(A) The reference compound 3-(2-oct-1-ynylphenyl) propanoic acid (OPPA) in complex with 1LOX; (B,D) Docking of OPPA to 1LOX (target box 35). The orientation of the compound is analogue to the original complex (In B. blue: polar interactions, brown: hydrophobic interactions, yellow: pi interactions). In the complex of 1LOX with OPPA (box 35), the carboxylic group of the ligand participates in polar interactions with Gln548 and His545. Hydrophobic interactions with His361, His366, Leu362 Ala404, Leu408 and Phe415 are observed while pi-pi interactions between Phe353 and carbon atoms of the phenyl ring of the ligand also take place; (C) Docking of OPPA to 1LOX (target box 30). The compound occupies an opposite orientation to than in the original complex.