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

• ChemBase ID: 155575
• Molecular Formular: C24H32N2O9
• Molecular Mass: 492.51888
• Monoisotopic Mass: 492.21078061
• SMILES: CCOC(=O)[C@H](CCc1ccccc1)N[C@@H](C)C(=O)N1CCC[C@@H]1C(=O)O.C(=C\C(=O)O)/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)/t14-,16-,17+;/m0./s1
• InChIKey: OYFJQPXVCSSHAI-SZIOFJSKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; but-2-enedioic acid
• IUPAC Traditional name: (2R)-1-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]pyrrolidine-2-carboxylic acid; butenedioic acid
• Synonyms: (S)-N-[1-(Ethoxycarbonyl)-3-phenylpropyl]-Ala-Pro maleate salt; Enalapril maleate salt

Database IDs

• CAS Number: 76095-16-4
• EC Number: 278-375-7
• MDL Number: MFCD00133304
• PubChem SID: 162249713; 24894639
• PubChem CID: 71312158

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

PROPERTIES

Physical Property

• Solubility: methanol: ≥50 mg/mL, clear, colorless to yellow
• Apperance: white to off-white powder

Safety Information

• RTECS: TW3666000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC)
• Empirical Formula (Hill Notation): C20H28N2O5 · C4H4O4

DETAILS

Sigma Aldrich - E6888

Biochem/physiol Actions
A long-acting angiotensin-converting enzyme inhibitor.