sodium (3R,5R)-7-[(1S,2R,3S,5S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-3,5-dihydroxy-2,6-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 167802
• Molecular Formular: C25H41NaO8
• Molecular Mass: 492.57801
• Monoisotopic Mass: 492.26991255
• SMILES: [C@@H]1(C[C@H]([C@@H](C2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@H](C[C@H](CC(=O)[O-])O)O)C)O)O)C)OC(=O)C(CC)(C)C.[Na+]
• Canonical SMILES: CCC(C(=O)O[C@H]1C[C@@H](C)[C@@H](C2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@H](C[C@H](CC(=O)[O-])O)O)C)O)O)(C)C.[Na+]
• InChI: InChI=1S/C25H42O8.Na/c1-6-25(4,5)24(32)33-20-9-13(2)23(31)18-12-19(28)14(3)17(22(18)20)8-7-15(26)10-16(27)11-21(29)30;/h12-17,19-20,22-23,26-28,31H,6-11H2,1-5H3,(H,29,30);/q;+1/p-1/t13-,14-,15-,16-,17+,19-,20+,22-,23+;/m1./s1
• InChIKey: CTCJXNCXQFTEHG-VELUIITOSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[(1S,2R,3S,5S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-3,5-dihydroxy-2,6-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[(1S,2R,3S,5S,6R,8S,8aR)-8-[(2,2-dimethylbutanoyl)oxy]-3,5-dihydroxy-2,6-dimethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR,1S,2R,6R,8S,8aR)-8-(2,2-Dimethyl-1-oxobutoxy)-1,2,3,5,6,7,8,8a-octahydro-β,δ,3,5-tetrahydroxy-2,6-dimethyl-1-naphthaleneheptanoic Acid Sodium Salt; 3',5'-Dihydrodiol Simvastatin Acid Sodium Salt

Database IDs

• PubChem SID: 162261935
• PubChem CID: 71316236

CALCULATED PROPERTIES

• Acid pKa: 4.169862
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.50268793
• LogD (pH = 7.4): -1.203798
• Log P: 1.8499371
• Molar Refractivity: 133.7731 cm^3
• Polarizability: 48.792408 Å^3
• Polar Surface Area: 147.35 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452695

A metabolite of Simvastatin (S485000).

REFERENCES

• Pietro, D., et al.: Cardiovasc. Drug Rev., 8, 220 (1990)
• Prueksaritanont, T., et al.: Drug Metab. Dispos., 29, 1251 (1990)