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

• ChemBase ID: 171301
• Molecular Formular: C25H38O6
• Molecular Mass: 434.56562
• Monoisotopic Mass: 434.26683894
• SMILES: [C@@H]1(CC(=CC2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@H]1OC(=O)C[C@@H](C1)O)C)O)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1CC(=CC2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@@H]1C[C@@H](O)CC(=O)O1)C)O)C)(C)C
• InChI: InChI=1S/C25H38O6/c1-6-25(4,5)24(29)31-21-10-14(2)9-16-11-20(27)15(3)19(23(16)21)8-7-18-12-17(26)13-22(28)30-18/h9,11,15,17-21,23,26-27H,6-8,10,12-13H2,1-5H3/t15-,17-,18-,19+,20-,21+,23+/m1/s1
• InChIKey: ZHTMJJNBYMYMRV-VVSCFXOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,6S,7R,8S,8aR)-6-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• IUPAC Traditional name: (1S,6S,7R,8S,8aR)-6-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• Synonyms: 2,2-Dimethylbutanoic Acid [1S-[1α,6α,7β,8β(2S*,4S*),8aβ]]-1,2,6,7,8,8a-Hexahydro-6-hydroxy-3,7-dimethyl)-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester; 3'(S)-Hydroxy SimvastatinDISCONTINUED

Database IDs

• CAS Number: 133645-46-2
• PubChem SID: 164227211
• PubChem CID: 21728613

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.261686
• LogD (pH = 7.4): 3.261686
• Log P: 3.261686
• Molar Refractivity: 118.8553 cm^3
• Polarizability: 46.89067 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true
• Acid pKa: 14.914537

DETAILS

Toronto Research Chemicals - H953500

A derivative of Simvastatin.

REFERENCES

• Vyas, K.P., et al.: Drug Metab. Dispos., 18, 203 (1990)
• Nakamura, T., et al.: Xenobiotica, 21, 277 (1990)
• Cheng, H., et al.: Drug Metab. Dispos., 22, 139 (1990)