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

• ChemBase ID: 175421
• Molecular Formular: C7H12N2O4S
• Molecular Mass: 220.24618
• Monoisotopic Mass: 220.05177787
• SMILES: S(C([C@H](NC(=O)C)C(=O)O)(C)C)N=O
• Canonical SMILES: O=NSC([C@@H](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)/t5-/m1/s1
• InChIKey: ZIIQCSMRQKCOCT-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 79032-48-7
• PubChem SID: 164231331
• PubChem CID: 157991

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

• Apperance: Green Crystalline Solid

DETAILS

Toronto Research Chemicals - N522050

The D-isomer of SNAP. Serves as an NO donor.

REFERENCES

• Al-Sa’doni, H.H., et al.: Nitriic Oxide, 4,6, 550 (2000)