Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
| Autor: | Piercosimo Tripaldi, Pablo R. Duchowicz, Reinaldo Pis Diez, Cristian Rojas |
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| Jazyk: | angličtina |
| Rok vydání: | 2015 |
| Předmět: |
Quantitative structure–activity relationship
Chromatography Gas Molecular Conformation Quantitative Structure-Activity Relationship Biochemistry Chemistry Techniques Analytical Analytical Chemistry FRAGRANCE Molecular descriptor Chromatography QSPR THEORY Chemistry Otras Ciencias Químicas Organic Chemistry Linear model Ciencias Químicas Reproducibility of Results General Medicine K-MEANS CLUSTER ANALYSIS Models Theoretical Perfume Flavoring Agents Distance matrix Topological index Test set CARBOWAX 20M COLUMN Linear Models Kovats retention index DRAGON SOFTWARE REPLACEMENT METHOD Software CIENCIAS NATURALES Y EXACTAS Applicability domain |
| Popis: | A quantitative structure-property relationship (QSPR) was developed for modeling the retention index of 1184 flavor and fragrance compounds measured using a Carbowax 20M glass capillary gas chromatography column. The 4885 molecular descriptors were calculated using Dragon software, and then were simultaneously analyzed through multivariable linear regression analysis using the replacement method (RM) variable subset selection technique. We proceeded in three steps, the first one by considering all descriptor blocks, the second one by excluding conformational descriptor blocks, and the last one by analyzing only 3D-descriptor families. The models were validated through an external test set of compounds. Cross-validation methods such as leave-one-out and leave-many-out were applied, together with Y-randomization and applicability domain analysis. The developed model was used to estimate the I of a set of 22 molecules. The results clearly suggest that 3D-descriptors do not offer relevant information for modeling the retention index, while a topological index such as the Randić-like index from reciprocal squared distance matrix has a high relevance for this purpose. Fil: Rojas Villa, Cristian Xavier. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina. Universidad del Azuay; Ecuador Fil: Duchowicz, Pablo Román. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas; Argentina Fil: Tripaldi, Piercosimo. Universidad del Azuay; Ecuador Fil: Pis Diez, Reinaldo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina |
| Databáze: | OpenAIRE |
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