(2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(2H5)phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; (2Z)-but-2-enedioic acid

• ChemBase ID: 167996
• Molecular Formular: C24H32N2O9
• Molecular Mass: 492.51888
• Monoisotopic Mass: 492.21078061
• SMILES: C(=C\C(=O)O)\C(=O)O.C1C[C@H](N(C1)C(=O)[C@@H](N[C@@H](CCc1ccccc1)C(=O)OCC)C)C(=O)O
• Canonical SMILES: OC(=O)/C=C\C(=O)O.CCOC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1
• InChI: InChI=1S/C20H28N2O5.C4H4O4/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;5-3(6)1-2-4(7)8/h4-6,8-9,14,16-17,21H,3,7,10-13H2,1-2H3,(H,24,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,16-,17-;/m0./s1
• InChIKey: OYFJQPXVCSSHAI-QFPUQLAESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: (2S)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-(^2H₅)phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; maleic acid
• Synonyms: N-[(1S)-1-(Ethoxycarbonyl)-3-(phenyl-d5)propyl]-L-alanyl-L-proline (2Z)-2-Butenedioate; Acapril-d5; Acetensil-d5; Alphrin-d5; Amprace-d5; Enaloc-d5; Enapren-d5; Enapril-d5; Enaprin-d5; Glioten-d5; Hipoartel-d5; Hytrol-d5; Innovace-d5; Innovade-d5; Lapril-d5; Lotrial-d5; MK 421-d5; Reniten-d5; Renivace-d5; Tenace-d5; Unaril-d5; Vasotec-d5; Xanef-d5; (S,S,S)-Enalapril-d5 Maleate Salt

Database IDs

• PubChem SID: 162262128
• PubChem CID: 71316326

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: 39.44501 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 34-36°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E555252

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)