tert-butyl (2S)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoate

• ChemBase ID: 159314
• Molecular Formular: C12H22N2O5S
• Molecular Mass: 306.37848
• Monoisotopic Mass: 306.12494281
• SMILES: C([C@H](C(=O)OC(C)(C)C)NC(=O)C)SCC(C(=O)N)O
• Canonical SMILES: OC(C(=O)N)CSC[C@H](C(=O)OC(C)(C)C)NC(=O)C
• InChI: InChI=1S/C12H22N2O5S/c1-7(15)14-8(11(18)19-12(2,3)4)5-20-6-9(16)10(13)17/h8-9,16H,5-6H2,1-4H3,(H2,13,17)(H,14,15)/t8-,9?/m1/s1
• InChIKey: WAGGQWFETBDNLY-VEDVMXKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl (2S)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoate
• IUPAC Traditional name: tert-butyl (2S)-3-[(2-carbamoyl-2-hydroxyethyl)sulfanyl]-2-acetamidopropanoate
• Synonyms: N-Acetyl-S-(3-amino-2-hydroxy-3-oxopropyl)-L-cysteine-1,1-dimethylethyl Ester

Database IDs

• CAS Number: 1079950-08-5
• PubChem SID: 162253449
• PubChem CID: 71312917

CALCULATED PROPERTIES

• Acid pKa: 12.213428
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.1912404
• LogD (pH = 7.4): -1.1912464
• Log P: -1.1912403
• Molar Refractivity: 75.0407 cm^3
• Polarizability: 29.825235 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-white Solid

DETAILS

Toronto Research Chemicals - A178990

Protected metabolite of Acrylamide.

REFERENCES

• Bjellaas, T., et al.: Toxicol. Sci., 100, 374 (2007)
• Doerge, D., et al.: Toxicol. Lett., 169, 34 (2007)
• Hartmann, E., et al.: J. Agric. Food Chem., 56, 6061 (2007)