(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 (2S,3S)-3-hydroxy-2-methylbutanoate

• ChemBase ID: 171146
• Molecular Formular: C23H34O7
• Molecular Mass: 422.51186
• Monoisotopic Mass: 422.23045343
• 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]([C@@H](O)C)C
• Canonical SMILES: O[C@@H]1C[C@@H](CC[C@H]2[C@@H](C)C=CC3=C[C@H](C[C@@H]([C@H]23)OC(=O)[C@H]([C@@H](O)C)C)O)OC(=O)C1
• InChI: InChI=1S/C23H34O7/c1-12-4-5-15-8-16(25)10-20(30-23(28)13(2)14(3)24)22(15)19(12)7-6-18-9-17(26)11-21(27)29-18/h4-5,8,12-14,16-20,22,24-26H,6-7,9-11H2,1-3H3/t12-,13-,14-,16+,17+,18+,19-,20-,22-/m0/s1
• InChIKey: JFMJNFGZWOISEH-FBIVGABFSA-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 (2S,3S)-3-hydroxy-2-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 (2S,3S)-3-hydroxy-2-methylbutanoate
• Synonyms: (2S,3’’S)-3’’-Hydroxy-2-methylbutanoic 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; (S)-3''-Hydroxy Pravastatin Lactone

Database IDs

• PubChem SID: 164227056
• PubChem CID: 71749278

CALCULATED PROPERTIES

• Acid pKa: 14.420883
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.002798
• LogD (pH = 7.4): 1.002798
• Log P: 1.002798
• Molar Refractivity: 111.6982 cm^3
• Polarizability: 43.86667 Å^3
• Polar Surface Area: 113.29 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952293

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