Stereo Signature Molecular Descriptor

We
present an algorithm to compute molecular graph descriptors
considering the stereochemistry of the molecular structure based on
our previously introduced signature molecular descriptor. The algorithm
can generate two types of descriptors, one which is compliant with
the Cahn–Ingold–Prelog priority rules, including complex
stereochemistry structures such as fullerenes, and a computationally
efficient one based on our previous definition of a directed acyclic
graph that is augmented to a chiral molecular graph. The performance
of the algorithm in terms of speed as a canonicalizer as well as in
modeling and predicting bioactivity is evaluated, showing an overall
better performance than other molecular descriptors, which is particularly
relevant in modeling stereoselective biochemical reactions. The complete
source code of the stereo signature molecular descriptor is available
for download under an open-source license at http://molsig.sourceforge.net.