methyl (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate

• ChemBase ID: 169312
• Molecular Formular: C25H28FNO4
• Molecular Mass: 425.4925232
• Monoisotopic Mass: 425.2002366
• SMILES: c1ccc2c(c1)c(c(n2C(C)C)/C=C/[C@H](C[C@H](CC(=O)OC)O)O)c1ccc(cc1)F
• Canonical SMILES: COC(=O)C[C@@H](C[C@@H](/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2)O)O
• InChI: InChI=1S/C25H28FNO4/c1-16(2)27-22-7-5-4-6-21(22)25(17-8-10-18(26)11-9-17)23(27)13-12-19(28)14-20(29)15-24(30)31-3/h4-13,16,19-20,28-29H,14-15H2,1-3H3/b13-12+/t19-,20-/m1/s1
• InChIKey: BOCZYIUKFAQNLG-OKLSWEBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3,5-dihydroxyhept-6-enoate
• IUPAC Traditional name: methyl (3R,5S,6E)-7-[3-(4-fluorophenyl)-1-isopropylindol-2-yl]-3,5-dihydroxyhept-6-enoate
• Synonyms: (3R,5S,6E)-rel-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic Acid Methyl Ester; [R*,S*-(E)]-(+/-)-7-[3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indol-2-yl]-3,5-dihydroxy-6-heptenoic Acid Methyl Ester; Fluvastatin Methyl Ester

Database IDs

• CAS Number: 93957-53-0
• PubChem SID: 162263444
• PubChem CID: 40492830

CALCULATED PROPERTIES

• Acid pKa: 14.5413
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.9718432
• LogD (pH = 7.4): 3.971843
• Log P: 3.9718432
• Molar Refractivity: 119.6244 cm^3
• Polarizability: 48.143566 Å^3
• Polar Surface Area: 71.69 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F601275

An intermediate for the selective synthesis of Fluvastatin (F601250).

REFERENCES

• Noguchi, N., et al.: Biochim. Biophys. Acta, 1213, 176 (1994)
• Mitani, H., et al.: Br. J. Pharmacol., 119, 1269 (1994)
• Yamamoto, A., et al.: Eur. J. Pharm., 361, 143 (1994)