A Comparative QSAR Study Using Wiener, Szeged, and Molecular Connectivity Indices

Mandloi, Manorama; Sikarwar, Arun; Sapre, Nitin S.; Karmarkar, Sneha; Khadikar, Padmakar V.

doi:10.1021/ci980139h

Cited by 31 publications

(17 citation statements)

References 17 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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“…Since the experimental determination of the partition coefficient of a large set of compounds is a very tedious job, several methods of calculations of log P o/w values have been proposed by different groups of authors, e.g., Rekker et al [7], Leo et al [8,9], Crippen et al [10,11], Bodor et al [12], Klopman and Wang [13], Moriguchi et al [14], and Suzuki and Kudo [15]. Many studies on the modeling of log P o/w values using topological, topographic, quantum chemical, and other descriptors have been reported where log P o/w values have been the response variable to explore suitability of the descriptors/schemes in QSPR studies [16][17][18][19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Quantitative structure–property relationship study of n-octanol–water partition coefficients of some of diverse drugs using multiple linear regression

Ghasemi

Saaidpour

2007

Analytica Chimica Acta

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“…Where V i and V j are the degrees of adjacent vertices i and j and n is the number of vertices in the hydrogen suppressed molecular structure [2,13,17]. The Eccentric Connectivity Index was introduced in 1997 by Sharma et al [9].…”

Section: Introductionmentioning

confidence: 99%

Model for Prediction of Anti‐HIV Activity of 2‐Pyridinone Derivatives Using Novel Topological Descriptor

et al. 2006

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A novel highly discriminating adjacency-cum-distance based topological descriptor, termed as augmented eccentric connectivity index, has been conceptualized and its discriminating power investigated with regard to anti-HIV activity of 2-pyridinone derivatives. The discriminating power of the augmented eccentric connectivity index was found to be far superior when compared to that of the distance based Wieners index and adjacency based molecular connectivity index. This index did not exhibit any degeneracy amongst all possible structures with three, four and five vertices. The values of augmented eccentric connectivity index, Wieners index and first-order molecular connectivity index of each of the 72 3-aminopyridin-2(1H)-one analogues comprising the dataset were computed using in-house computer program. The resulting data was analyzed and suitable models were developed after identification of the active ranges. Subsequently, a biological activity was assigned to each of the compounds involved in the dataset using these models which was then compared with the reported anti-HIV activity. High degree of prediction ranging from 81% to 89% was observed using models based upon these topological descriptors. Exceptionally high discriminating power amalgamated with decreased degeneracy of the proposed index, offers a vast potential for structure-activity/property studies.

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A Comparative QSAR Study Using Wiener, Szeged, and Molecular Connectivity Indices

Cited by 31 publications

References 17 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)

Quantitative structure–property relationship study of n-octanol–water partition coefficients of some of diverse drugs using multiple linear regression

Model for Prediction of Anti‐HIV Activity of 2‐Pyridinone Derivatives Using Novel Topological Descriptor

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