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

• ChemBase ID: 170599
• Molecular Formular: C13H19NO4
• Molecular Mass: 253.29426
• Monoisotopic Mass: 253.13140809
• SMILES: c1cc(ccc1C(=O)O)OCC(CNC(C)C)O
• Canonical SMILES: OC(COc1ccc(cc1)C(=O)O)CNC(C)C
• InChI: InChI=1S/C13H19NO4/c1-9(2)14-7-11(15)8-18-12-5-3-10(4-6-12)13(16)17/h3-6,9,11,14-15H,7-8H2,1-2H3,(H,16,17)
• InChIKey: WONQRVASZHJNFS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}benzoic acid
• IUPAC Traditional name: 4-[2-hydroxy-3-(isopropylamino)propoxy]benzoic acid
• Synonyms: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzoic Acid; H 112/02; 4-(2-Hydroxy-3-isopropylaminopropoxy)benzoic Acid

Database IDs

• CAS Number: 72570-70-8
• PubChem SID: 164226509
• PubChem CID: 12540204

CALCULATED PROPERTIES

• Acid pKa: 4.358779
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.2440922
• LogD (pH = 7.4): -1.2215236
• Log P: -1.2207314
• Molar Refractivity: 67.6317 cm^3
• Polarizability: 26.542475 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water (sparingly)
• Apperance: White Solid
• Melting Point: 253-255°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H943575

The major metabolite of Bisoprolol (B510500).

REFERENCES

• Heberer, T., et al.: Toxicol. Lett., 131, 5 (2002)
• Boxall, A., et al.: Environ. Sci. Technol., 38, 368A (2002)
• Huschek, G., et al.: Environ. Toxicol., 19, 226 (2002)
• Larsen, T., et al.: J. Biotechnol., 113, 295 (2004)