Many computational tasks related to small molecule drug discovery, such as similarity searches, target prediction, ligand-based virtual screening and visualization of large databases of drug-like molecules, can be performed using vectors encoding molecular structure, called molecular fingerprints. Remarkably, molecular fingerprints work quite well to classify and compare bioactive molecules without considering stereochemical information, which is somewhat surprising considering that biological matter is essentially chiral and stereo-defined at the molecular level, but also reflects the fact one only rarely needs to distinguish between different stereoisomers of small molecule drugs, in part simply because many drug-like compounds are achiral.