disodium (2R,4S)-4-cyclohexyl-1-{2-[(4-phenylbutyl)phosphinato]acetyl}pyrrolidine-2-carboxylate

• ChemBase ID: 169448
• Molecular Formular: C23H32NNa2O5P
• Molecular Mass: 479.457181
• Monoisotopic Mass: 479.18134832
• SMILES: c1ccccc1CCCCP(=O)(CC(=O)N1[C@H](C[C@H](C1)C1CCCCC1)C(=O)[O-])[O-].[Na+].[Na+]
• Canonical SMILES: O=C(N1C[C@@H](C[C@@H]1C(=O)[O-])C1CCCCC1)CP(=O)(CCCCc1ccccc1)[O-].[Na+].[Na+]
• InChI: InChI=1S/C23H34NO5P.2Na/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;2*+1/p-2/t20-,21-;;/m1../s1
• InChIKey: FQYBAGQKPPILDV-OXIQQVKJSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (2R,4S)-4-cyclohexyl-1-{2-[(4-phenylbutyl)phosphinato]acetyl}pyrrolidine-2-carboxylate
• IUPAC Traditional name: disodium (2R,4S)-4-cyclohexyl-1-[2-(4-phenylbutylphosphinato)acetyl]pyrrolidine-2-carboxylate
• Synonyms: (4S)-4-Cyclohexyl-1-[2-[hydroxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline Disodium Salt; Fosfenopril Disodium Salt; Fosinoprilic Acid Disodium Salt; SQ 27519 Disodium Salt; Fosinoprilat Disodium Salt

Database IDs

• CAS Number: 95399-71-6
• PubChem SID: 162263580
• PubChem CID: 71316969

CALCULATED PROPERTIES

• Acid pKa: 1.7555045
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.594025
• LogD (pH = 7.4): -2.3612165
• Log P: 2.992
• Molar Refractivity: 125.745 cm^3
• Polarizability: 45.35072 Å^3
• Polar Surface Area: 100.57 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >300°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F727810

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

REFERENCES

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