4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoic acid

• ChemBase ID: 166513
• Molecular Formular: C15H23NO3
• Molecular Mass: 265.34802
• Monoisotopic Mass: 265.1677936
• SMILES: c1c(ccc(c1)CC(N(CCCC(=O)O)CC)C)O
• Canonical SMILES: CCN(C(Cc1ccc(cc1)O)C)CCCC(=O)O
• InChI: InChI=1S/C15H23NO3/c1-3-16(10-4-5-15(18)19)12(2)11-13-6-8-14(17)9-7-13/h6-9,12,17H,3-5,10-11H2,1-2H3,(H,18,19)
• InChIKey: DJTCBAFIXOMULT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoic acid
• IUPAC Traditional name: 4-{ethyl[1-(4-hydroxyphenyl)propan-2-yl]amino}butanoic acid
• Synonyms: 4-[Ethyl[2-(4-hydroxyphenyl)-1-methylethyl]amino]butanoic Acid; O-Desmethyl Mebeverine Acid

Database IDs

• CAS Number: 586357-02-0
• PubChem SID: 162260646
• PubChem CID: 45038887

CALCULATED PROPERTIES

• Acid pKa: 4.4540415
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.08462845
• LogD (pH = 7.4): -0.055471618
• Log P: -0.05531213
• Molar Refractivity: 76.043 cm^3
• Polarizability: 29.463535 Å^3
• Polar Surface Area: 60.77 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D292055

A metabolite of Mebeverine (M202490), an antispasmodic.

REFERENCES

• Greenwood, B., et al.: Eur. J. Pharmacol., 211, 143 (1992)
• van Outryve, M., et al.: J. Clin. Pharm. Ther., 20, 277 (1992)
• Kraemer, T., et al.: Drug Metab. Disp., 28, 339 (1992)