The molecular structure of (20R)-20-phenyl-5-pregnene-3 beta, 20-diol, an inhibitor of cholesterol conversion to pregnenolone.
The crystal and molecular structure of (20R)-20-phenyl-5-pregnene-3 beta, 20-diol hemihydrate has been determined by X-ray analysis in order to establish the configuration and conformation at C(20). Interest in this compound was stimulated by its high affinity inhibitory binding to cytochrome P-450SCC, the enzyme which catalyzes the biosynthesis of pregnenolone (3 beta-hydroxy-5-pregnen-20-one) from cholesterol. The results of the analysis suggest a possible conformation for the cholesterol side chain in the enzyme complex.
D002784:Cholesterol / Q000378:metabolism*; D065607:Cytochrome P-450 Enzyme Inhibitors; D008958:Models, Molecular; D011283:Pregnenes / Q000494:pharmacology*; D011284:Pregnenolone / Q000378:metabolism*; D014961:X-Ray Diffraction
C012486:20-phenyl-5-pregnene-3 beta,20-diol; D065607:Cytochrome P-450 Enzyme Inhibitors; D011283:Pregnenes; D011284:Pregnenolone; D002784:Cholesterol