sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-8-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]oxy}-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 171145
• Molecular Formular: C23H35NaO8
• Molecular Mass: 462.50897
• Monoisotopic Mass: 462.22296236
• SMILES: [C@@H]1(C[C@@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)O)OC(=O)[C@H]([C@@H](O)C)C.[Na+]
• Canonical SMILES: O[C@@H](C[C@H](CC(=O)[O-])O)CC[C@H]1[C@@H](C)C=CC2=C[C@H](C[C@@H]([C@H]12)OC(=O)[C@H]([C@@H](O)C)C)O.[Na+]
• InChI: InChI=1S/C23H36O8.Na/c1-12-4-5-15-8-17(26)10-20(31-23(30)13(2)14(3)24)22(15)19(12)7-6-16(25)9-18(27)11-21(28)29;/h4-5,8,12-14,16-20,22,24-27H,6-7,9-11H2,1-3H3,(H,28,29);/q;+1/p-1/t12-,13-,14-,16+,17+,18+,19-,20-,22-;/m0./s1
• InChIKey: AIKHPBQZWYYTKO-FVDQBCLRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-8-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]oxy}-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-8-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]oxy}-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR,δR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ,6-trihydroxy-8-[(2S,3S)-3-hydroxy-2-methyl-1-oxobutoxy]-2-methyl-1-naphthaleneheptanoic Acid Sodium; (3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-8-[[(2S,3S)-3-hydroxy-2-methylbutanoyl]oxy]2-methyl1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic Acid Sodium; (S)-3''-Hydroxy Pravastatin Sodium Salt

Database IDs

• CAS Number: 722504-45-2
• PubChem SID: 164227055
• PubChem CID: 58746967

CALCULATED PROPERTIES

• Acid pKa: 4.212299
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.96872586
• LogD (pH = 7.4): -2.6867237
• Log P: 0.3383268
• Molar Refractivity: 126.0275 cm^3
• Polarizability: 44.882004 Å^3
• Polar Surface Area: 147.35 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952290

The (S)-3’’-hydroxylated metabolite of Pravastatin in humans.

REFERENCES

• Everett, D. W., et al.: Drug Metab. Dispos., 19, 740 (1991)