(4R,6S)-6-[(E)-2-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]ethenyl]-4-hydroxyoxan-2-one

• ChemBase ID: 169309
• Molecular Formular: C24H24FNO3
• Molecular Mass: 393.4506632
• Monoisotopic Mass: 393.17402185
• SMILES: c1cccc2c1c(c(n2C(C)C)/C=C/[C@@H]1C[C@H](CC(=O)O1)O)c1ccc(cc1)F
• Canonical SMILES: O[C@H]1CC(=O)O[C@@H](C1)/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2
• InChI: InChI=1S/C24H24FNO3/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-19-13-18(27)14-23(28)29-19/h3-12,15,18-19,27H,13-14H2,1-2H3/b12-11+/t18-,19-/m1/s1
• InChIKey: VPXDEUFAXJFWBG-MCBHFWOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6S)-6-[(E)-2-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]ethenyl]-4-hydroxyoxan-2-one
• IUPAC Traditional name: (4R,6S)-6-[(E)-2-[3-(4-fluorophenyl)-1-isopropylindol-2-yl]ethenyl]-4-hydroxyoxan-2-one
• Synonyms: Fluindostatin; XU 62-320; Lescol; Lipaxan; Primexin; (4R,6S)-6-[(1E)-2-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]ethenyl]tetrahydro-4-hydroxy-2H-Pyran-2-one; Fluvastatin Lactone

Database IDs

• CAS Number: 94061-83-3
• PubChem SID: 162263441
• PubChem CID: 29980473

CALCULATED PROPERTIES

• Acid pKa: 14.903428
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.4904203
• LogD (pH = 7.4): 4.4904203
• Log P: 4.4904203
• Molar Refractivity: 111.3631 cm^3
• Polarizability: 44.96492 Å^3
• Polar Surface Area: 51.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 160-162°C

Safety Information

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

DETAILS

Toronto Research Chemicals - F601255

A synthetic HMG-CoA reductase inhibitor.

REFERENCES

• Yuan, J., et al.: Atherosclerosis, 87, 147 (1991)
• Tse, F.L.S., et al.: J. Clin. Pharmacol., 32, 630 (1991)
• Dain, J.G., et al.: Drug Metab. Disposit., 21, 567 (1991)