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

• ChemBase ID: 167801
• Molecular Formular: C25H40O7
• Molecular Mass: 452.5809
• Monoisotopic Mass: 452.27740362
• SMILES: [C@@H]1(C[C@H](C(C2=CC([C@@H]([C@@H]([C@@H]12)CC[C@H]1OC(=O)C[C@@H](C1)O)C)O)O)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)C(C2=CC([C@@H]([C@@H]([C@@H]12)CC[C@@H]1C[C@@H](O)CC(=O)O1)C)O)O)(C)C
• InChI: InChI=1S/C25H40O7/c1-6-25(4,5)24(30)32-20-9-13(2)23(29)18-12-19(27)14(3)17(22(18)20)8-7-16-10-15(26)11-21(28)31-16/h12-17,19-20,22-23,26-27,29H,6-11H2,1-5H3/t13-,14-,15-,16-,17+,19?,20+,22-,23?/m1/s1
• InChIKey: MRCKOKWQDZYFLT-IHHACARCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7R,8S,8aR)-4,6-dihydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl 2,2-bis(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,3R,7R,8S,8aR)-4,6-dihydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,6,7,8,8a-octahydronaphthalen-1-yl 2,2-bis(^2H₃)methylbutanoate
• Synonyms: [1S-[1α,3α,4β,6α,7β,8β(2S*,4S*),8aβ]]-Butanoic Acid 2,2-(Dimethyl-d6)-1,2,3,4,6,7,8,8a-octahydro-4,6-dihydroxy-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester; 3',5'-Dihydrodiol Simvastatin-d6(Mixture of Diastereomers)

Database IDs

• PubChem SID: 162261934
• PubChem CID: 71316235

CALCULATED PROPERTIES

• Acid pKa: 14.066692
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.514408
• LogD (pH = 7.4): 2.514408
• Log P: 2.514408
• Molar Refractivity: 119.4438 cm^3
• Polarizability: 47.780605 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452692

A labelled metabolite of Simvastatin (S485000).

REFERENCES

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