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

• ChemBase ID: 167539
• Molecular Formular: C24H38O5
• Molecular Mass: 406.55552
• Monoisotopic Mass: 406.27192432
• SMILES: [C@@H]1(C[C@H](C[C@H]2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@@H](C1)O)C)OC(=O)[C@H](CC)C
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C[C@H]2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
• InChI: InChI=1S/C24H38O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,14-21,23,25H,5,8-13H2,1-4H3/t14-,15-,16-,17-,18+,19+,20-,21-,23-/m0/s1
• InChIKey: IFIFFBWHLKGTMO-SJIDJMGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate
• IUPAC Traditional name: (1S,3S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl (2S)-2-methylbutanoate
• Synonyms: (2S)-2-Methylbutanoic Acid (1S,3S,4aR,7S,8S,8aS)-1,2,3,4,4a,7,8,8a-Octahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; (+)-Dihydromevinolin; Dihydrolovastatin; Dihydromevinolin; L 154883; MSD 883; 4a,5-Dihydro Lovastatin

Database IDs

• CAS Number: 77517-29-4
• PubChem SID: 162261672
• PubChem CID: 11080021

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.3077664
• LogD (pH = 7.4): 4.3077664
• Log P: 4.3077664
• Molar Refractivity: 112.3324 cm^3
• Polarizability: 44.660286 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D448570

4a,5-Dihydro Lovastatin is an impurity in Lovastatin (L472225) bulk drug.

REFERENCES

• Bone, E.A., et al.: Bioorg. Med. Chem. Lett., 2, 223 (1992)
• Houck, A., et al.: Talanta, 40, 491 (1992)