methyl (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: 177771
• Molecular Formular: C26H42O6
• Molecular Mass: 450.60808
• Monoisotopic Mass: 450.29813906
• 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)OC)O)O)C)OC(=O)C(CC)(C)C
• Canonical SMILES: COC(=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/C26H42O6/c1-7-26(4,5)25(30)32-22-13-16(2)12-18-9-8-17(3)21(24(18)22)11-10-19(27)14-20(28)15-23(29)31-6/h8-9,12,16-17,19-22,24,27-28H,7,10-11,13-15H2,1-6H3/t16-,17-,19+,20+,21-,22-,24-/m0/s1
• InChIKey: ANVXHKJGHXLLPK-RVTXAWHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (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: methyl (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 Methyl Ester; Simvastatin Hydroxy Acid Methyl Ester

Database IDs

• CAS Number: 145576-26-7
• PubChem SID: 164233681
• PubChem CID: 11048644

CALCULATED PROPERTIES

• Acid pKa: 14.726204
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.939624
• LogD (pH = 7.4): 3.939624
• Log P: 3.939624
• Molar Refractivity: 125.9447 cm^3
• Polarizability: 49.452065 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Clear Colorless Thick Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - S485015

An impurity in Simvastatin (S485000) tablets.

REFERENCES

• Endo, A., et al.: J. Antibiot., 29, 1346 (1976)
• Hoffman, W., et al.: J. Med. Chem., 29, 849 (1976)
• Jemal, M., et al.: J. Pharm. Biomed. Anal., 23, 323 (1976)