336.07396985
Overview
S-nitrosoglutathione is a glutathione derivative that is glutathione in which the hydrogen attached to the sulfur has been replaced by a nitroso group. It has a role as a bronchodilator agent, a platelet aggregation inhibitor, a nitric oxide donor and a signalling molecule. It is a nitrosothio compound and a glutathione derivative. It is a conjugate acid of a S-nitrosoglutathione(2-).
Names & identifiers
- Preferred name
- S-Nitrosoglutathione
- IUPAC
- (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
- English name
- S-NITROSOGLUTATHIONE
- Molecular formula
- C10H16N4O7S
- Molecular weight
- 336.32
Names & synonyms
57564-91-7gsnoS-nitrosoglutathioneNitrosoglutathioneSNOGGlutathione thionitriteN-(N-L-gamma-Glutamyl-S-nitroso-L-cysteinyl)glycine78RRI89ZTODTXSID1040613Glycine, N-(N-L-gamma-glutamyl-S-nitroso-L-cysteinyl)-RVC 588 (PEPTIDE)(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid
Show more names
GNSORVC 588GSNO, SNOGS-NitrosoglutationeS-Nitrosylglutathione
CHEBI:50091(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acidS-Nitroso-GSH(2S)-2-amino-4-(((1R)-1-((carboxymethyl)carbamoyl)-2-(nitrososulfanyl)ethyl)carbamoyl)butanoic acid(2S)-2-amino-5-(((2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl)amino)-5-oxopentanoic acidRefChem:180705DTXCID401526730637-341-5
Database identifiers
- CAS
57564-91-7
Properties
Computed structural properties
- XLogP
- -4.8
- Topological polar surface area
- 214 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 10
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 445
Experimental & physicochemical properties
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 170 °C · >170°C (dec.)
- Density
- 1.68 · 1.68
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly), Water (Slightly)
- form
- Pink solid
- pka
- 2.21 · 2.21±0.10(Predicted)
- color
- Off-White to Pink
- Water Solubility
- 100 mM · Soluble to 100 mM in water
- Stability
- Hygroscopic
- InChI
- InChI=1/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-/s3
- InChIKey
- HYHSBSXUHZOYLX-FJGCHTOXNA-N
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- MC0558000
- risk_code
- 36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H311-H331
- Precautionary statements
- P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection.
Agents that cause an increase in the expansion of a bronchus or bronchial tubes.
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Drugs used to cause dilation of the blood vessels.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81)
Applications
DescriptionS-Nitroso-L-glutathione is an S-nitrosothiol NO donor based on naturally-occurring glutathione. It is a potent smooth muscle relaxant and inhibitor of platelet aggregation. Its stability in solution varies from seconds to hours depending on temperature, buffer composition, and metal content.
UsesA carrier of nitric oxide, relaxing smooth muscle and inhibiting platelet activation
UsesS-Nitrosoglutathione (GSNO) has been used:as a standard in reversed phase chromatography coupled to chemical vapour generation and atomic fluorescence detector (RPC-CVGAFS) and reversed phase chromatography fluorimetric (RPC-FD).as a standard in spectrophotometric and high-performance liquid chromatography (HPLC) assay.
General DescriptionA utility carrier of nitric oxide. Breaks down at physiological pH to produce nitric oxide. Causes smooth muscle relaxation and inhibits platelet aggregation. Induces apoptosis in mouse thymocytes. Note: 1 set = 5 x 2.5 mg.
Related reactions
26 records
Compound notes
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