(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid

• ChemBase ID: 133964
• Molecular Formular: C10H16N4O7S
• Molecular Mass: 336.32164
• Monoisotopic Mass: 336.07396987
• SMILES: C(CC(=O)N[C@@H](CSN=O)C(=O)NCC(=O)O)[C@@H](C(=O)O)N
• Canonical SMILES: O=NSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N
• 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
• InChIKey: HYHSBSXUHZOYLX-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-(nitrososulfanyl)ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: nitrosoglutathione
• Synonyms: GSNO; SNOG; S-Nitrosoglutathione; L-γ-Glutamyl-S-nitroso-L-cysteinyl-glycine; GNSO; RVC 588; S-Nitroso-L-glutathione

Database IDs

• CAS Number: 57564-91-7
• MDL Number: MFCD00214341
• PubChem SID: 162228241; 24278587
• PubChem CID: 104858

CALCULATED PROPERTIES

• Acid pKa: 1.6027608
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -6.7549415
• LogD (pH = 7.4): -7.9891505
• Log P: -4.687954
• Molar Refractivity: 74.4843 cm^3
• Polarizability: 28.737278 Å^3
• Polar Surface Area: 188.25 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Pink Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: MC0558000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%

DETAILS

Sigma Aldrich - N4148

Biochem/physiol Actions
NO donor in vivo, smooth muscle relaxant, vasodilator, inhibits platelet activation.

Toronto Research Chemicals - N527500

A carrier of nitric oxide, relaxing smooth muscle and inhibiting platelet activation.

REFERENCES

• Thompson, C., et al.: Toxicol., App. Pharmacol., 233, 355 (2008)
• Bateman, R., et al.: J. Biol. Chem., 283, 35756 (2008)
• Foster, M., et al.: Biochem., 48, 792 (2008)