ethyl (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: 177775
• Molecular Formular: C27H44O6
• Molecular Mass: 464.63466
• Monoisotopic Mass: 464.31378913
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)OCC)O)O)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCOC(=O)C[C@@H](C[C@@H](CC[C@H]1[C@@H](C)C=CC2=C[C@@H](C[C@@H]([C@H]12)OC(=O)C(CC)(C)C)C)O)O
• InChI: InChI=1S/C27H44O6/c1-7-27(5,6)26(31)33-23-14-17(3)13-19-10-9-18(4)22(25(19)23)12-11-20(28)15-21(29)16-24(30)32-8-2/h9-10,13,17-18,20-23,25,28-29H,7-8,11-12,14-16H2,1-6H3/t17-,18-,20+,21+,22-,23-,25-/m0/s1
• InChIKey: VVAUQJHCHXQKFR-MLKWKJRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (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: ethyl (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: (βR,δR,1S,2S,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-β,δ-dihydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid Ethyl Ester; Simvastatin Hydroxy Acid Ethyl Ester

Database IDs

• CAS Number: 864357-87-9
• PubChem SID: 164233685
• PubChem CID: 71752200

CALCULATED PROPERTIES

• Acid pKa: 14.726194
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.296432
• LogD (pH = 7.4): 4.296432
• Log P: 4.296432
• Molar Refractivity: 130.6933 cm^3
• Polarizability: 51.2911 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S485035

An impurity in Simvastatin (S485000).

REFERENCES

• Sankar, D. et al.: Asian J. Chem., 21, 4294 (2009)
• Vuletic, M. et al.: J. Pharmac. Biomed. Anal., 37, 715 (2009)