3-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}propanoic acid

• ChemBase ID: 168188
• Molecular Formular: C15H23NO4
• Molecular Mass: 281.34742
• Monoisotopic Mass: 281.16270822
• SMILES: c1c(ccc(c1)CCC(=O)O)OC[C@H](CNC(C)C)O
• Canonical SMILES: O[C@H](COc1ccc(cc1)CCC(=O)O)CNC(C)C
• InChI: InChI=1S/C15H23NO4/c1-11(2)16-9-13(17)10-20-14-6-3-12(4-7-14)5-8-15(18)19/h3-4,6-7,11,13,16-17H,5,8-10H2,1-2H3,(H,18,19)/t13-/m0/s1
• InChIKey: ILSCWPMGTDPATI-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenyl}propanoic acid
• IUPAC Traditional name: 3-{4-[(2S)-2-hydroxy-3-(isopropylamino)propoxy]phenyl}propanoic acid
• Synonyms: 4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzenepropanoic Acid; (S)-Esmolol Acid

Database IDs

• PubChem SID: 162262320
• PubChem CID: 71316428

CALCULATED PROPERTIES

• Acid pKa: 3.8448966
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.8026644
• LogD (pH = 7.4): -0.79700065
• Log P: -0.79586524
• Molar Refractivity: 76.2841 cm^3
• Polarizability: 30.24221 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E668025

The S-enantiomer metabolite of Esmolol (E668000) in humans.

REFERENCES

• Jahn, P., et al.: Arzneim.Forsch., 45, 536 (1995)
• Nassar, A., et al.: Curr Drug Metab., 4, 259 (1995)