(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-bis(2H3)methylbutanoate

• ChemBase ID: 177768
• Molecular Formular: C25H38O5
• Molecular Mass: 418.56622
• Monoisotopic Mass: 418.27192432
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@@H](C1)O)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](O)CC(=O)O1)[C@H](C=C2)C)(C)C
• InChI: InChI=1S/C25H38O5/c1-6-25(4,5)24(28)30-21-12-15(2)11-17-8-7-16(3)20(23(17)21)10-9-19-13-18(26)14-22(27)29-19/h7-8,11,15-16,18-21,23,26H,6,9-10,12-14H2,1-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
• InChIKey: RYMZZMVNJRMUDD-HGQWONQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-bis(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-bis(^2H₃)methylbutanoate
• Synonyms: 2,2-(Dimethyl-d6)butanoic Acid(1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; (+)-Simvastatin-d6; Cholestat-d6; Lipex-d6; Novo-Simvastatin-d6; Simvotin-d6; Sinvacor-d6; Statin-d6; Zocor-d6; Zorced-d6; Simvastatin-d6

Database IDs

• PubChem SID: 164233678
• PubChem CID: 45040400

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.4582014
• LogD (pH = 7.4): 4.4582014
• Log P: 4.4582014
• Molar Refractivity: 117.6834 cm^3
• Polarizability: 46.25644 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMF; DMSO; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 117-120°C

Safety Information

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

DETAILS

Toronto Research Chemicals - S485002

Deuterated Simvastatin, a competitive inhibitor of HMG-CoA reductase. A synthetic analog of Lovastatin. Antilipemic.

REFERENCES

• Hoffman, W.F., et al.: J. Med. Chem., 29, 849 (1986)
• Mol, M.J., et al.: Lancet, 2, 936 (1986)