Flavonoid alkaloids represent interesting subgroup of alkaloid family. Several plants containing flavonoid alkaloids are used in the folk medicine for the treatment of various diseases. Interesting biological properties of flavonoid alkaloids make them attractive candidates for lead compounds in drug discovery. Capitavine, or 5,7-dihydroxy-6-(1-methylpiperidin-2-yl)flavone and related compounds belong to piperidine-flavonoid alkaloids, possessing a piperidine ring connected to the C6-position of flavonoid skeleton, while buchenavianine is C8 piperidine-bonded analog. Capitavine derivatives were isolated mainly from Buchenavia capitata, buchevianine derivatives are present mainly in B. macrophylla. It was found, the chloroform extract of the leaves of B. capitata showed anti-HIV activity. The biological activity of capitavine and buchevianine derivatives needs to be investigated within the perspective of their pharmacokinetic properties and the toxicity, which are important factors in finding potential drug candidate. The present in silico study using SwissADME, Osiris and Molinspiration softwares showed, studied capitavine-derived flavonoid alkaloids exhibit considerable bioactivity for GPCR ligand (0.12 to 0.20), as enzyme inhibitor (0.17 to 0.22) and as nuclear receptor ligand (0.07 to 0.28). All compounds exhibit good gastrointestinal absorption and low risk of being irritants, tumorigenic or to have reproductive effect. The risk of mutagenicity was calculated for two compounds related to buchevianin and at this point the role of 5-methoxy group appears to be crucial for the low risk of mutagenicity.