(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-dimethylbut-3-enoate

• ChemBase ID: 166247
• Molecular Formular: C25H36O5
• Molecular Mass: 416.55034
• Monoisotopic Mass: 416.25627425
• 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(C=C)(C)C
• Canonical SMILES: C=CC(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/C25H36O5/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/h6-8,11,15-16,18-21,23,26H,1,9-10,12-14H2,2-5H3/t15-,16-,18+,19+,20-,21-,23-/m0/s1
• InChIKey: PHAXMMMKRGSDIV-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-dimethylbut-3-enoate
• 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-dimethylbut-3-enoate
• Synonyms: 2''-Desethyl-2''-vinyl Simvastatin

Database IDs

• PubChem SID: 162260380
• PubChem CID: 71315645

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.1542134
• LogD (pH = 7.4): 4.1542134
• Log P: 4.1542134
• Molar Refractivity: 117.7275 cm^3
• Polarizability: 46.013737 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D289830

Simvastatin (S485000) impurity.