4-[(2R)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]naphthalen-1-ol hydrobromide

• ChemBase ID: 171202
• Molecular Formular: C16H22BrNO3
• Molecular Mass: 356.25478
• Monoisotopic Mass: 355.07830557
• SMILES: c1cccc2c1c(ccc2O)OC[C@@H](CNC(C)C)O.Br
• Canonical SMILES: O[C@@H](COc1ccc(c2c1cccc2)O)CNC(C)C.Br
• InChI: InChI=1S/C16H21NO3.BrH/c1-11(2)17-9-12(18)10-20-16-8-7-15(19)13-5-3-4-6-14(13)16;/h3-8,11-12,17-19H,9-10H2,1-2H3;1H/t12-;/m1./s1
• InChIKey: LHTJAZGMMZLACD-UTONKHPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(2R)-2-hydroxy-3-[(propan-2-yl)amino]propoxy]naphthalen-1-ol hydrobromide
• IUPAC Traditional name: 4-[(2R)-2-hydroxy-3-(isopropylamino)propoxy]naphthalen-1-ol hydrobromide
• Synonyms: 4-[(2R)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrobromide; (+)-4-Hydroxypropranolol Hydrobromide; (+)-Hydroxypropranolol Hydrobromide; (R)-4-Hydroxy Propranolol Hydrobromide

Database IDs

• PubChem SID: 164227112
• PubChem CID: 71749300

CALCULATED PROPERTIES

• Acid pKa: 9.301043
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.90915066
• LogD (pH = 7.4): 0.084633276
• Log P: 1.5727339
• Molar Refractivity: 78.8066 cm^3
• Polarizability: 32.33075 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 147-149°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H952530

The main metabolite of (R)-Propranolol.

REFERENCES

• Shwed, J., et al.: Xenobiotica, 22, 973 (1992)
• Fujita, K., et al.: Biol. Pharm. Bull., 22, 446 (1992)
• Walle, U., et al.: Drug Metab. Dispos., 30, 564 (1992)