(1S,3S,7S,8S,8aR)-3-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(2H3)methylbutanoate

• ChemBase ID: 176865
• Molecular Formular: C23H34O6
• Molecular Mass: 406.51246
• Monoisotopic Mass: 406.23553881
• 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)O)OC(=O)[C@@H](CC)C
• Canonical SMILES: CC[C@H](C(=O)O[C@H]1C[C@H](O)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
• InChI: InChI=1S/C23H34O6/c1-4-13(2)23(27)29-20-11-16(24)9-15-6-5-14(3)19(22(15)20)8-7-18-10-17(25)12-21(26)28-18/h5-6,9,13-14,16-20,22,24-25H,4,7-8,10-12H2,1-3H3/t13-,14+,16-,17-,18-,19+,20+,22+/m1/s1
• InChIKey: OQARDMYXSOFTLN-IBVNNLIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,7S,8S,8aR)-3-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,3S,7S,8S,8aR)-3-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• Synonyms: (2S)-2-(Methyl-d3)butanoic Acid (1S,3S,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3-hydroxy-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; R 414-d3; Pravastatin Lactone-d3

Database IDs

• PubChem SID: 164232775
• PubChem CID: 71751738

CALCULATED PROPERTIES

• Acid pKa: 14.54432
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3115628
• LogD (pH = 7.4): 2.3115628
• Log P: 2.3115628
• Molar Refractivity: 110.1057 cm^3
• Polarizability: 43.21732 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P701192

A labelled metabolite of Pravastatin.

REFERENCES

• Boberg, M., et al.: Drug Metab. Dispos., 25, 321 (1997)
• Neuvonen, P., et al.: Clin. Pharmacol. Ther., 63, 332 (1997)
• Boyd, R., et al.: J. Clin. Pharmacol., 40, 91 (1997)