(2S)-3-[(2-carbamoylethyl)sulfanyl]-2-acetamidopropanoic acid

• ChemBase ID: 159188
• Molecular Formular: C8H14N2O4S
• Molecular Mass: 234.27276
• Monoisotopic Mass: 234.06742794
• SMILES: C(=O)(CCSC[C@@H](NC(=O)C)C(=O)O)N
• Canonical SMILES: NC(=O)CCSC[C@H](C(=O)O)NC(=O)C
• InChI: InChI=1S/C8H14N2O4S/c1-5(11)10-6(8(13)14)4-15-3-2-7(9)12/h6H,2-4H2,1H3,(H2,9,12)(H,10,11)(H,13,14)/t6-/m1/s1
• InChIKey: GGBCHNJZQQEQRX-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-[(2-carbamoylethyl)sulfanyl]-2-acetamidopropanoic acid
• IUPAC Traditional name: (2S)-3-[(2-carbamoylethyl)sulfanyl]-2-acetamidopropanoic acid
• Synonyms: N-Acetyl-S-(3-amino-3-oxopropyl)-L-cysteine; AAMA; N-Acetyl-S-(carbamoylethyl)-L-cysteine

Database IDs

• CAS Number: 81690-92-8
• PubChem SID: 162253323
• PubChem CID: 71312850

CALCULATED PROPERTIES

• Acid pKa: 3.7885163
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.2333212
• LogD (pH = 7.4): -4.787649
• Log P: -1.5200281
• Molar Refractivity: 54.9738 cm^3
• Polarizability: 21.623293 Å^3
• Polar Surface Area: 109.49 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A171870

N-Acetyl-S-(carbamoylethyl)-L-cysteine is the urinary metabolite of Acrylamide (AA). Acrylamide is formed during the heating of food and is classified as a genotoxic carcinogen.

REFERENCES

• Besaratinia, A., et al.: Mutat. Res., 80, 31 (2005)
• Bjellaas, T., et al.: Xenobiotica, 35, 1003 (2005)
• Bjellaas, T., et al.: Food Chem. Toxicol., 45, 1020 (2005)
• Bjellaas, T., et al.: Toxicol. Sci., 98, 110 (2005)