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

• ChemBase ID: 159451
• Molecular Formular: C27H40O6
• Molecular Mass: 460.6029
• Monoisotopic Mass: 460.282489
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)OC(=O)C)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](OC(=O)C)CC(=O)O1)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C27H40O6/c1-7-27(5,6)26(30)33-23-13-16(2)12-19-9-8-17(3)22(25(19)23)11-10-20-14-21(31-18(4)28)15-24(29)32-20/h8-9,12,16-17,20-23,25H,7,10-11,13-15H2,1-6H3/t16-,17-,20+,21+,22-,23-,25-/m0/s1
• InChIKey: OHVWRJDVJRNCPE-BIKFJBPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(acetyloxy)-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-(acetyloxy)-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• Synonyms: 2,2-Dimethylbutanoic Acid (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-(Acetyloxy)tetrahydro-6-oxo-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl Ester; Simvastatin Acetate; 4'-Acetyl Simvastatin

Database IDs

• CAS Number: 145576-25-6
• PubChem SID: 162253586
• PubChem CID: 11812557

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.899327
• LogD (pH = 7.4): 4.899327
• Log P: 4.899327
• Molar Refractivity: 126.8349 cm^3
• Polarizability: 50.0936 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A187795

Simvastatin (S485000) impurity.

REFERENCES

• Shioi, A., et al.: J. Phys. Chem., 99, 4750 (1995)
• Wang, L., et al.: J. Pharm. Biomed. Anal., 21, 1243 (1995)
• Vuletic, M., et al.: J. Pharm. Biomed. Anal., 37, 715 (1995)