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

• ChemBase ID: 171304
• Molecular Formular: C25H38O6
• Molecular Mass: 434.56562
• Monoisotopic Mass: 434.26683894
• SMILES: [C@@H]1(C[C@H]([C@@H](C2=C1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@@H](C1)O)O)C)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)[C@@H](C2=C1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@@H](C)C=C2)O)(C)C
• InChI: InChI=1S/C25H38O6/c1-6-25(4,5)24(29)31-20-11-15(3)23(28)19-9-7-14(2)18(22(19)20)10-8-17-12-16(26)13-21(27)30-17/h7,9,14-18,20,23,26,28H,6,8,10-13H2,1-5H3/t14-,15+,16+,17+,18-,20-,23-/m0/s1
• InChIKey: PHYROLUQFDDXMM-LDTLXGEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,4S,7S,8S)-4-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,7,8-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• IUPAC Traditional name: (1S,3R,4S,7S,8S)-4-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,7,8-hexahydronaphthalen-1-yl 2,2-dimethylbutanoate
• Synonyms: 2,2-Dimethylbutanoic Acid [1S-[1α,3α,4β,7β,8β(2S*,4S*)]]-1,2,3,4,7,8-Hexahydro-4-hydroxy-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester; 5'(S)-Hydroxy SimvastatinDISCONTINUED

Database IDs

• CAS Number: 149949-05-3
• PubChem SID: 164227214
• PubChem CID: 21763233

CALCULATED PROPERTIES

• Acid pKa: 14.19993
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.33964
• LogD (pH = 7.4): 3.3396397
• Log P: 3.33964
• Molar Refractivity: 118.7783 cm^3
• Polarizability: 46.89067 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H953520

A derivative of Simvastatin. An isomer of 3’(S)-Hydroxy 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)