(2S)-2-acetamido-3-(prop-2-en-1-ylsulfanyl)propanoic acid

• ChemBase ID: 159080
• Molecular Formular: C8H13NO3S
• Molecular Mass: 203.25872
• Monoisotopic Mass: 203.06161428
• SMILES: C(=C)CSC[C@@H](NC(=O)C)C(=O)O
• Canonical SMILES: CC(=O)N[C@@H](C(=O)O)CSCC=C
• InChI: InChI=1S/C8H13NO3S/c1-3-4-13-5-7(8(11)12)9-6(2)10/h3,7H,1,4-5H2,2H3,(H,9,10)(H,11,12)/t7-/m1/s1
• InChIKey: LKRAEHUDIUJBSF-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-acetamido-3-(prop-2-en-1-ylsulfanyl)propanoic acid
• IUPAC Traditional name: (2S)-2-acetamido-3-(prop-2-en-1-ylsulfanyl)propanoic acid
• Synonyms: N-Acetyl-S-2-propen-1-yl-L-cysteine; L-N-Acetyl-3-(allylthio)alanine; Allylmercapturic Acid; S-Allylmercapturic Acid; N-Acetyl-S-allyl-L-cysteine

Database IDs

• CAS Number: 23127-41-5
• PubChem SID: 162253215
• PubChem CID: 10465488

CALCULATED PROPERTIES

• Acid pKa: 4.0191174
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.1879694
• LogD (pH = 7.4): -2.8448346
• Log P: 0.30316833
• Molar Refractivity: 51.5303 cm^3
• Polarizability: 20.06428 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A168100

A component of garlic which revealed antiplatelet, antithrombotic activity and reduced LDL oxidation thus indicating their possible use for cardiovascular disease.

REFERENCES

• Steinberg, D., et al.: J. Biol. Chem., 272, 20963 (1997)
• Lawson, L., et al.: J. Agric. Food Chem., 53, 6254 (1997)
• Gonen, A., et al.: Pathobiology, 72, 325 (1997)