4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenol

• ChemBase ID: 176914
• Molecular Formular: C12H19NO3
• Molecular Mass: 225.28416
• Monoisotopic Mass: 225.13649347
• SMILES: c1c(ccc(c1)OC[C@H](CNC(C)C)O)O
• Canonical SMILES: O[C@H](COc1ccc(cc1)O)CNC(C)C
• InChI: InChI=1S/C12H19NO3/c1-9(2)13-7-11(15)8-16-12-5-3-10(14)4-6-12/h3-6,9,11,13-15H,7-8H2,1-2H3/t11-/m0/s1
• InChIKey: ADUKCCWBEDSMEB-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2S)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]phenol
• IUPAC Traditional name: prenalterol
• Synonyms: 4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]phenol; (-)-Prenalterol; (S)-Prenalterol; Hyprenan; S-Varbian; Prenalterol

Database IDs

• CAS Number: 57526-81-5
• PubChem SID: 164232824
• PubChem CID: 42396

CALCULATED PROPERTIES

• Acid pKa: 10.113282
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.9010023
• LogD (pH = 7.4): -0.92252856
• Log P: 0.7999005
• Molar Refractivity: 62.3564 cm^3
• Polarizability: 24.802814 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P712700

Prenalterol is a β1-adrenergic agonist. Prenalterol is used as an cardiotonic.

REFERENCES

• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2008)
• Scheiber, J., et al.: J. Med. Chem., 52, 3103 (2008)
• Broadley, K., et al.: Biochem. Pharmacol., 80, 1537 (2008)