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S-nitrosoglutathione is a glutathione derivative that is glutathione in which the hydrogen attached to the sulfur has been replaced by a nitroso group.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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 445
Experimentelle und physikochemische Eigenschaften
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
- pka
- 2.21 · 2.21±0.10(Predicted)
- Farbe
- Off-White to Pink
- Wasserlöslichkeit
- 100 mM · Soluble to 100 mM in water
- Stabilität
- 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
- SMILES
- [C@@H](CSN=O)(NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O |&1:0,10,r|
- CAS Datenbank
- 57564 · 57564-91-7(CAS DataBase Reference)
Sicherheit und Regulatorisches
GHS-Klassifizierung
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.
Gefahrenhinweise
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
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
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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