(1S,3R,7S,8S,8aR)-3,7-dimethyl-8-{2-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate

• ChemBase ID: 165648
• Molecular Formular: C24H34O4
• Molecular Mass: 386.52436
• Monoisotopic Mass: 386.24570957
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C=CC1)C)OC(=O)[C@H](CC)C
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1CC=CC(=O)O1)[C@H](C=C2)C)C
• InChI: InChI=1S/C24H34O4/c1-5-16(3)24(26)28-21-14-15(2)13-18-10-9-17(4)20(23(18)21)12-11-19-7-6-8-22(25)27-19/h6,8-10,13,15-17,19-21,23H,5,7,11-12,14H2,1-4H3/t15-,16-,17-,19-,20-,21-,23-/m0/s1
• InChIKey: SPIVMHAGTHFLMO-OCAGQIGWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-{2-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl}-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-{2-[(2R)-6-oxo-2,3-dihydropyran-2-yl]ethyl}-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
• Synonyms: (2S)-2-Methylbutanoic Acid (1S,3R,7S,8S,8aR)-8-[2-[(2R)-3,6-Dihydro-6-oxo-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl Ester; Dehydromonacolin K; L 642257; α,β-Dehydrolovastatin; Dehydro Lovastatin

Database IDs

• CAS Number: 109273-98-5
• PubChem SID: 162259781
• PubChem CID: 71315317

CALCULATED PROPERTIES

• Acid pKa: 17.274105
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.436949
• LogD (pH = 7.4): 5.436949
• Log P: 5.436949
• Molar Refractivity: 112.8038 cm^3
• Polarizability: 43.549904 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229685

Lovastatin impurity.

REFERENCES

• Duggan, D., et al.: Drug Metab. Dispos., 17, 166 (1989)
• Wang-Iverson, D., et al.: Drugs, 23, 127 (1989)
• Wu, Y., et al.: J. Pharm. Biomed. Anal., 20, 471 (1989)