(3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid

• ChemBase ID: 167822
• Molecular Formular: C18H28O6
• Molecular Mass: 340.41132
• Monoisotopic Mass: 340.18858862
• 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)O
• 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)O)O
• InChI: InChI=1S/C18H28O6/c1-10-2-3-11-6-13(20)8-16(22)18(11)15(10)5-4-12(19)7-14(21)9-17(23)24/h2-3,6,10,12-16,18-22H,4-5,7-9H2,1H3,(H,23,24)/t10-,12+,13+,14+,15-,16-,18-/m0/s1
• InChIKey: ZDADMCPDUNEBIX-CGDZNSRRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• IUPAC Traditional name: (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6,8-dihydroxy-2-methyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
• Synonyms: [1S-[1α(βS*,δS*),2α,6α,8β,8aα]]- 1,2,6,7,8,8a-Hexahydro-β,δ,6,8-tetrahydroxy-2-methyl-1-naphthaleneheptanoic Acid; Des(2-methylbutyryl) Pravastatin

Database IDs

• CAS Number: 151006-03-0
• PubChem SID: 162261955
• PubChem CID: 22856170

CALCULATED PROPERTIES

• Acid pKa: 4.212299
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -1.7891773
• LogD (pH = 7.4): -3.5071752
• Log P: -0.48212457
• Molar Refractivity: 90.644 cm^3
• Polarizability: 34.99162 Å^3
• Polar Surface Area: 118.22 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D452870

Provastatin (P702000) impurity, a novel HMG-CoA reductase inhibitor.

REFERENCES

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