(2S)-N-benzyl-2-acetamido-3-(2H3)methoxypropanamide

• ChemBase ID: 172156
• Molecular Formular: C13H18N2O3
• Molecular Mass: 250.29362
• Monoisotopic Mass: 250.13174245
• SMILES: c1(CNC(=O)[C@H](COC)NC(=O)C)ccccc1
• Canonical SMILES: COC[C@@H](C(=O)NCc1ccccc1)NC(=O)C
• InChI: InChI=1S/C13H18N2O3/c1-10(16)15-12(9-18-2)13(17)14-8-11-6-4-3-5-7-11/h3-7,12H,8-9H2,1-2H3,(H,14,17)(H,15,16)/t12-/m0/s1
• InChIKey: VPPJLAIAVCUEMN-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-benzyl-2-acetamido-3-(^2H₃)methoxypropanamide
• IUPAC Traditional name: (2S)-N-benzyl-2-acetamido-3-(^2H₃)methoxypropanamide
• Synonyms: (2R)-2-(Acetylamino)-3-(methoxy-d3)-N-(phenylmethyl)propanamide; (2R)-2-(Acetamido-d3)-N-benzyl-3-methoxypropanamide; ADD 243037-d3; Erlosamide-d3; Harkoseride-d3; Lacosamide-d3; SPM 927-d3; Vimpat-d3; Lacosamide-d3

Database IDs

• PubChem SID: 164228066
• PubChem CID: 71749711

CALCULATED PROPERTIES

• Acid pKa: 12.468967
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.022441689
• LogD (pH = 7.4): -0.022444889
• Log P: -0.022441605
• Molar Refractivity: 67.5675 cm^3
• Polarizability: 26.340395 Å^3
• Polar Surface Area: 67.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chlorform; Methanol
• Apperance: Off-White to Pale Pink
• Melting Point: 143-145°C

Safety Information

• Storage Condition: Refrigerator

REFERENCES

• Lees, G., et al.: Brain Res., 612, 190 (1993)
• Kuo, C., et al.: Mol. Pharmacol., 51, 1077 (1993)
• Barton, M., et al.: Epilepsy Res., 47, 217 (1993)
• Beyreuther, B., et al.: Eur. J. Pharmacol., 539, 64 (1993)
• Beyreuther, B., et al.: CNS Drug Rev., 13, 21