The natural physiologically active compound gossvpol easily forms clathrate compounds with almost all low-molecular organic substances. The clathrates and the polymorphs of gossypol with known structures are classified into 24 groups of isostructural crystals. They differ from each other in the type of molecular association of gossypol. All possible types of gossypol association with predominant intermolecular H-bonds are analyzed in detail. Zero-, one- and two- dimensional associates are formed; each type of associate, except the zero-dimensional one, is built from more than one system of interm olecular H-bonds. An attempt is made to find out the reasons for the diversity of the types of gossypol supramolecular association based on the specific features of the molecular structure of gossypol.