1-{2-[(2S)-2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one

• ChemBase ID: 176984
• Molecular Formular: C21H27NO3
• Molecular Mass: 341.44398
• Monoisotopic Mass: 341.19909373
• SMILES: c1cccc(c1C(=O)CCc1ccccc1)OC[C@@H](O)CNCCC
• Canonical SMILES: CCCNC[C@@H](COc1ccccc1C(=O)CCc1ccccc1)O
• InChI: InChI=1S/C21H27NO3/c1-2-14-22-15-18(23)16-25-21-11-7-6-10-19(21)20(24)13-12-17-8-4-3-5-9-17/h3-11,18,22-23H,2,12-16H2,1H3/t18-/m0/s1
• InChIKey: JWHAUXFOSRPERK-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{2-[(2S)-2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
• IUPAC Traditional name: 1-{2-[(2S)-2-hydroxy-3-(propylamino)propoxy]phenyl}-3-phenylpropan-1-one
• Synonyms: 1-[2-[(2S)-2-hydroxy-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone; (-)-(S)-Propafenone; (-)-Propafenone; (S)-Propafenone

Database IDs

• CAS Number: 107381-32-8
• PubChem SID: 164232894
• PubChem CID: 184820

CALCULATED PROPERTIES

• Acid pKa: 14.085882
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.34713113
• LogD (pH = 7.4): 1.3413471
• Log P: 3.5367227
• Molar Refractivity: 100.2064 cm^3
• Polarizability: 39.38228 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P757496

Sodium channel blocker. Antiarrhythmic (class IC).

REFERENCES

• Hollmann, M., et al.: Arzneim.-Forsch., 33, 763 (1983)
• Bryson, H. M., et al.:Drugs, 45, 85 (1983)
• Rae, A. P., et al.: Am. J. Cardiol., 82, 59N (1983)