5-(4-fluorophenyl)-1-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-N,4-diphenyl-2-(propan-2-yl)-1H-pyrrole-3-carboxamide

• ChemBase ID: 160743
• Molecular Formular: C33H33FN2O4
• Molecular Mass: 540.6245232
• Monoisotopic Mass: 540.24243577
• SMILES: c1(c(c(n(c1C(C)C)CC[C@@H]1C[C@H](CC(=O)O1)O)c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
• Canonical SMILES: O[C@@H]1C[C@@H](CCn2c(C(C)C)c(c(c2c2ccc(cc2)F)c2ccccc2)C(=O)Nc2ccccc2)OC(=O)C1
• InChI: InChI=1S/C33H33FN2O4/c1-21(2)31-30(33(39)35-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(34)16-14-23)36(31)18-17-27-19-26(37)20-28(38)40-27/h3-16,21,26-27,37H,17-20H2,1-2H3,(H,35,39)/t26-,27-/m1/s1
• InChIKey: OUCSEDFVYPBLLF-KAYWLYCHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(4-fluorophenyl)-1-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-N,4-diphenyl-2-(propan-2-yl)-1H-pyrrole-3-carboxamide
• IUPAC Traditional name: 5-(4-fluorophenyl)-1-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-2-isopropyl-N,4-diphenylpyrrole-3-carboxamide
• Synonyms: 5-(4-Fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1H-pyrrole-3-carboxamide; Atorvastatin δ-Lactone; Atorvastatin Lactone

Database IDs

• CAS Number: 125995-03-1
• PubChem SID: 162254878
• PubChem CID: 6483036

CALCULATED PROPERTIES

• Acid pKa: 11.824506
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 6.0516176
• LogD (pH = 7.4): 6.0516024
• Log P: 6.051618
• Molar Refractivity: 154.7062 cm^3
• Polarizability: 61.189014 Å^3
• Polar Surface Area: 80.56 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Ethyl Acetate; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 103-106°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A791780

Atorvastatin intermediate as inhibitor of MAP kinase and/or HMG-CoA reductase for the treatment of inflammation.

REFERENCES

• Boyd, R., et al.: J. Clin. Pharmacol., 40, 91, (2000)
• Bogman, K., et al.: Br. J. Pharmacol., 132, 1183 (2000)
• Backman, J., et al.: Clin. Pharmacol. Ther., 72, 685 (2000)
• Kalvass, J., et al.: Drug Metab. Dispos., 35, 455(2000)