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

• ChemBase ID: 167995
• 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-BMSLDGIRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-2-{[(2R)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; (2Z)-but-2-enedioic acid
• IUPAC Traditional name: maleic acid; vasotec
• Synonyms: N-[(1R)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanyl-L-proline (2Z)-2-Butenedioate; (R)-1-[N-[1-(ethoxycarbonyl)-3-phenylpropyl]-L-alanyl]-L-proline Maleate; (R,S,S)-Enalapril Maleate

Database IDs

• PubChem SID: 162262127
• PubChem CID: 6435926

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: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E555245

The (R,S,S)-enantiomer of Enalapril maleate (E555250). An impurity of Enalapril.