(2S)-1-[(2S)-2-{[(2S)-1-butoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 167921
• Molecular Formular: C22H32N2O5
• Molecular Mass: 404.49988
• Monoisotopic Mass: 404.23112213
• SMILES: C1C[C@H](N(C1)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCCCC)C)C(=O)O
• Canonical SMILES: CCCCOC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C22H32N2O5/c1-3-4-15-29-22(28)18(13-12-17-9-6-5-7-10-17)23-16(2)20(25)24-14-8-11-19(24)21(26)27/h5-7,9-10,16,18-19,23H,3-4,8,11-15H2,1-2H3,(H,26,27)/t16-,18-,19-/m0/s1
• InChIKey: ANOQNYRWFAERCM-WDSOQIARSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(2S)-1-butoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-{[(2S)-1-butoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: (S)-1-[N-[3-Phenyl-1-[(butoxycarbonyl]propyl]-L-alanyl]-L-proline Hydrochloride Salt; Enalaprilat Butyl Ester Hydrochloride Salt

Database IDs

• PubChem SID: 162262054
• PubChem CID: 10179377

CALCULATED PROPERTIES

• Acid pKa: 3.6713302
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2663733
• LogD (pH = 7.4): -0.08818145
• Log P: 1.5548738
• Molar Refractivity: 108.6996 cm^3
• Polarizability: 43.095577 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555385

Enalaprilat butyl ester is an impurity of Enalaprilat maleate.

REFERENCES

• Theohanson, et al.: J. Biol. Chem., 175, 833 (1948)