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

• ChemBase ID: 159214
• Molecular Formular: C8H12N2O3S
• Molecular Mass: 216.25748
• Monoisotopic Mass: 216.05686325
• SMILES: C(SC[C@@H](NC(=O)C)C(=O)O)CC#N
• Canonical SMILES: CC(=O)N[C@@H](C(=O)O)CSCCC#N
• InChI: InChI=1S/C8H12N2O3S/c1-6(11)10-7(8(12)13)5-14-4-2-3-9/h7H,2,4-5H2,1H3,(H,10,11)(H,12,13)/t7-/m1/s1
• InChIKey: VDKVYEUEJCNDHM-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-[(2-cyanoethyl)sulfanyl]-2-acetamidopropanoic acid
• IUPAC Traditional name: (2S)-3-[(2-cyanoethyl)sulfanyl]-2-acetamidopropanoic acid
• Synonyms: N-Acetyl-S-(2-cyanoethyl)cysteine; S-(2-Cyanoethyl)mercapturic Acid; N-Acetyl-S-(2-cyanoethyl)-L-cysteine

Database IDs

• CAS Number: 74514-75-3
• PubChem SID: 162253349
• PubChem CID: 29970737

CALCULATED PROPERTIES

• Acid pKa: 2.5762691
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.4832425
• LogD (pH = 7.4): -4.1631
• Log P: -0.6551366
• Molar Refractivity: 52.1309 cm^3
• Polarizability: 20.215033 Å^3
• Polar Surface Area: 90.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol; Water
• Apperance: White Solid
• Melting Point: 115-118°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A172088

A metabolite of Acrylonitrile (AN) and acrylamide (AM). Are commonly used in the synthesis of plastics and polymers.

REFERENCES

• van Bladeren, P., et al.: Drug Metab. Dispos., 9, 246 (1981)
• Guengerich, F., et al.: Chem. Res. Toxicol., 4, 168 (1981)