(4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one

• ChemBase ID: 170492
• Molecular Formular: C19H28O4
• Molecular Mass: 320.42322
• Monoisotopic Mass: 320.19875938
• SMILES: C1[C@H](C=C2[C@H]([C@H]1O)[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)O)C
• Canonical SMILES: C[C@@H]1C[C@H](O)[C@H]2C(=C1)C=C[C@@H]([C@@H]2CC[C@@H]1C[C@@H](O)CC(=O)O1)C
• InChI: InChI=1S/C19H28O4/c1-11-7-13-4-3-12(2)16(19(13)17(21)8-11)6-5-15-9-14(20)10-18(22)23-15/h3-4,7,11-12,14-17,19-21H,5-6,8-10H2,1-2H3/t11-,12-,14+,15+,16-,17-,19-/m0/s1
• InChIKey: ZDFOBOYQVYMVCW-IRUSZSJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one
• IUPAC Traditional name: (4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-hydroxyoxan-2-one
• Synonyms: (4R,6R)-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one; Lovastatin Diol Lactone; Antibiotic MB 530A; Monacolin J; 6(R)-[2-(8(S)-Hydroxy]-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl]ethyl-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Database IDs

• CAS Number: 79952-42-4
• PubChem SID: 164226402
• PubChem CID: 9905162

CALCULATED PROPERTIES

• Acid pKa: 14.914537
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7729704
• LogD (pH = 7.4): 1.7729707
• Log P: 1.7729707
• Molar Refractivity: 90.2285 cm^3
• Polarizability: 35.062412 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMF; DMSO; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 109-114°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H941625

A Simvastatin intermediate; Lovastatin analog has the activities of decreasing blood cholesterol and low-d. lipoprotein, can be used to preparation hypolipidemic medicine.

REFERENCES

• Endo, A., et al.: J. Antibiot., 39, 1609 (1986)
• Aniya, Y., et al.: Gen. Pharmacol., 32, 225 (1986)
• Li, Y., et al.: J. Pharm. Biomed. Anal., 35, 1101 (1986)
• Akihisa, T., et al.: Chem. Biodivers, 2, 1305 (1986)