(2R,4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-2,3,4,4a,5,6-hexahydronaphthalene-2-carboxylic acid

• ChemBase ID: 163789
• Molecular Formular: C25H36O7
• Molecular Mass: 448.54914
• Monoisotopic Mass: 448.24610349
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)O)C(=O)O)OC(=O)C(C)(C)CC
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C(=O)O)(C)C
• InChI: InChI=1S/C25H36O7/c1-5-25(3,4)24(30)32-20-11-16(23(28)29)10-15-7-6-14(2)19(22(15)20)9-8-18-12-17(26)13-21(27)31-18/h6-7,10,14,16-20,22,26H,5,8-9,11-13H2,1-4H3,(H,28,29)/t14-,16-,17+,18+,19-,20-,22-/m0/s1
• InChIKey: XKRMLBJLSDIWTC-AEEZTXMNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-2,3,4,4a,5,6-hexahydronaphthalene-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,4aR,5S,6S)-4-[(2,2-dimethylbutanoyl)oxy]-5-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-6-methyl-2,3,4,4a,5,6-hexahydronaphthalene-2-carboxylic acid
• Synonyms: [2R-[2α,4α,4aβ,5β(2R*,4R*),6β]]-4-(2,2-Dimethyl-1-oxobutoxy)-2,3,4,4a,5,6-hexahydro-6-methyl-5-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-2-naphthalenecarboxylic Acid; 6'-Carboxy Simvastatin

Database IDs

• CAS Number: 114883-30-6
• PubChem SID: 162257924
• PubChem CID: 14373154

CALCULATED PROPERTIES

• Acid pKa: 4.434917
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.2944689
• LogD (pH = 7.4): 0.53308445
• Log P: 3.3939266
• Molar Refractivity: 119.3747 cm^3
• Polarizability: 46.816006 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; methanol
• Apperance: Off-White Solid
• Melting Point: 175-179°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C182400

A HMG-COA reductase inhibitor; useful as anticholesteramic.