S-Nitrosoglutathione

HCID 104858CAS 57564-91-7

Grundinformationen

Standard-SMILES
N[C@@H](CCC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)C(=O)O
InChIKey
HYHSBSXUHZOYLX-WDSKDSINSA-N
Summenformel
C10H16N4O7S
Durchschnittliche Molmasse
336,32 g/mol
Monoisotopische Masse
336,07396985

Überblick

S-nitrosoglutathione is a glutathione derivative that is glutathione in which the hydrogen attached to the sulfur has been replaced by a nitroso group.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-).

Namen und Bezeichner

Bevorzugter Name
S-Nitrosoglutathione
IUPAC
(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-3-nitrososulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Englischer Name
S-NITROSOGLUTATHIONE
Summenformel
C10H16N4O7S
Molmasse
336.32

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

CAS
57564-91-7
PubChem CID
104858
DTXSID
DTXSID1040613
ChEMBL
CHEMBL63507
ChEBI
CHEBI:50091
UNII
78RRI89ZTO
EC Number
637-341-5
Nikkaji
J361.904D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-4,8
Polarare Oberfläche (TPSA)
214 Ų
H-Brücken-Donoren
5
H-Brücken-Akzeptoren
10
Frei drehbare Bindungen
10
Schwere Atome
22

Experimentelle und physikochemische Eigenschaften

Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
170 °C · >170°C (dec.)
Dichte
1.68 · 1.68
Brechungsindex
1.6 · 1.6000 (estimate)
storage temp.
-20 °C · -20°C
Löslichkeit
DMSO (Slightly), Water (Slightly)
Aggregatzustand
Pink solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheitsdaten

wgk
3
RTECS-Nr.
MC0558000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36
Speicherklasse
11 - Combustible Solids

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 6 Einträge

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)

Anwendungen · 2 Einträge

BeschreibungS-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.

VerwendenS-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.

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