4-[2-hydroxy-3-(propylamino)propoxy]naphthalen-1-ol

• ChemBase ID: 171209
• Molecular Formular: C16H21NO3
• Molecular Mass: 275.34284
• Monoisotopic Mass: 275.15214354
• SMILES: c1(ccc(c2c1cccc2)O)OCC(CNCCC)O
• Canonical SMILES: CCCNCC(COc1ccc(c2c1cccc2)O)O
• InChI: InChI=1S/C16H21NO3/c1-2-9-17-10-12(18)11-20-16-8-7-15(19)13-5-3-4-6-14(13)16/h3-8,12,17-19H,2,9-11H2,1H3
• InChIKey: VNEVYWUJEGCYPZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-hydroxy-3-(propylamino)propoxy]naphthalen-1-ol
• IUPAC Traditional name: 4-[2-hydroxy-3-(propylamino)propoxy]naphthalen-1-ol
• Synonyms: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]-1-naphthalenol Hydrochloride; rac-4-Hydroxy Propranolol Hydrochloride

Database IDs

• CAS Number: 14133-90-5
• PubChem SID: 164227119
• PubChem CID: 45039504

CALCULATED PROPERTIES

• Acid pKa: 9.328618
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.80977964
• LogD (pH = 7.4): 0.13554987
• Log P: 1.6619642
• Molar Refractivity: 78.9118 cm^3
• Polarizability: 32.33075 Å^3
• Polar Surface Area: 61.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Pale Purple Solid
• Melting Point: 167-169°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H952545

A metabolite of Propranolol.

REFERENCES

• Walle, T., et al.: Drug Metab. Dispos., 13, 204 (1985)
• Mason, R., et al.: J. Med. Chem., 34, 869 (1985)
• Anderson, R., et al.: Biochem. Pharmacol., 52, 341 (1985)
• Hung, D., et al.: J. Pharmacol. Exp. Ther., 297, 780 (1985)