(1S,3S,7S,8S,8aR)-3-hydroperoxy-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-dimethylbutanoate

• ChemBase ID: 171139
• Molecular Formular: C25H38O7
• Molecular Mass: 450.56502
• Monoisotopic Mass: 450.26175356
• SMILES: [C@@H]1(C[C@](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@@H](C1)O)(C)OO)OC(=O)C(CC)(C)C
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@](C)(OO)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/C25H38O7/c1-6-24(3,4)23(28)31-20-14-25(5,32-29)13-16-8-7-15(2)19(22(16)20)10-9-18-11-17(26)12-21(27)30-18/h7-8,13,15,17-20,22,26,29H,6,9-12,14H2,1-5H3/t15-,17+,18+,19-,20-,22-,25+/m0/s1
• InChIKey: FOGQBCWWWLNSOK-ZEUMIXTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7S,8S,8aR)-3-hydroperoxy-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-dimethylbutanoate
• IUPAC Traditional name: (1S,3S,7S,8S,8aR)-3-hydroperoxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-2,7,8,8a-tetrahydro-1H-naphthalen-1-yl 2,2-dimethylbutanoate
• Synonyms: 2,2-Dimethylbutanoic Acid (1S,3S,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3-hydroperoxy-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; 3(S)-Hydroperoxy Simvastatin

Database IDs

• CAS Number: 1092716-44-3
• PubChem SID: 164227049
• PubChem CID: 71749274

CALCULATED PROPERTIES

• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• Acid pKa: 11.698172
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.5974889
• LogD (pH = 7.4): 3.5974674
• Log P: 3.597489
• Molar Refractivity: 120.5951 cm^3
• Polarizability: 47.60519 Å^3
• Polar Surface Area: 102.29 Å^2

DETAILS

Toronto Research Chemicals - H952175

3(S)-Hydroperoxy Simvastatin is the oxidative degradation product of Simvastatin (S485000).