3D Connectivity Indices in QSPR/QSAR Studies

Estrada, Ernesto; Molina, Enrique

doi:10.1021/ci000156i

Cited by 67 publications

(69 citation statements)

References 45 publications

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“…[6][7][8][9] Many studies on the modeling of log K o/w values using topological, topographic, quantum chemical and other descriptors have been reported where log K o/w values have been the response variable to explore suitability of the descriptors/schemes in QSPR studies. [10][11][12][13][14][15][16] There are some reports about the applications of MLR [17][18][19][20] and artificial neural network, [21][22][23][24] modeling to predict the n-octanol/water partition coefficient of organic compounds. Some of papers, about application of QSPR techniques in the development of a new and simplified approach to prediction of compounds properties were published.…”

Section: Introductionmentioning

confidence: 99%

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Goudarzi¹,

Goodarzi²

2010

J. Braz. Chem. Soc.

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Neste trabalho, nós introduzimos um novo método da função de base radial por regressão de mínimos quadrados (RBF-PLS) com elevada exatidão e precisão nos estudos quantitativos da relação entre a estrutura-propriedade de compostos orgânicos (QSPR). Três métodos QSPR foram comparados para a predição dos coeficientes de partição no sistema n-octanol-água (K o/w ) (de alguns compostos orgânicos). A regressão linear múltipla (MLR), a regressão parcial dos mínimos quadrados (PLS) e a regressão base radial com funções pelo método de mínimos quadrados (RBF-PLS) foram empregadas para construir os modelos lineares e não-lineares e predizer o valor de K o/w . Os descritores teóricos foram calculados por Dragon e por Gaussian 98 e foram explorados pelas regressões parciais, codificando diferentes aspectos topológicos, geométricos e eletrônicos das estruturas moleculares. A raiz quadrada dos erros médios previstos (RMSEP) para as etapas de testes e da previsão teórica por modelos de MLR, de PLS e de RBF-PLS foram 0,4022; 0,4128; 0,3050; 0,3564; 0,0364 e 0,0533 respectivamente. Também, o erro padrão relativo previsto (RSEP) para os testes e de previsão teórica por MLR, PLS e RBF-PLS foram de 13,24; 13,60; 10,04; 11,74; 1,197 e 1,757 respectivamente. Os dados mostram que o RBF-PLS produziu resultados melhores do que PLS e MLR.In this work, we introduce a new method ability radial basic function-partial least square (RBF-PLS) with high accuracy and precision in QSPR studies. Three quantitative structure-propertty relationship (QSPR) methods have been compared for the prediction of n-octanol-water partition coefficients (K o/w ) of some organic compounds. The multiple linear regressions (MLR), partial least square (PLS) and radial basis function-partial least squares (RBF-PLS) models were employed to construct linear and nonlinear models to predict of K o/w . The theoretical descriptors that calculated by Dragon and Gaussian 98 were explored by stepwise regressions, encoding different aspects of the topological, geometrical and electronic molecular structures. The root means square error of prediction (RMSEP) for training and prediction sets by MLR, PLS and RBF-PLS models were 0.4022, 0.4128, 0.3050, 0.3564, 0.0364 and 0.0533, respectively. Also, the relative standard error of prediction (RSEP) for training and prediction sets by MLR, PLS and RBF-PLS models were 13. 24, 13.60, 10.04, 11.74, 1.197 and 1.757 respectively. The resultant data explained that RBF-PLS produced better results than PLS and MLR.

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Section: Introductionmentioning

confidence: 99%

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Goudarzi¹,

Goodarzi²

2010

J. Braz. Chem. Soc.

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“…These chemicals have different substituents at position 5 of the furan ring as well as at the β position of the exocyclic double bond [38,39]. The structures of these 34 furylethylene derivatives are given in Table 3.…”

Section: Data Set For Qspr/qsar Studiesmentioning

confidence: 99%

“…The antibacterial activity of these compounds was determined as the inverse of the concentration C that produces 50% of growth inhibition in E. coli at six different times and reported as log (1/C) [38]. This antibacterial activity was used to classify furylethylenes in two groups by Estrada and Molina [39]. The group of active compounds is composed of those compounds having values of log (1/C) < 3, while the rest formed group of inactive compounds.…”

Section: Data Set For Qspr/qsar Studiesmentioning

confidence: 99%

“…Table 6 illustrates the classification of 2-furylethylene derivatives as antibacterial according to this experimental cutoff value. This Table also depicts the antibacterial activity of a series of nine new 2-furylethylenes using by Estrada and Molina [39] like external prediction (test) set. These compounds have a NO 2 group at position R 3 and a Br or I at positions R 1 and/or R 2 .…”

Section: Data Set For Qspr/qsar Studiesmentioning

confidence: 99%

“…The partition coefficient n-octanol/water (log P) has an important role in the understanding of the biological behavior of these 2-furylethylene derivatives [38]. Consequently, we will study this parameter to compare the possibilities of molecular linear indices in QSPR and to compare this result to those obtained by Estrada and Molina [39] using 2D and 3D (topographic) connectivity indices (vertex and edge ones), and quantum chemical descriptors.…”

Section: Modeling Partition Coefficients (Log P) Of 34 2-furylethylenmentioning

confidence: 99%

See 2 more Smart Citations

Atom, Atom-Type, and Total Linear Indices of the “Molecular Pseudograph’s Atom Adjacency Matrix”: Application to QSPR/QSAR Studies of Organic Compounds

et al. 2004

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Abstract:In this paper we describe the application in QSPR/QSAR studies of a new group of molecular descriptors: atom, atom-type and total linear indices of the molecular pseudograph's atom adjacency matrix. These novel molecular descriptors were used for the prediction of boiling point and partition coefficient (log P), specific rate constant (log k), and antibacterial activity of 28 alkyl-alcohols and 34 derivatives of 2-furylethylenes, respectively. For this purpose two quantitative models were obtained to describe the alkyl-alcohols' boiling points. The first one includes only two total linear indices and showed a good behavior from a statistical point of view (R 2 = 0.984, s = 3.78, F = 748.57, linear discriminant model for classifying antibacterial activity of these compounds was also achieved with the use of the atom and atom-type linear indices. The global percent of good classification in training and external test set obtained was of 94.12% and 100.0%, respectively. The comparison with other approaches (connectivity indices, total and local spectral moments, quantum chemical descriptors, topographic indices and Estate/biomolecular encounter parameters) reveals a good behavior of our method. The approach described in this paper appears to be a very promising structural invariant, useful for QSPR/QSAR studies and computer-aided "rational" drug design.

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2009

Molecular Descriptors for Chemoinformatics

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3D Connectivity Indices in QSPR/QSAR Studies

Cited by 67 publications

References 45 publications

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

QSPR study of partition coefficient (Ko/w) of some organic compounds using radial basic function-partial least square (RBF-PLS)

Atom, Atom-Type, and Total Linear Indices of the “Molecular Pseudograph’s Atom Adjacency Matrix”: Application to QSPR/QSAR Studies of Organic Compounds

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