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

• ChemBase ID: 171149
• Molecular Formular: C23H34O6
• Molecular Mass: 406.51246
• Monoisotopic Mass: 406.23553881
• SMILES: [C@@H]1(CC=CC2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@@H]1C[C@H](CC(=O)O1)O)C)O)OC(=O)[C@@H](CC)C
• Canonical SMILES: CC[C@H](C(=O)O[C@H]1CC=CC2=C[C@H]([C@@H]([C@@H]([C@@H]12)CC[C@@H]1C[C@@H](O)CC(=O)O1)C)O)C
• InChI: InChI=1S/C23H34O6/c1-4-13(2)23(27)29-20-7-5-6-15-10-19(25)14(3)18(22(15)20)9-8-17-11-16(24)12-21(26)28-17/h5-6,10,13-14,16-20,22,24-25H,4,7-9,11-12H2,1-3H3/t13-,14-,16-,17-,18+,19-,20+,22+/m1/s1
• InChIKey: JCXABYACWXHFQQ-PQXOSVOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,6S,7R,8S,8aR)-6-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,6S,7R,8S,8aR)-6-hydroxy-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• Synonyms: 3α-iso-Pravastatin-d3; (2S)-2-(Methyl-d3)butanoic Acid (1S,6S,7R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-hydroxy-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; SQ 31906 Lactone-d3; 3α-Hydroxy Pravastatin Lactone-d3

Database IDs

• PubChem SID: 164227059
• PubChem CID: 71749280

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.4623103
• LogD (pH = 7.4): 2.4623106
• Log P: 2.4623106
• Molar Refractivity: 110.0723 cm^3
• Polarizability: 43.21732 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952302

A labelled metabolite of Pravastatin (P702000), a competitive inhibitor of HMG-CoA reductase.

REFERENCES

• Serizawa, N., et al.: J. Antibiot., 36, 604 (1983)
• White, H.D, et al.: N. Engl. J. Med., 343, 317 (2000)