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

• ChemBase ID: 159147
• Molecular Formular: C12H15NO3S
• Molecular Mass: 253.3174
• Monoisotopic Mass: 253.07726435
• SMILES: C(SC[C@@H](NC(=O)C)C(=O)O)c1ccccc1
• Canonical SMILES: CC(=O)N[C@@H](C(=O)O)CSCc1ccccc1
• InChI: InChI=1S/C12H15NO3S/c1-9(14)13-11(12(15)16)8-17-7-10-5-3-2-4-6-10/h2-6,11H,7-8H2,1H3,(H,13,14)(H,15,16)/t11-/m1/s1
• InChIKey: BJUXDERNWYKSIQ-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(benzylsulfanyl)-2-acetamidopropanoic acid
• IUPAC Traditional name: (2S)-3-(benzylsulfanyl)-2-acetamidopropanoic acid
• Synonyms: N-Acetyl-S-(phenylmethyl)-L-cysteine; N-Acetyl-3-(benzylthio)-alanine; Benzylmercapturic Acid; Acetyl Benzyl Cysteine; S-Benzylmercapturic Acid; N-Acetyl-S-benzyl-L-cysteine

Database IDs

• CAS Number: 19542-77-9
• PubChem SID: 162253282
• PubChem CID: 853882

CALCULATED PROPERTIES

• Acid pKa: 3.98924
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.22342509
• LogD (pH = 7.4): -1.8688183
• Log P: 1.2963916
• Molar Refractivity: 66.9802 cm^3
• Polarizability: 26.176975 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 144-146°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A168428

A metabolite of Toluene.

REFERENCES

• Gargas, M., et al.: Toxicol. Appl. Pharmacol., 98, 87 (1989)
• Commandeur, J., et al.: Pharmacol. Rev., 47(1989)
• 271 (1989)
• Campo, P., et al.: Neurotoxicol. Teratol., 21, 427 (1989)
• Lohse, C., et al.: J. Agr. Food Chem., 48, 5913 (1989)