sodium (2R,4S)-4-cyclohexyl-1-(2-{hydroxy[4-(2H5)phenylbutyl]phosphoryl}acetyl)pyrrolidine-2-carboxylate

• ChemBase ID: 169449
• Molecular Formular: C23H33NNaO5P
• Molecular Mass: 457.475351
• Monoisotopic Mass: 457.19940407
• SMILES: c1ccccc1CCCCP(=O)(CC(=O)N1[C@H](C[C@H](C1)C1CCCCC1)C(=O)[O-])O.[Na+]
• Canonical SMILES: O=C(N1C[C@@H](C[C@@H]1C(=O)[O-])C1CCCCC1)CP(=O)(CCCCc1ccccc1)O.[Na+]
• InChI: InChI=1S/C23H34NO5P.Na/c25-22(17-30(28,29)14-8-7-11-18-9-3-1-4-10-18)24-16-20(15-21(24)23(26)27)19-12-5-2-6-13-19;/h1,3-4,9-10,19-21H,2,5-8,11-17H2,(H,26,27)(H,28,29);/q;+1/p-1/t20-,21-;/m1./s1
• InChIKey: ZPIVICMRZRGSIT-MUCZFFFMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,4S)-4-cyclohexyl-1-(2-{hydroxy[4-(^2H₅)phenylbutyl]phosphoryl}acetyl)pyrrolidine-2-carboxylate
• IUPAC Traditional name: sodium (2R,4S)-4-cyclohexyl-1-{2-[hydroxy(4-(^2H₅)phenylbutyl)phosphoryl]acetyl}pyrrolidine-2-carboxylate
• Synonyms: (4S)-4-Cyclohexyl-1-[2-[hydroxy(4-phenyl-d5-butyl)phosphinyl]acetyl]-L-proline Sodium Salt; Fosfenopril-d5 Sodium Salt; Fosinoprilic Acid-d5 Sodium Salt; SQ 27519-d5 Sodium Salt; Fosinoprilat-d5 Sodium Salt

Database IDs

• PubChem SID: 162263581
• PubChem CID: 71316971

CALCULATED PROPERTIES

• Acid pKa: 1.7555045
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.594025
• LogD (pH = 7.4): -2.3612165
• Log P: 2.992
• Molar Refractivity: 126.8667 cm^3
• Polarizability: 45.48311 Å^3
• Polar Surface Area: 97.74 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - F727812

A labelled metabolite of Fosinopril, a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor.

REFERENCES

• Petrillo, E.W., et al.: Med. Res. Rev., 2, 1 (1982)