(1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(2H3)methylbutanoate

• ChemBase ID: 172417
• Molecular Formular: C24H36O5
• Molecular Mass: 404.53964
• Monoisotopic Mass: 404.25627425
• 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[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=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
• InChI: InChI=1S/C24H36O5/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/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14-,15+,16-,18+,19+,20-,21-,23-/m0/s1
• InChIKey: PCZOHLXUXFIOCF-YPQFMRJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• Synonyms: (2S)-2-(Methyl-d3)butanoic Acid (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl Ester; MK-803-d3; Lovalip-d3; Lovastatin Lactone-d3; Mevacor-d3; Mevinacor-d3; Lovastatin-d3

Database IDs

• PubChem SID: 164228327
• PubChem CID: 71749847

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.9021869
• LogD (pH = 7.4): 3.9021869
• Log P: 3.9021869
• Molar Refractivity: 113.1824 cm^3
• Polarizability: 44.4169 Å^3
• Polar Surface Area: 72.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 152-155°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L472227

Labelled Lovastatin an antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase.

REFERENCES

• Bilheimer, D.W., et al.: Proc. Nat. Acad. Sci. USA, 80, 4124 (1983)