(6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3-hydroxy-5-oxohept-6-enoic acid

• ChemBase ID: 172070
• Molecular Formular: C24H24FNO4
• Molecular Mass: 409.4500632
• Monoisotopic Mass: 409.16893647
• SMILES: c1cccc2c1c(c(n2C(C)C)/C=C/C(=O)CC(CC(=O)O)O)c1ccc(cc1)F
• Canonical SMILES: OC(=O)CC(CC(=O)/C=C/c1c(c2ccc(cc2)F)c2c(n1C(C)C)cccc2)O
• InChI: InChI=1S/C24H24FNO4/c1-15(2)26-21-6-4-3-5-20(21)24(16-7-9-17(25)10-8-16)22(26)12-11-18(27)13-19(28)14-23(29)30/h3-12,15,19,28H,13-14H2,1-2H3,(H,29,30)/b12-11+
• InChIKey: FSIBOMHNSMFWBF-VAWYXSNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E)-7-[3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl]-3-hydroxy-5-oxohept-6-enoic acid
• IUPAC Traditional name: (6E)-7-[3-(4-fluorophenyl)-1-isopropylindol-2-yl]-3-hydroxy-5-oxohept-6-enoic acid
• Synonyms: (E)-(+/-)-7-[3-(4-Fluorophenyl)-1-(methylethyl)-1H-indol-2-yl]-3-hydroxy-5-oxo-6-heptenoic Acid; Fluvastatin Impurity; rac 5-Keto Fluvastatin

Database IDs

• CAS Number: 1160169-39-0
• PubChem SID: 164227980
• PubChem CID: 23112881

CALCULATED PROPERTIES

• Acid pKa: 4.444051
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.3749032
• LogD (pH = 7.4): 1.6123297
• Log P: 4.465989
• Molar Refractivity: 113.8475 cm^3
• Polarizability: 45.493576 Å^3
• Polar Surface Area: 79.53 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K188905

Fluvastatin impurity.

REFERENCES

• Kathawala, F.G., et al.: Med. Res. Reviews, 11, 121 (1991)