4-{5-chloro-2-[2-methyl-4-(2-methylbenzamido)benzamido]phenyl}-4-oxobutanoic acid

• ChemBase ID: 178730
• Molecular Formular: C26H23ClN2O5
• Molecular Mass: 478.92422
• Monoisotopic Mass: 478.12954953
• SMILES: c1(ccccc1C)C(=O)Nc1ccc(c(c1)C)C(=O)Nc1c(cc(cc1)Cl)C(=O)CCC(=O)O
• Canonical SMILES: OC(=O)CCC(=O)c1cc(Cl)ccc1NC(=O)c1ccc(cc1C)NC(=O)c1ccccc1C
• InChI: InChI=1S/C26H23ClN2O5/c1-15-5-3-4-6-19(15)25(33)28-18-8-9-20(16(2)13-18)26(34)29-22-10-7-17(27)14-21(22)23(30)11-12-24(31)32/h3-10,13-14H,11-12H2,1-2H3,(H,28,33)(H,29,34)(H,31,32)
• InChIKey: PRTSBHBGYFDAAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{5-chloro-2-[2-methyl-4-(2-methylbenzamido)benzamido]phenyl}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{5-chloro-2-[2-methyl-4-(2-methylbenzamido)benzamido]phenyl}-4-oxobutanoic acid
• Synonyms: 2-[[4-[(2-methylbenzoyl)amino]-2-methylbenzoyl]amino]-γ-oxo-5-chlorobenzenebutanoic Acid; Tolvaptan Impurity 1; Tolvaptan γ-Oxobutanoic Acid Impurity

Database IDs

• PubChem SID: 164234640
• PubChem CID: 71752623

CALCULATED PROPERTIES

• Acid pKa: 3.4936433
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.8226228
• LogD (pH = 7.4): 2.4427352
• Log P: 5.820413
• Molar Refractivity: 133.3083 cm^3
• Polarizability: 48.90137 Å^3
• Polar Surface Area: 112.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T536665

A Tolvaptan (T536650) Impurity.

REFERENCES

• Paterna, S., et al.: Eur. J. Heart Fail, 2, 305 (2000)
• Udelson, J., et al.: Circulation, 104, 2417 (2000)
• Goldsmith, S., et al.: J. Am. Coll Cardiol., 46, 1785 (2000)