3-(4-hydroxyphenyl)-2-(phenylformamido)-N,N-dipropylpropanamide

• ChemBase ID: 161315
• Molecular Formular: C22H28N2O3
• Molecular Mass: 368.46932
• Monoisotopic Mass: 368.20999277
• SMILES: c1c(ccc(c1)CC(C(=O)N(CCC)CCC)NC(=O)c1ccccc1)O
• Canonical SMILES: CCCN(C(=O)C(NC(=O)c1ccccc1)Cc1ccc(cc1)O)CCC
• InChI: InChI=1S/C22H28N2O3/c1-3-14-24(15-4-2)22(27)20(16-17-10-12-19(25)13-11-17)23-21(26)18-8-6-5-7-9-18/h5-13,20,25H,3-4,14-16H2,1-2H3,(H,23,26)
• InChIKey: VIXHHPJUMYBSCY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(4-hydroxyphenyl)-2-(phenylformamido)-N,N-dipropylpropanamide
• IUPAC Traditional name: 3-(4-hydroxyphenyl)-2-(phenylformamido)-N,N-dipropylpropanamide
• Synonyms: (±)-α-(Benzoylamino)-4-hydroxy-N,N-dipropylbenzenepropanamide; CR 1936; N-Benzoyl-DL-tyrosil-N’,N’-dipropylamide; Tiropramide Impurity C; N-Benzoyl-DL-tyrosyl-N',N'-dipropylamide

Database IDs

• CAS Number: 57227-09-5
• PubChem SID: 162255450
• PubChem CID: 45358872

CALCULATED PROPERTIES

• Acid pKa: 9.503956
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8460982
• LogD (pH = 7.4): 3.8427558
• Log P: 3.846141
• Molar Refractivity: 107.3723 cm^3
• Polarizability: 41.138664 Å^3
• Polar Surface Area: 69.64 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B209860

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

REFERENCES

• Setnikar, I. et al.: Arzneim.-Forsch., 39, 328 (1989)