1-(5-amino-2-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethan-1-one

• ChemBase ID: 166026
• Molecular Formular: C14H22N2O3
• Molecular Mass: 266.33608
• Monoisotopic Mass: 266.16304257
• SMILES: c1c(ccc(c1C(=O)C)OCC(CNC(C)C)O)N
• Canonical SMILES: OC(COc1ccc(cc1C(=O)C)N)CNC(C)C
• InChI: InChI=1S/C14H22N2O3/c1-9(2)16-7-12(18)8-19-14-5-4-11(15)6-13(14)10(3)17/h4-6,9,12,16,18H,7-8,15H2,1-3H3
• InChIKey: DBUJVRULIBQHKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(5-amino-2-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)ethan-1-one
• IUPAC Traditional name: 1-{5-amino-2-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}ethanone
• Synonyms: (+/-)-1-[5-Amino-2-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]phenyl]ethanone; DL-1-(2-Acetyl-4-aminophenoxy)-3-isopropylaminopropan-2-ol; M and B 17127; rac N-Desbutyroyl Acebutolol

Database IDs

• CAS Number: 57898-80-3
• PubChem SID: 162260159
• PubChem CID: 155703

CALCULATED PROPERTIES

• Acid pKa: 14.076013
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.8762228
• LogD (pH = 7.4): -1.8117639
• Log P: 0.32294074
• Molar Refractivity: 75.4787 cm^3
• Polarizability: 29.078064 Å^3
• Polar Surface Area: 84.58 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D282000

The major metabolite of Acebutolol (A123800).

REFERENCES

• Elsayed, M., et al.: Anal. Lett., 22, 1665 (1989)
• Bonazzi, D., et al.: J. Pharma. Biomed. Anal., 16, 431 (1989)