N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide

• ChemBase ID: 166740
• Molecular Formular: C16H24N2O4
• Molecular Mass: 308.37276
• Monoisotopic Mass: 308.17360726
• SMILES: c1(ccc(cc1C(=O)C)NC(=O)C)OCC(CNC(C)C)O
• Canonical SMILES: OC(COc1ccc(cc1C(=O)C)NC(=O)C)CNC(C)C
• InChI: InChI=1S/C16H24N2O4/c1-10(2)17-8-14(21)9-22-16-6-5-13(18-12(4)20)7-15(16)11(3)19/h5-7,10,14,17,21H,8-9H2,1-4H3,(H,18,20)
• InChIKey: AWOGXJOBNAWQSF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-acetyl-4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetamide
• IUPAC Traditional name: diacetolol
• Synonyms: (±)-N-[3-Acetyl-4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]acetamide; DL-3'-Acetyl-4'-[2-hydroxy-3-(isopropylamino)propoxy]acetanilide; (±)-Diacetolol; Diacetolol; 1-(4-Acetamido-2-acetylphenoxy)-2-hydroxy-3-isopropylaminopropane; DL-1-(2-Acetyl-4-acetamidophenoxy)-2-hydroxy-3-isopropylaminopropane; Acetylacebutolol; M and B 16942; rac Diacetolol

Database IDs

• CAS Number: 22568-64-5
• PubChem SID: 162260873
• PubChem CID: 50894

CALCULATED PROPERTIES

• Acid pKa: 13.960004
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.791868
• LogD (pH = 7.4): -1.7448997
• Log P: 0.38957706
• Molar Refractivity: 85.6413 cm^3
• Polarizability: 32.829224 Å^3
• Polar Surface Area: 87.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D305200

The principal metabolite of Acebutolol (A123800) with less β-adrenoceptor blocking potency but greater cardioselectivity (atrial relative to tracheal tissue).

REFERENCES

• Basil, B. et al.: Nouv. Pres, Med., 7, 3258 (1978)
• Choi, S. et al.: Arch. Pharm. Res., 25, 541 (1978)
• Basil, B. et al.: Eur. J. Pharmacol., 80, 47 (1978)