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

• ChemBase ID: 172565
• Molecular Formular: C16H25NO3
• Molecular Mass: 279.3746
• Monoisotopic Mass: 279.18344367
• SMILES: c1cc(ccc1CC(N(CCCC(=O)O)CC)C)OC
• Canonical SMILES: CCN(C(Cc1ccc(cc1)OC)C)CCCC(=O)O
• InChI: InChI=1S/C16H25NO3/c1-4-17(11-5-6-16(18)19)13(2)12-14-7-9-15(20-3)10-8-14/h7-10,13H,4-6,11-12H2,1-3H3,(H,18,19)
• InChIKey: UZUWRVLVHOYTNN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 475203-77-1
• PubChem SID: 164228475
• PubChem CID: 20556914

CALCULATED PROPERTIES

• Acid pKa: 4.4463205
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.061772756
• LogD (pH = 7.4): 0.09132561
• Log P: 0.09094376
• Molar Refractivity: 80.5253 cm^3
• Polarizability: 31.376356 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 83-87°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M202500

A metabolite of Mebeverine (M202490), an antispasmodic. Mebeverine acid appears to be a valuable marker of oral exposure to Mebeverine.

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)