Fig. 1

Examples illustrating the characteristics of property and fingerprint descriptors. For fingerprint, ECFP4 was calculated using the Pipeline Pilot software [22]; the numbers are shown as their own specific substructures. For properties, ClogP and pKa were calculated using the Daylight software [23] and the ChemAxon pKa plugin [24], respectively. a The fingerprint can distinguish between the relative positions of fluorine and chlorine atoms, but the property cannot. b The fingerprint shows that the difference between ethane and acetic acid is equal to that between ethane and methanesulfonate. By contrast, the property shows the difference between the acidic strengths of the two molecules