(2R,4R)-2-{2-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-6-oxooxan-4-yl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 177770
• Molecular Formular: C50H76O10
• Molecular Mass: 837.13244
• Monoisotopic Mass: 836.54384863
• SMILES: C1[C@H](C=C2[C@H]([C@H]1OC(=O)C(C)(C)CC)[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)O[C@@H]1C[C@H](OC(=O)C1)CC[C@@H]1[C@@H]2C(=C[C@@H](C[C@@H]2OC(=O)C(C)(C)CC)C)C=C[C@@H]1C)O)O)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)O[C@@H]1C[C@@H](CC[C@H]3[C@@H](C)C=CC4=C[C@@H](C[C@@H]([C@H]34)OC(=O)C(CC)(C)C)C)OC(=O)C1)O)O)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C50H76O10/c1-11-49(7,8)47(55)59-41-23-29(3)21-33-15-13-31(5)39(45(33)41)19-17-35(51)25-36(52)26-43(53)58-38-27-37(57-44(54)28-38)18-20-40-32(6)14-16-34-22-30(4)24-42(46(34)40)60-48(56)50(9,10)12-2/h13-16,21-22,29-32,35-42,45-46,51-52H,11-12,17-20,23-28H2,1-10H3/t29-,30-,31-,32-,35+,36+,37+,38+,39-,40-,41-,42-,45-,46-/m0/s1
• InChIKey: GUEULYYYHDURDF-CWZAOXTASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R)-2-{2-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-6-oxooxan-4-yl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: (2R,4R)-2-{2-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-6-oxooxan-4-yl (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: Simvastatin Impurity D; Simvastatin Dimer Impurity

Database IDs

• CAS Number: 476305-24-5
• PubChem SID: 164233680
• PubChem CID: 46782920

CALCULATED PROPERTIES

• Acid pKa: 14.726184
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 8.916403
• LogD (pH = 7.4): 8.916403
• Log P: 8.916403
• Molar Refractivity: 235.3668 cm^3
• Polarizability: 92.51288 Å^3
• Polar Surface Area: 145.66 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 170-180°C

Safety Information

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

DETAILS

Toronto Research Chemicals - S485010

An impurity of Simvastatin (Dimer).

REFERENCES

• Wang, L., et al.: J. Pharm. Biomed. Anal., 21, 1243 (2000)
• Srinivasu, M., et al.: J. Pharm. Biomed. Anal., 29, 715 (2000)
• Vuletic, M., et al.: J. Pharm. Biomed. Anal., 37, 715 (2000)