In addition to be on par with non-chiral fingerprints for the above virtual screening benchmarks, one would expect a chiral fingerprint to distinguish all possible stereoisomers of a chiral molecule. To test the chiral differentiation of our fingerprints, we investigated their ability to assign a different fingerprint value for each stereoisomer on a series of stereochemically complex molecules comprizing carbohydrates, peptides and macrocyclic natural products containing up to thousands of stereoisomers per molecule (Figure and Table ).