N-(3-butanoyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide hydrochloride

• ChemBase ID: 165439
• Molecular Formular: C20H33ClN2O4
• Molecular Mass: 400.94002
• Monoisotopic Mass: 400.21288523
• SMILES: c1c(ccc(c1C(=O)CCC)OCC(CNC(C)C)O)NC(=O)CCC.Cl
• Canonical SMILES: CCCC(=O)c1cc(ccc1OCC(CNC(C)C)O)NC(=O)CCC.Cl
• InChI: InChI=1S/C20H32N2O4.ClH/c1-5-7-18(24)17-11-15(22-20(25)8-6-2)9-10-19(17)26-13-16(23)12-21-14(3)4;/h9-11,14,16,21,23H,5-8,12-13H2,1-4H3,(H,22,25);1H
• InChIKey: NOQLJJJTTFSZOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-butanoyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)butanamide hydrochloride
• IUPAC Traditional name: N-{3-butanoyl-4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}butanamide hydrochloride
• Synonyms: (+/-)-N-[4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-3-(1-oxobutyl)phenyl]butanamide Hydrochloride; N-[3-Butanoyl-4-[(2RS)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]butanamide Hydrochloride; rac 3-Deacetyl-3-butanoyl Acebutolol Hydrochloride

Database IDs

• CAS Number: 57898-71-2
• PubChem SID: 162259572
• PubChem CID: 71315201

CALCULATED PROPERTIES

• Acid pKa: 13.921873
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.50165904
• LogD (pH = 7.4): 0.5453093
• Log P: 2.679786
• Molar Refractivity: 104.0971 cm^3
• Polarizability: 40.182816 Å^3
• Polar Surface Area: 87.66 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D198500

Acebutolol (A123800) impurity; a cardioselective β-adrenergic blocker agent.

REFERENCES

• Basil, B., et al.: J. Med. Chem., 19, 399 (1976)