3-methyl-3-(nitrososulfanyl)-2-propanamidobutanoic acid

• ChemBase ID: 175510
• Molecular Formular: C8H14N2O4S
• Molecular Mass: 234.27276
• Monoisotopic Mass: 234.06742794
• SMILES: S(C(C(NC(=O)CC)C(=O)O)(C)C)N=O
• Canonical SMILES: CCC(=O)NC(C(SN=O)(C)C)C(=O)O
• InChI: InChI=1S/C8H14N2O4S/c1-4-5(11)9-6(7(12)13)8(2,3)15-10-14/h6H,4H2,1-3H3,(H,9,11)(H,12,13)
• InChIKey: XRIWLEWQNCECEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-3-(nitrososulfanyl)-2-propanamidobutanoic acid
• IUPAC Traditional name: 3-methyl-3-(nitrososulfanyl)-2-propanamidobutanoic acid
• Synonyms: SNPP; 3-(Nitrosothio)-N-(1-oxopropyl)valine; S-Nitroso-N-propionyl-D,L-penicillamine

Database IDs

• CAS Number: 225233-98-7
• PubChem SID: 164231420
• PubChem CID: 5057842

CALCULATED PROPERTIES

• Acid pKa: 3.4663975
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.92710847
• LogD (pH = 7.4): -2.2882783
• Log P: 1.0968839
• Molar Refractivity: 56.5547 cm^3
• Polarizability: 21.536701 Å^3
• Polar Surface Area: 95.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Green Crystalline Solid

DETAILS

Toronto Research Chemicals - N545710

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.