(2S)-3-(acetylsulfanyl)-2-acetamidopropanoic acid

• ChemBase ID: 166756
• Molecular Formular: C7H11NO4S
• Molecular Mass: 205.23154
• Monoisotopic Mass: 205.04087884
• SMILES: C([C@@H](NC(=O)C)C(=O)O)SC(=O)C
• Canonical SMILES: CC(=O)SC[C@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C7H11NO4S/c1-4(9)8-6(7(11)12)3-13-5(2)10/h6H,3H2,1-2H3,(H,8,9)(H,11,12)/t6-/m1/s1
• InChIKey: HSPYGHDTVQJUDE-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(acetylsulfanyl)-2-acetamidopropanoic acid
• IUPAC Traditional name: (2S)-3-(acetylsulfanyl)-2-acetamidopropanoic acid
• Synonyms: N-Acetylcysteine Acetate; Dacisteine; N,S-Diacetylcysteine; N-Acetylcysteine S-Acetate; N,S-Diacetyl-L-cysteine

Database IDs

• CAS Number: 18725-37-6
• PubChem SID: 162260889
• PubChem CID: 12850517

CALCULATED PROPERTIES

• Acid pKa: 3.533996
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.8296778
• LogD (pH = 7.4): -4.2356577
• Log P: -0.8707052
• Molar Refractivity: 47.1352 cm^3
• Polarizability: 18.67838 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 114-116°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D312300

A double-prodrugs of L-cysteine: differential protection against acetaminophen-induced hepatotoxicity in mice.

REFERENCES

• Vina, J., et al.: Biochem. J., 170, 627 (1978)
• Roberts, J., et al.: J. Med. Chem., 30, 1891 (1978)
• Nagasawa, H., et al.: J. Biochem. Toxicol., 11, 289 (1978)