4-[2-(dipropylcarbamoyl)-2-(phenylformamido)ethyl]phenyl benzoate

• ChemBase ID: 166943
• Molecular Formular: C29H32N2O4
• Molecular Mass: 472.57538
• Monoisotopic Mass: 472.23620751
• SMILES: C(=O)(c1ccccc1)Oc1ccc(cc1)CC(C(=O)N(CCC)CCC)NC(=O)c1ccccc1
• Canonical SMILES: CCCN(C(=O)C(NC(=O)c1ccccc1)Cc1ccc(cc1)OC(=O)c1ccccc1)CCC
• InChI: InChI=1S/C29H32N2O4/c1-3-19-31(20-4-2)28(33)26(30-27(32)23-11-7-5-8-12-23)21-22-15-17-25(18-16-22)35-29(34)24-13-9-6-10-14-24/h5-18,26H,3-4,19-21H2,1-2H3,(H,30,32)
• InChIKey: DYDQAHTZBCHHPC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-(dipropylcarbamoyl)-2-(phenylformamido)ethyl]phenyl benzoate
• IUPAC Traditional name: 4-[2-(dipropylcarbamoyl)-2-(phenylformamido)ethyl]phenyl benzoate
• Synonyms: α-(Benzoylamino)-4-(benzoyloxy)-N,N-dipropylbenzenepropanamide; (±)-α-(Benzoylamino)-4-(benzoyloxy)-N,N-dipropylbenzenepropanamide; Tiropramide Impurity B; N,O-Dibenzoyl-DL-tyrosyl-N',N'-dipropylamide

Database IDs

• CAS Number: 57227-08-4
• PubChem SID: 162261076
• PubChem CID: 45489826

CALCULATED PROPERTIES

• Acid pKa: 15.036326
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.8111415
• LogD (pH = 7.4): 5.8111415
• Log P: 5.8111415
• Molar Refractivity: 137.1943 cm^3
• Polarizability: 52.68636 Å^3
• Polar Surface Area: 75.71 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D422680

N,O-Dibenzoyl-DL-tyrosyl-N',N'-dipropylamide is a metabolite of the antispasmodic agent Tiropramide (T446900). Tiropramide impurity B.

REFERENCES

• Janssen, et al.: J. Pharm. Pharmacol., 9, 381 (1956)
• Bertaccini, et al.: Br. J. Pharmac., 34, 310 (1956)