Abstract
A set of eighteen neolignan derivative compounds with anti-schistosomiasis activity was studied by using the quantum mechanical semi-empirical method PM3 and other theoretical methods in order to calculate selected molecular properties (variables or descriptors) to be correlated to their biological activities. Exploratory data analysis (principal component analysis, PCA, and hierarchical cluster analysis, HCA), discriminant analysis (DA) and the Kth nearest neighbor (KNN) method were employed for obtaining possible relationships between the calculated descriptors and the biological activities studied and predicting the anti-schistosomiasis activity of new compounds from a test set. The molecular descriptors responsible for the separation between active and inactive compounds were: hydration energy (HE), molecular refractivity (MR) and charge on the C19 carbon atom (Q19). These descriptors give information on the kind of interaction that can occur between the compounds and their respective biological receptor. The prediction study was done with a new set of ten derivative compounds by using the PCA, HCA, DA and KNN methods and only five of them were predicted as active against schistosomiasis.
Highlights
Neolignans are dimers obtained from oxidative coupling of allyl and propenyl phenols occurring in the Myristicaceae and other primitive plant families
The calculated descriptors were selected so that they could represent electronic (HOMO, LUMO, χ, POL, Q2, Q3, Q12, Q13, Q19, molecular refractivity (MR) and hydration energy (HE)), steric (t, d and VOL) and hydrophobic (Log P) properties of the compounds studied. These properties are supposed to be important to explain the anti-schistosomiasis activity of the neolignan molecules under study here[9] and the number of calculated descriptors was limited by the softwares we used in the calculations
The central idea of Principal component analysis (PCA) is to reduce the dimensionality of the data set explaining the variance-covariance structure
Summary
The calculated descriptors were selected so that they could represent electronic (HOMO, LUMO, χ, POL, Q2, Q3, Q12, Q13, Q19, MR and HE), steric (t, d and VOL) and hydrophobic (Log P) properties of the compounds studied. These properties (descriptors) are supposed to be important to explain the anti-schistosomiasis activity of the neolignan molecules under study here[9] and the number of calculated descriptors was limited by the softwares we used in the calculations. The charges derived from the electrostatic potential method are physically more satisfactory than the Mulliken’s charges,[17] especially when related to biological activity
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