Construction of High-Quality Structure−Property−Activity Regressions:  The Boiling Points of Sulfides

Randić, Milan; Basak, Subhash C.

doi:10.1021/ci990115q

Cited by 35 publications

(29 citation statements)

References 40 publications

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“…Recently, in addition to the use of variable connectivity indices [35][36][37][38][39][40][41][42][43], several different flexible molecular descriptors have been considered in the literature, including the use of variable paths weights [44,45], variable distance related indices [46,47], and other variable descriptors [48]. Thus, we may well be at the beginning of a novel direction in structure-property-activity studies that will be dominated by the use of variable molecular descriptors that not only lead to better regressions with fewer molecular descriptors in comparison with regressions using "fixed" descriptors, but, because variable descriptors offer novel interpretation to the descriptors [49], may also offer guidance in the refinement of molecular models, as will be explained later in this article.…”

Section: Flexible Molecular Descriptorsmentioning

confidence: 99%

Variable Connectivity Index as a Tool for Modeling Structure-Property Relationships

Randić

Pompe

Mills³

et al. 2004

Molecules

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Abstract:We report on the calculation of normal boiling points for a series of n = 58 aliphatic alcohols using the variable connectivity index in which variables x and y are used to modify the weights on carbon (x) and oxygen atoms (y) in molecular graphs, respectively. The optimal regressions are found for x = 0.80 and y = -0.90. Comparison is made with available regressions on the same data reported previously in the literature. A refinement of the model was considered by introducing different weights for primary, secondary, tertiary, and quaternary carbon atoms. The standard error in the case of the normal boiling points of alcohols was slightly reduced with optimal weights for different carbon atoms from s = 4.1°C (when all carbon atoms were treated as alike) to s = 3.9 °C.

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Section: Flexible Molecular Descriptorsmentioning

confidence: 99%

Variable Connectivity Index as a Tool for Modeling Structure-Property Relationships

Randić

Pompe

Mills³

et al. 2004

Molecules

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“…There are several versions of the optimal (flexible) descriptors [11][12][13][14][15][16][17][18][19][20]. The present study is based on the only SMILES based optimal descriptor [17][18][19][20].…”

Section: Methodsmentioning

confidence: 99%

SMILES in QSPR/QSAR Modeling: Results and Perspectives

Toropov¹,

Benfenati

2007

CDDT

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The technique of constructing optimal descriptors calculated with the Simplified molecular input line entry system (SMILES) is described. SMILES based optimal descriptors and descriptors calculated with molecular graphs (hydrogen filled graphs and graph of atomic orbitals) are compared in modeling done by means of quantitative structure - property/activity relationships (QSPR/QSAR). QSPR/QSAR models for normal boiling points of organic compounds, mutagenicity of heteroaromatic amines, toxicity, and anti-HIV-1 potentials of TIBO and HEPT derivatives are described in details. Possible ways to improve the SMILES based concept of QSPR/QSAR analyses are discussed.

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“…The optimal descriptors have been successfully used for the QSPR modeling of aliphatic alcohols [25], nitrogencontaining compounds [26], and sulfides [27]. Later on, optimal descriptors based on the hydrogen-filled graph have been suggested [28].…”

Section: Construction Of Optimal Descriptorsmentioning

confidence: 99%

OCWLGI Descriptors: Theory and Praxis

Toropov

Toropova

Benfenati

et al. 2013

CAD

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The aim of this review is description of the logic and evolution of optimal descriptors OCWLGI calculated with the molecular graph and the demonstration of their ability as tools for the modeling of biological and physicochemical parameters of chemical compounds. The ability of optimal descriptors calculated with hydrogen suppressed graph (HSG), hydrogen filled graph (HFG) and graph of atomic orbitals (GAO) is demonstrated as a collection of quantitative structure-property relationships (QSPR) and quantitative structure-activity relationships (QSAR) for properties and endpoints available from the literature. The Monte Carlo method optimization of the correlation weights of local and global invariants (OCWLGI) of molecular graphs is used as the principle for building up descriptors which are discussed in this article. The statistical quality of the QSPR and QSAR models for physicochemical and biological properties which were obtained with the optimal descriptors are reasonably high.

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Construction of High-Quality Structure−Property−Activity Regressions: The Boiling Points of Sulfides

Cited by 35 publications

References 40 publications

Variable Connectivity Index as a Tool for Modeling Structure-Property Relationships

Variable Connectivity Index as a Tool for Modeling Structure-Property Relationships

SMILES in QSPR/QSAR Modeling: Results and Perspectives

OCWLGI Descriptors: Theory and Praxis

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