QSPR modeling of enthalpies of formation for organometallic compounds by SMART‐based optimal descriptors

A quantitative structure‐property relationship (QSPR) model for the prediction of gas‐phase enthalpy of formation has been developed, using as chemical information descriptors based on the SMART notation, which is an alternative to SMILES. The model is one‐variable equation. The SMART‐based descriptors are calculated with correlation weights of SMART attributes which are obtained by the Monte Carlo method. The model addressed organometallic compounds. Statistical characteristics of the model are the following: n = 104, r2 = 0.9944, s = 19.6 (kJ/mol), F = 18,269 (training set) and n = 28, r2 = 0.9909, s = 28.8 (kJ/mol), F = 2832 (test set). © 2009 Wiley Periodicals, Inc. J Comput Chem, 2009

[1]  J. M. Simoes,et al.  Estimation of enthalpies of formation of organometallic compounds from their molecular structures , 2008 .

[2]  Jerzy Leszczynski,et al.  Multiplicative SMILES-based optimal descriptors: QSPR modeling of fullerene C60 solubility in organic solvents , 2007 .

[3]  Haralambos Sarimveis,et al.  Prediction of intrinsic viscosity in polymer-solvent combinations using a QSPR model , 2006 .

[4]  Francisco Torrens,et al.  Atom-based non-stochastic and stochastic bilinear indices: Application to QSPR/QSAR studies of organic compounds , 2008 .

[5]  E. Benfenati,et al.  Optimisation of correlation weights of SMILES invariants for modelling oral quail toxicity. , 2007, European journal of medicinal chemistry.

[6]  I. Gutman,et al.  Comparison of QSPR Models Based on Hydrogen-Filled Graphs and on Graphs of Atomic Orbitals , 2005 .

[7]  P. Roy,et al.  On Some Aspects of Variable Selection for Partial Least Squares Regression Models , 2008 .

[8]  Emilio Benfenati,et al.  QSPR modeling for enthalpies of formation of organometallic compounds by means of SMILES-based optimal descriptors , 2008 .

[9]  Emilio Benfenati,et al.  SMILES in QSPR/QSAR Modeling: results and perspectives. , 2007, Current drug discovery technologies.

[10]  Jerzy Leszczynski,et al.  QSAR modeling of acute toxicity by balance of correlations. , 2008, Bioorganic & medicinal chemistry.

[11]  Kunal Roy,et al.  QSTR with Extended Topochemical Atom Indices. 10. Modeling of Toxicity of Organic Chemicals to Humans Using Different Chemometric Tools , 2008, Chemical biology & drug design.

[12]  Alan Talevi,et al.  New QSPR study for the prediction of aqueous solubility of drug-like compounds. , 2008, Bioorganic & medicinal chemistry.

[13]  Kunal Roy,et al.  QSAR modeling for lipid peroxidation inhibition potential of flavonoids using topological and structural parameters , 2008 .

[14]  Eduardo A. Castro,et al.  Partial Order Ranking for the aqueous toxicity of aromatic mixtures , 2008 .

[15]  A. Tropsha,et al.  Beware of q2! , 2002, Journal of molecular graphics & modelling.

[16]  David Weininger,et al.  SMILES. 2. Algorithm for generation of unique SMILES notation , 1989, J. Chem. Inf. Comput. Sci..

[17]  David Weininger,et al.  SMILES, a chemical language and information system. 1. Introduction to methodology and encoding rules , 1988, J. Chem. Inf. Comput. Sci..

[18]  David Vidal,et al.  LINGO, an Efficient Holographic Text Based Method To Calculate Biophysical Properties and Intermolecular Similarities , 2005, J. Chem. Inf. Model..

[19]  David Weininger,et al.  SMILES, 3. DEPICT. Graphical depiction of chemical structures , 1990, J. Chem. Inf. Comput. Sci..

[20]  Tomasz Puzyn,et al.  QSPR-based estimation of the atmospheric persistence for chloronaphthalene congeners , 2008 .

[21]  K. B. Yatsimirskii,et al.  Thermodynamic Parameters of the Formation of 3d Transition Metal Complexes as Model Systems for Description of Substrate-Receptor Interaction , 2005 .

[22]  Jerzy Leszczynski,et al.  Multiple Linear Regression Analysis and Optimal Descriptors: Predicting the Cholesteryl Ester Transfer Protein Inhibition Activity , 2008 .

[23]  Haralambos Sarimveis,et al.  A Novel QSAR Model for Evaluating and Predicting the Inhibition Activity of Dipeptidyl Aspartyl Fluoromethylketones , 2006 .