(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 2-methyl-3-oxobutanoate

• ChemBase ID: 172084
• Molecular Formular: C24H34O6
• Molecular Mass: 418.52316
• Monoisotopic Mass: 418.23553881
• 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)C)OC(=O)C(C(=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(C(=O)C)C)C)OC(=O)C1
• InChI: InChI=1S/C24H34O6/c1-13-9-17-6-5-14(2)20(8-7-19-11-18(26)12-22(27)29-19)23(17)21(10-13)30-24(28)15(3)16(4)25/h5-6,9,13-15,18-21,23,26H,7-8,10-12H2,1-4H3/t13-,14-,15?,18+,19+,20-,21-,23-/m0/s1
• InChIKey: NXZRZXCVBJAQDF-KZDKVUJMSA-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 2-methyl-3-oxobutanoate
• 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 2-methyl-3-oxobutanoate
• Synonyms: (4R,6R)-6-[2-(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-Hexahydro-2,6-dimethyl-8-(2-methyl-1,3-dioxobutoxy)-1-napthyl]ethyl]tetrahydro-4-hydroxy-2H-pyran-2-one; (4R,6R)-6-[2-(1S,2S,6R,8S,8aR)-Monacolin X; Keto Lovastatin

Database IDs

• PubChem SID: 164227994
• PubChem CID: 71749687

CALCULATED PROPERTIES

• Acid pKa: 10.581652
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.2122662
• LogD (pH = 7.4): 3.2119863
• Log P: 2.9789364
• Molar Refractivity: 113.8497 cm^3
• Polarizability: 44.51012 Å^3
• Polar Surface Area: 89.9 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K195400

Keto Lovastatin is an impurity of Lovastatin (L472225).

REFERENCES

• Endo, A., et al.: J. Antibiot., 33, 334 (1980)
• Endo, A., et al.: J. Med. Chem., 28, 401 (1980)