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

• ChemBase ID: 168004
• Molecular Formular: C25H30N2O5
• Molecular Mass: 438.5161
• Monoisotopic Mass: 438.21547207
• SMILES: C1C[C@H](N(C1)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCc1ccccc1)C)C(=O)O
• Canonical SMILES: O=C([C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C25H30N2O5/c1-18(23(28)27-16-8-13-22(27)24(29)30)26-21(15-14-19-9-4-2-5-10-19)25(31)32-17-20-11-6-3-7-12-20/h2-7,9-12,18,21-22,26H,8,13-17H2,1H3,(H,29,30)/t18-,21-,22-/m0/s1
• InChIKey: XETMTRRGHPOVSP-NYVOZVTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(2S)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-{[(2S)-1-(benzyloxy)-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: N-[(1S)-3-Phenyl-1-[(phenylmethoxy)carbonyl]propyl]-L-alanyl-L-proline; (S)-1-[N-[3-Phenyl-1-[(phenylmethoxy)carbonyl]propyl]-L-alanyl]-L-proline; Enalaprilat Benzyl Ester

Database IDs

• CAS Number: 76391-33-8
• PubChem SID: 162262136
• PubChem CID: 22822716

CALCULATED PROPERTIES

• Acid pKa: 3.6713142
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6670681
• LogD (pH = 7.4): 0.31237468
• Log P: 1.9558822
• Molar Refractivity: 119.4386 cm^3
• Polarizability: 47.147243 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555380

Enalaprilat benzyl ester is an impurity of Enalaprilat maleate.

REFERENCES

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