(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 (2S,3S)-3-hydroxy-2-methylbutanoate

• ChemBase ID: 170706
• Molecular Formular: C24H36O6
• Molecular Mass: 420.53904
• Monoisotopic Mass: 420.25118887
• 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]([C@@H](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@H]([C@@H](O)C)C)C)OC(=O)C1
• InChI: InChI=1S/C24H36O6/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/h5-6,9,13-16,18-21,23,25-26H,7-8,10-12H2,1-4H3/t13-,14-,15-,16-,18+,19+,20-,21-,23-/m0/s1
• InChIKey: PEIPDDGCLUETGA-DKAWXBQCSA-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 (2S,3S)-3-hydroxy-2-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 (2S,3S)-3-hydroxy-2-methylbutanoate
• Synonyms: [1S-[1α(2R*,3R*),3α,7β,8β(2S*,4S*),8aβ]]-3-Hydroxy-2-methylbutanoic Acid 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl Ester; (S,S)-3-Hydroxy Lovastatin

Database IDs

• CAS Number: 127910-58-1
• PubChem SID: 164226616
• PubChem CID: 71749093

CALCULATED PROPERTIES

• Acid pKa: 14.666318
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.5934222
• LogD (pH = 7.4): 2.5934222
• Log P: 2.5934222
• Molar Refractivity: 114.7749 cm^3
• Polarizability: 45.05363 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H943850

(S,S)-3-Hydroxy Lovastatin is a metabolite of Lovastatin (L472225).

REFERENCES

• Vyas, K.P., et al.: Drug Metab. Dispos., 18, 203 (1990)