(4R,6S)-6-[(E)-2-[2-(2H5)cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one

• ChemBase ID: 176806
• Molecular Formular: C25H22FNO3
• Molecular Mass: 403.4454832
• Monoisotopic Mass: 403.15837179
• SMILES: c12c(c(c(c(n1)C1CC1)/C=C/[C@@H]1C[C@@H](O)CC(=O)O1)c1ccc(cc1)F)cccc2
• Canonical SMILES: O[C@H]1CC(=O)O[C@@H](C1)/C=C/c1c(nc2c(c1c1ccc(cc1)F)cccc2)C1CC1
• InChI: InChI=1S/C25H22FNO3/c26-17-9-7-15(8-10-17)24-20-3-1-2-4-22(20)27-25(16-5-6-16)21(24)12-11-19-13-18(28)14-23(29)30-19/h1-4,7-12,16,18-19,28H,5-6,13-14H2/b12-11+/t18-,19-/m1/s1
• InChIKey: XJVKVAFYQRWVAJ-MCBHFWOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6S)-6-[(E)-2-[2-(^2H₅)cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one
• IUPAC Traditional name: (4R,6S)-6-[(E)-2-[2-(^2H₅)cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]ethenyl]-4-hydroxyoxan-2-one
• Synonyms: (4R,6S)-6-[(1E)-2-[2-(Cyclopropyl-d5)-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-one; [4R-[4α,6β(E)]]-6-[2-[2-(Cyclopropyl-d5)-4-(4-fluorophenyl)-3-quinolinyl]ethenyl]tetrahydro-4-hydroxy-2H-pyran-2-one; NK 104-d5; NK 104-d5 (lactone); Nisvastatin-d5; P 872441-d5; Pitavastatin-d5 Lactone

Database IDs

• PubChem SID: 164232716
• PubChem CID: 71751708

CALCULATED PROPERTIES

• Acid pKa: 14.903429
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.475889
• LogD (pH = 7.4): 4.5424976
• Log P: 4.543419
• Molar Refractivity: 112.247 cm^3
• Polarizability: 45.725452 Å^3
• Polar Surface Area: 59.42 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 72-75°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P531022

A labelled metabolite of Pitavastatin. Recent studies have shown that conversion between acid and lactone forms occurs in the body, drug-drug interaction should be considered on both acid and lactone forms. The inhibitory effects of statins on CYP metabol

REFERENCES

• Wang, J., et al.: Drug Metab. Dispos., 30, 1352 (2002)
• Yamada, I., et al.: Xenobiotica, 33, 789 (2002)
• Fujino, H., et al.: Xenobiotica, 34, 961 (2002)
• Ando, H., et al.: Br. J. Clin. Pharmacol., 60, 494 (2002)