(2R)-2-acetamido-3-(methylsulfanyl)propanoic acid

• ChemBase ID: 159362
• Molecular Formular: C6H11NO3S
• Molecular Mass: 177.22144
• Monoisotopic Mass: 177.04596422
• SMILES: C([C@H](NC(=O)C)C(=O)O)SC
• Canonical SMILES: CSC[C@@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C6H11NO3S/c1-4(8)7-5(3-11-2)6(9)10/h5H,3H2,1-2H3,(H,7,8)(H,9,10)/t5-/m0/s1
• InChIKey: RYGLCORNOFFGTB-YFKPBYRVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-acetamido-3-(methylsulfanyl)propanoic acid
• IUPAC Traditional name: (2R)-2-acetamido-3-(methylsulfanyl)propanoic acid
• Synonyms: S-Methylmercapturic Acid; N-Acetyl-S-methyl-L-cysteine

Database IDs

• CAS Number: 16637-59-5
• PubChem SID: 162253497
• PubChem CID: 13893975

CALCULATED PROPERTIES

• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 3.9135094
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.9169819
• LogD (pH = 7.4): -3.5308635
• Log P: -0.32430354
• Molar Refractivity: 42.3184 cm^3
• Polarizability: 16.665525 Å^3
• Polar Surface Area: 66.4 Å^2

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 83-85°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A186640

A metabolite of acetaminophen (A161220).

REFERENCES

• Lohse, C., et al.: J. Agric. Food Chem., 48, 5913 (2000)
• Perrey, D., et al.: Bioorg. Med. Chem. Lett., 10, 551 (2000)