sodium (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-(2H5)phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylate

• ChemBase ID: 168003
• Molecular Formular: C18H23N2NaO5
• Molecular Mass: 370.37539
• Monoisotopic Mass: 370.15046613
• SMILES: C1C[C@H](N(C1)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)O)C)C(=O)[O-].[Na+]
• Canonical SMILES: OC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)[O-])C)CCc1ccccc1.[Na+]
• InChI: InChI=1S/C18H24N2O5.Na/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);/q;+1/p-1/t12-,14-,15-;/m0./s1
• InChIKey: DUDLNVUQNQFAHG-XJPBFQKESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylate
• IUPAC Traditional name: sodium (2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-(^2H₅)phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylate
• Synonyms: N-[(1S)-1-(Carboxy)-(3-phenyl-d5)propyl]-L-alanyl]-L-proline Dihydrate; Enalaprilic Acid-d5; MK-422-d5; Vasotec IV-d5; Enalaprilat-d5 Sodium Salt

Database IDs

• CAS Number: 1356922-29-6
• PubChem SID: 162262135
• PubChem CID: 45039129

CALCULATED PROPERTIES

• Acid pKa: 3.132935
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -2.2588751
• LogD (pH = 7.4): -4.0126777
• Log P: -1.0502586
• Molar Refractivity: 100.894 cm^3
• Polarizability: 35.41851 Å^3
• Polar Surface Area: 109.77 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 166-168°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - E555377

Labelled 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)