Definition of pharmacophore structures for individual off-target receptor sites.

<p>(A) Colors code the degree of tolerance of appended groups: pharmacophores (minimum structural requirement for binding, shown on <b>1</b> as template) are shown in black, favorable or tolerated substituents are shown in green and not tolerated substituents are shown in red. Some residues predicted to be in contact with the adenosine derivatives at the off-target receptors are highlighted according to the explanations provided in the text (corresponding to poses shown in <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0097858#pone-0097858-g004" target="_blank">Figure 4B</a> for the h5HT₂ receptors and <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0097858#pone-0097858-g007" target="_blank">Figure 7B</a> for the hβ₃ receptor. This is an approximation based on a limited set of compounds. Pharmacophores for other targets were not well defined with the current data set, and weak hits correspond to individual compounds as noted in <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0097858#pone-0097858-t001" target="_blank">Table 1</a>. (B) A comparison with the residues in contact with compound <b>1</b> at the A₃AR, as previously predicted by docking studies <a href="http://www.plosone.org/article/info:doi/10.1371/journal.pone.0097858#pone.0097858-Tosh1" target="_blank">[16]</a>.