(2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 168002
• Molecular Formular: C18H24N2O5
• Molecular Mass: 348.39356
• Monoisotopic Mass: 348.16852188
• SMILES: C1C[C@H](N(C1)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)O)C)C(=O)O
• Canonical SMILES: OC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C18H24N2O5/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25)/t12-,14-,15-/m0/s1
• InChIKey: LZFZMUMEGBBDTC-QEJZJMRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: enalaprilat
• Synonyms: N-[(1S)-1-(Carboxy)-3-phenylpropyl]-L-alanyl]-L-proline Dihydrate; Enalaprilic Acid Dihydrate; MK-422 Dihydrate; Vasotec IV Dihydrate; Enalaprilat Dihydrate

Database IDs

• CAS Number: 84680-54-6
• PubChem SID: 162262134
• PubChem CID: 5462501

CALCULATED PROPERTIES

• Acid pKa: 3.132935
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.2588751
• LogD (pH = 7.4): -4.0126777
• Log P: -1.0502586
• Molar Refractivity: 90.0569 cm^3
• Polarizability: 35.51059 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Methanol; Water
• Apperance: White Solid
• Melting Point: 151-159°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E555375

Active metabolite of Enalapril. A nonsulfhydryl dipeptide angiotensin converting enzyme (ACE) inhibitor.

REFERENCES

• Tocco, D.J., et al.: Drug Metab. Dispos., 10, 15 (1982)
• Cohen, M.L., et al.: J. Pharmacol. Exp. Ther., 226, 192 (1982)
• DiPette, D.J., et al.: Clin. Pharm. Ther., 38, 199 (1985)