(2R,4S)-4-cyclohexyl-1-(2-{hydroxy[4-(4-hydroxyphenyl)butyl]phosphoryl}acetyl)pyrrolidine-2-carboxylic acid

• ChemBase ID: 170594
• Molecular Formular: C23H34NO6P
• Molecular Mass: 451.492921
• Monoisotopic Mass: 451.21237444
• SMILES: c1cc(ccc1CCCCP(=O)(CC(=O)N1[C@H](C[C@H](C1)C1CCCCC1)C(=O)O)O)O
• Canonical SMILES: OC(=O)[C@H]1C[C@H](CN1C(=O)CP(=O)(CCCCc1ccc(cc1)O)O)C1CCCCC1
• InChI: InChI=1S/C23H34NO6P/c25-20-11-9-17(10-12-20)6-4-5-13-31(29,30)16-22(26)24-15-19(14-21(24)23(27)28)18-7-2-1-3-8-18/h9-12,18-19,21,25H,1-8,13-16H2,(H,27,28)(H,29,30)/t19-,21-/m1/s1
• InChIKey: DVLCIJJQVXIPRO-TZIWHRDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S)-4-cyclohexyl-1-(2-{hydroxy[4-(4-hydroxyphenyl)butyl]phosphoryl}acetyl)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R,4S)-4-cyclohexyl-1-{2-[hydroxy(4-(4-hydroxyphenyl)butyl)phosphoryl]acetyl}pyrrolidine-2-carboxylic acid
• Synonyms: trans-4-Cyclohexyl-1-[[hydroxy[4-(4-hydroxyphenyl)butyl]phosphinyl]acetyl]-L-proline; 4-Hydroxy Fosinoprilat

Database IDs

• CAS Number: 113411-10-2
• PubChem SID: 164226504
• PubChem CID: 71749047

CALCULATED PROPERTIES

• Acid pKa: 1.7555045
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.8784318
• LogD (pH = 7.4): -2.646153
• Log P: 2.7076
• Molar Refractivity: 118.0105 cm^3
• Polarizability: 46.21228 Å^3
• Polar Surface Area: 115.14 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

REFERENCES

• Singhvi, S.M., et al.: Br. J. Clin. Pharmacol., 25, 9 (1988)