sodium (2R,4S)-4-cyclohexyl-1-{2-[(R)-[(1S)-2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylate

• ChemBase ID: 169452
• Molecular Formular: C30H45NNaO7P
• Molecular Mass: 585.644331
• Monoisotopic Mass: 585.2831337
• SMILES: c1ccccc1CCCC[P@](=O)(CC(=O)N1[C@H](C[C@H](C1)C1CCCCC1)C(=O)[O-])O[C@H](OC(=O)CC)C(C)C.[Na+]
• Canonical SMILES: CCC(=O)O[C@H](C(C)C)O[P@@](=O)(CC(=O)N1C[C@@H](C[C@@H]1C(=O)[O-])C1CCCCC1)CCCCc1ccccc1.[Na+]
• InChI: InChI=1S/C30H46NO7P.Na/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24;/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35);/q;+1/p-1/t25-,26-,30+,39-;/m1./s1
• InChIKey: TVTJZMHAIQQZTL-ZFNUZWRFSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,4S)-4-cyclohexyl-1-{2-[(R)-[(1S)-2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylate
• IUPAC Traditional name: sodium (2R,4S)-4-cyclohexyl-1-{2-[(R)-(1S)-2-methyl-1-(propanoyloxy)propoxy(4-phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylate
• Synonyms: (4S)-4-Cyclohexyl-1-[[(R)-[(1S)-2-methyl-1-(1-oxopropoxy)propoxy](4-phenylbutyl)phosphinyl]acetyl]-D-proline Sodium Salt; Fosinopril Impurity B; (4S)-4-Cyclohexyl-1-[(R)-[(S)-1-hydroxy-2-methylpropoxy](4-phenylbutyl)phosphinyl]acetyl-D-proline Propionate Sodium Salt; (2R,4S)-Fosinopril Sodium Salt

Database IDs

• PubChem SID: 162263584
• PubChem CID: 71316976

CALCULATED PROPERTIES

• Acid pKa: 3.870143
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.8497143
• LogD (pH = 7.4): 2.1873627
• Log P: 5.4858
• Molar Refractivity: 159.9567 cm^3
• Polarizability: 59.37905 Å^3
• Polar Surface Area: 113.04 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F727830

An epimeric impurity of the ACE inhibitor Fosinopril (F727800)