2-acetamido-3-methyl-3-(nitrososulfanyl)butanoic acid

• ChemBase ID: 133176
• Molecular Formular: C7H12N2O4S
• Molecular Mass: 220.24618
• Monoisotopic Mass: 220.05177787
• SMILES: CC(=O)NC(C(=O)O)C(C)(C)SN=O
• Canonical SMILES: O=NSC(C(C(=O)O)NC(=O)C)(C)C
• InChI: InChI=1S/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)
• InChIKey: ZIIQCSMRQKCOCT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-acetamido-3-methyl-3-(nitrososulfanyl)butanoic acid
• IUPAC Traditional name: 2-acetamido-3-methyl-3-(nitrososulfanyl)butanoic acid
• Synonyms: N-Acetyl-3-(nitrosothio)-DL-valine; S-Nitroso-N-acetylpenicillamine; SNAP; S-Nitroso-N-acetyl-DL-penicillamine; N-(Acetyloxy)-3-(nitrosothio)valine; S-Nitroso-N-acetyl-D,L-penicillamine

Database IDs

• CAS Number: 67776-06-1; 152971-80-7
• MDL Number: MFCD00272624
• PubChem SID: 162227453; 24278584
• PubChem CID: 5231

CALCULATED PROPERTIES

• Acid pKa: 3.3565793
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.7327143
• LogD (pH = 7.4): -3.0171466
• Log P: 0.39634806
• Molar Refractivity: 51.9278 cm^3
• Polarizability: 19.724411 Å^3
• Polar Surface Area: 95.83 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥20 mg/mL, clear, light green; H2O: ≥2 mg/mL
• Apperance: Green Crystalline Solid; green powder
• Melting Point: 152-154°C dec.

Safety Information

• Storage Condition: -20°C Freezer
• 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%
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - N3398

Biochem/physiol Actions
NO donor; vasodilator, smooth muscle relaxant, lymphocyte activator. Activates soluble guanylyl cyclase.
SNAP, a nitrosothiol derivative, releases nitric oxide (NO.) under physiological conditions thus making it a useful tool for studying pharmacological and physiological actions of NO. Because of its NO releasing properties SNAP is a potent vasodilator in vitro and in vivo and is less prone to produce pharmacological tolerance.

Toronto Research Chemicals - N522500

Produced concentration-related relaxations of mouse anococcygeus, in a range similar to that already found for NO and other nitrovasodilators. A potent relaxant of non-vascular smooth muscle. Serves as an NO donor.

REFERENCES

• Bauer & Fung: J. Pharmacol. Exp. Ther., 256, 249 (1991)
• Gibson, A., et al.: Brit. J. Pharm., 107, 715 (1991)
• Shaffer, et al.: J. Pharm. Exper. Ther., 260, 286 (1991)
• Jansen, A., et al.: J. Pharmacol. Exp. Ther., 261, 154 (1991)
• Lander, H.M. et al.: J.