(2S)-1-[(2R)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}(3,3,3-2H3)propanoyl]pyrrolidine-2-carboxylic acid

• ChemBase ID: 167997
• Molecular Formular: C20H28N2O5
• Molecular Mass: 376.44672
• Monoisotopic Mass: 376.19982201
• SMILES: c1cccc(c1)CC[C@H](N[C@@H](C(=O)N1CCC[C@H]1C(=O)O)C)C(=O)OCC
• Canonical SMILES: CCOC(=O)[C@@H](N[C@@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C20H28N2O5/c1-3-27-20(26)16(12-11-15-8-5-4-6-9-15)21-14(2)18(23)22-13-7-10-17(22)19(24)25/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25)/t14-,16+,17+/m1/s1
• InChIKey: GBXSMTUPTTWBMN-PVAVHDDUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2R)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}(3,3,3-^2H₃)propanoyl]pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[(2R)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}(3,3,3-^2H₃)propanoyl]pyrrolidine-2-carboxylic acid
• Synonyms: (S)-1-[N-[1-(Ethoxycarbonxyl)-3-phenylpropyl]-L-alanyl]-L-proline-d3; Enalapril-d3See E555252

Database IDs

• PubChem SID: 162262129
• PubChem CID: 71316327

CALCULATED PROPERTIES

• Acid pKa: 3.6713305
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.29928052
• LogD (pH = 7.4): -1.0552722
• Log P: 0.5877766
• Molar Refractivity: 99.5746 cm^3
• Polarizability: 39.423725 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555253

Labelled Enalapril, an antihypertensive. An angiotensin-converting enzyme (ACE) inhibitor.

REFERENCES

• Gross, M., et al.: J. Pharmacol. Exp. Ther., 216, 552 (1980)
• Gomez, H.J., et al.: J. Cardiovasc. Pharmacol., 15, Suppl. 3, S26-S29, (1980)
• MacFadyen, J., et al.: Clin. Pharmacokinet., 25, 274 (1980)
• Malini, P.L.: Adv. Ther., 10, 253 (1980)