({1-[4-hydroxy-2-(3-phenylpropanoyl)phenoxy]-3-(propylamino)propan-2-yl}oxy)sulfonic acid

• ChemBase ID: 171193
• Molecular Formular: C21H27NO7S
• Molecular Mass: 437.50658
• Monoisotopic Mass: 437.15082321
• SMILES: c1c(ccc(c1C(=O)CCc1ccccc1)OCC(CNCCC)OS(=O)(=O)O)O
• Canonical SMILES: CCCNCC(OS(=O)(=O)O)COc1ccc(cc1C(=O)CCc1ccccc1)O
• InChI: InChI=1S/C21H27NO7S/c1-2-12-22-14-18(29-30(25,26)27)15-28-21-11-9-17(23)13-19(21)20(24)10-8-16-6-4-3-5-7-16/h3-7,9,11,13,18,22-23H,2,8,10,12,14-15H2,1H3,(H,25,26,27)
• InChIKey: UUVDTMZGLJHIMA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({1-[4-hydroxy-2-(3-phenylpropanoyl)phenoxy]-3-(propylamino)propan-2-yl}oxy)sulfonic acid
• IUPAC Traditional name: {1-[4-hydroxy-2-(3-phenylpropanoyl)phenoxy]-3-(propylamino)propan-2-yl}oxysulfonic acid
• Synonyms: 1-[5-Hydroxy-2-[2-sulfo-3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone; 1-[5-Hydroxy-2-[3-(propylamino)propoxy]phenyl]-3-phenyl-1-propanone Sulfate; 5-Hydroxy Propafenone Sulfate

Database IDs

• PubChem SID: 164227103
• PubChem CID: 71749294

CALCULATED PROPERTIES

• Acid pKa: -1.8878433
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 2.0694234
• LogD (pH = 7.4): 2.046455
• Log P: 2.0697162
• Molar Refractivity: 112.1791 cm^3
• Polarizability: 44.714447 Å^3
• Polar Surface Area: 122.16 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952465

A metabolite of Propafenone (P757495), a sodium channel blocker.

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)