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

• ChemBase ID: 174589
• Molecular Formular: C14H21NO4
• Molecular Mass: 267.32084
• Monoisotopic Mass: 267.14705816
• SMILES: CC(NCC(COc1ccc(cc1)CC(=O)O)O)C
• Canonical SMILES: OC(COc1ccc(cc1)CC(=O)O)CNC(C)C
• InChI: InChI=1S/C14H21NO4/c1-10(2)15-8-12(16)9-19-13-5-3-11(4-6-13)7-14(17)18/h3-6,10,12,15-16H,7-9H2,1-2H3,(H,17,18)
• InChIKey: PUQIRTNPJRFRCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)acetic acid
• IUPAC Traditional name: {4-[2-hydroxy-3-(isopropylamino)propoxy]phenyl}acetic acid
• Synonyms: 4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetic Acid; 4-(2-Hydroxy-3-isopropylaminopropoxy)phenylacetic Acid; Atenolol Acid; H 117/04; SL 77-010; Metoprolol Acid

Database IDs

• CAS Number: 56392-14-4
• PubChem SID: 164230499
• PubChem CID: 62936

CALCULATED PROPERTIES

• Acid pKa: 3.54494
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.2434254
• LogD (pH = 7.4): -1.2416159
• Log P: -1.2404048
• Molar Refractivity: 71.6831 cm^3
• Polarizability: 28.40387 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-white Solid
• Melting Point: 174-176°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M338785

The acidic inactive metabolite of Metoprolol.

REFERENCES

• Erhardt, et al.: J. Med. Chem., 25, 1408 (1982)
• Bodor, N., et al.: Pharmaceutical Res., 3, 120 (1982)