Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase

Autores
Rojas Villa, Cristian Xavier; Duchowicz, Pablo Román; Tripaldi, Piercosimo; Pis Diez, Reinaldo
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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
Materia
Carbowax 20m Column
Dragon Software
Fragrance
K-Means Cluster Analysis
Qspr Theory
Replacement Method
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48829
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/48829
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phaseRojas Villa, Cristian XavierDuchowicz, Pablo RománTripaldi, PiercosimoPis Diez, ReinaldoCarbowax 20m ColumnDragon SoftwareFragranceK-Means Cluster AnalysisQspr TheoryReplacement Methodhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A 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; EcuadorFil: 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; ArgentinaFil: Tripaldi, Piercosimo. Universidad del Azuay; EcuadorFil: 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"; ArgentinaElsevier Science2015-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48829Rojas Villa, Cristian Xavier; Duchowicz, Pablo Román; Tripaldi, Piercosimo; Pis Diez, Reinaldo; Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase; Elsevier Science; Journal of Chromatography - A; 1422; 11-2015; 277-2880021-9673CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2015.10.028info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0021967315014867info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:56:27Zoai:ri.conicet.gov.ar:11336/48829instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:56:27.464CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
title Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
spellingShingle Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
Rojas Villa, Cristian Xavier
Carbowax 20m Column
Dragon Software
Fragrance
K-Means Cluster Analysis
Qspr Theory
Replacement Method
title_short Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
title_full Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
title_fullStr Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
title_full_unstemmed Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
title_sort Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase
dc.creator.none.fl_str_mv Rojas Villa, Cristian Xavier
Duchowicz, Pablo Román
Tripaldi, Piercosimo
Pis Diez, Reinaldo
author Rojas Villa, Cristian Xavier
author_facet Rojas Villa, Cristian Xavier
Duchowicz, Pablo Román
Tripaldi, Piercosimo
Pis Diez, Reinaldo
author_role author
author2 Duchowicz, Pablo Román
Tripaldi, Piercosimo
Pis Diez, Reinaldo
author2_role author
author
author
dc.subject.none.fl_str_mv Carbowax 20m Column
Dragon Software
Fragrance
K-Means Cluster Analysis
Qspr Theory
Replacement Method
topic Carbowax 20m Column
Dragon Software
Fragrance
K-Means Cluster Analysis
Qspr Theory
Replacement Method
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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
description 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.
publishDate 2015
dc.date.none.fl_str_mv 2015-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/48829
Rojas Villa, Cristian Xavier; Duchowicz, Pablo Román; Tripaldi, Piercosimo; Pis Diez, Reinaldo; Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase; Elsevier Science; Journal of Chromatography - A; 1422; 11-2015; 277-288
0021-9673
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48829
identifier_str_mv Rojas Villa, Cristian Xavier; Duchowicz, Pablo Román; Tripaldi, Piercosimo; Pis Diez, Reinaldo; Quantitative structure-property relationship analysis for the retention index of fragrance-like compounds on a polar stationary phase; Elsevier Science; Journal of Chromatography - A; 1422; 11-2015; 277-288
0021-9673
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chroma.2015.10.028
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0021967315014867
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science
publisher.none.fl_str_mv Elsevier Science
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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