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

• ChemBase ID: 175523
• Molecular Formular: C10H18N2O4S
• Molecular Mass: 262.32592
• Monoisotopic Mass: 262.09872807
• SMILES: N(C(=O)CCCC)C(C(SN=O)(C)C)C(=O)O
• Canonical SMILES: CCCCC(=O)NC(C(SN=O)(C)C)C(=O)O
• InChI: InChI=1S/C10H18N2O4S/c1-4-5-6-7(13)11-8(9(14)15)10(2,3)17-12-16/h8H,4-6H2,1-3H3,(H,11,13)(H,14,15)
• InChIKey: QCRZCAKMRYXQNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-methyl-3-(nitrososulfanyl)-2-pentanamidobutanoic acid
• IUPAC Traditional name: 3-methyl-3-(nitrososulfanyl)-2-pentanamidobutanoic acid
• Synonyms: SNVP; 3-(Nitrosothio)-N-(1-oxopentyl)valine; S-Nitroso-N-valeryl-D,L-penicillamine

Database IDs

• CAS Number: 225233-99-8
• PubChem SID: 164231433
• PubChem CID: 5232

CALCULATED PROPERTIES

• Acid pKa: 3.6487653
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.13765559
• LogD (pH = 7.4): -1.3394008
• Log P: 1.9860213
• Molar Refractivity: 65.7567 cm^3
• Polarizability: 25.173197 Å^3
• Polar Surface Area: 95.83 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Green Solid
• Melting Point: 98-101°C

Safety Information

• Storage Condition: -86°C Freezer
• Storage Warning: Temperature Sensitive

DETAILS

Toronto Research Chemicals - N548500

Exhibits higher lipophilicity and greater stability in solution than SNAP (N522500). Its decompostion is accelerated by the presence of Cu(II) and cysteine.

REFERENCES

• Megson, I.L, et al.: Br. J. Pharmacol., 126, 639 (1999)