(2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 160868
• Molecular Formular: C39H43FN2O11
• Molecular Mass: 734.7639232
• Monoisotopic Mass: 734.28508843
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OC(=O)C[C@@H](C[C@@H](CCn1c(c(c(c1C(C)C)C(=O)Nc1ccccc1)c1ccccc1)c1ccc(cc1)F)O)O
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)O[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)O)CCn1c(C(C)C)c(c(c1c1ccc(cc1)F)c1ccccc1)C(=O)Nc1ccccc1
• InChI: InChI=1S/C39H43FN2O11/c1-21(2)31-30(37(49)41-25-11-7-4-8-12-25)29(22-9-5-3-6-10-22)32(23-13-15-24(40)16-14-23)42(31)18-17-26(43)19-27(44)20-28(45)52-39-35(48)33(46)34(47)36(53-39)38(50)51/h3-16,21,26-27,33-36,39,43-44,46-48H,17-20H2,1-2H3,(H,41,49)(H,50,51)/t26-,27-,33-,34-,35+,36-,39+/m1/s1
• InChIKey: ZUTLXLYYUSGCQH-OIDPFDPZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6R)-6-{[(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-3,5-dihydroxyheptanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[(βR,δR)-2-(4-Fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoate] β-D-Glucopyranuronic Acid; Atorvastatin Acyl-β-D-glucuronide 70%, contains up to 30% lactone

Database IDs

• CAS Number: 463962-58-5
• PubChem SID: 162255003
• PubChem CID: 71313517

CALCULATED PROPERTIES

• Acid pKa: 3.247681
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): 1.2069682
• LogD (pH = 7.4): 0.002663404
• Log P: 3.4393532
• Molar Refractivity: 190.497 cm^3
• Polarizability: 75.88239 Å^3
• Polar Surface Area: 208.01 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 111-114°C

Safety Information

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

DETAILS

Toronto Research Chemicals - A791760

A metabolite of Atorvastatin.

REFERENCES

• Kantola, T., et al.: Eur. J. Clin. Pharmacol., 54, 851 (1998)
• Billecke, S., et al.: Drug Metab. Dispos., 28, 1335 (1998)
• Draganov, D., et al.: J. Biol. Chem., 275, 33435 (1998)
• Igel, M., et al.: Eur. J. Clin. Pharmacol., 57, 357 (1998)