Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives

The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic na...

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Main Authors: Janairo, Jose Isagani B., Janairo, Gerardo C., Yu, Derrick Ethelbhert C.
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Published: Animo Repository 2011
Online Access:https://animorepository.dlsu.edu.ph/faculty_research/1133
https://animorepository.dlsu.edu.ph/context/faculty_research/article/2132/type/native/viewcontent
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spelling oai:animorepository.dlsu.edu.ph:faculty_research-21322022-07-28T07:35:16Z Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives Janairo, Jose Isagani B. Janairo, Gerardo C. Yu, Derrick Ethelbhert C. The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic nature can result to poor bioavailabilty, low absorption and poor systemic circulation. In silico simulations revealed that this setback can be overcome by introduction of hydroxyl group to the tertiary carbon of entkaurenoic acid employing m-CPBA catalyzed hydroxylation, thus, unleashing its full drug potency. Moreover, molecular similarity analyses derived from semi-empirical calculations between ent-kaurenoic acid and a set of kaurane diterpenoids showed differences in hydrophobic complementarity, size and electronic properties despite possessing nearly identical molecular frameworks, thus, arriving in a generalization for their observed mechanistic differences on acting on different targets. 2011-01-01T08:00:00Z text text/html https://animorepository.dlsu.edu.ph/faculty_research/1133 https://animorepository.dlsu.edu.ph/context/faculty_research/article/2132/type/native/viewcontent Faculty Research Work Animo Repository
institution De La Salle University
building De La Salle University Library
continent Asia
country Philippines
Philippines
content_provider De La Salle University Library
collection DLSU Institutional Repository
description The physicochemical properties of ent- kaurenoic acid model derivatives, which possibly influence its therapeutic application, were calculated. Results revealed that the molecule possess favourable attributes which renders it possible to be considered as a drug lead only that its very hydrophobic nature can result to poor bioavailabilty, low absorption and poor systemic circulation. In silico simulations revealed that this setback can be overcome by introduction of hydroxyl group to the tertiary carbon of entkaurenoic acid employing m-CPBA catalyzed hydroxylation, thus, unleashing its full drug potency. Moreover, molecular similarity analyses derived from semi-empirical calculations between ent-kaurenoic acid and a set of kaurane diterpenoids showed differences in hydrophobic complementarity, size and electronic properties despite possessing nearly identical molecular frameworks, thus, arriving in a generalization for their observed mechanistic differences on acting on different targets.
format text
author Janairo, Jose Isagani B.
Janairo, Gerardo C.
Yu, Derrick Ethelbhert C.
spellingShingle Janairo, Jose Isagani B.
Janairo, Gerardo C.
Yu, Derrick Ethelbhert C.
Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
author_facet Janairo, Jose Isagani B.
Janairo, Gerardo C.
Yu, Derrick Ethelbhert C.
author_sort Janairo, Jose Isagani B.
title Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
title_short Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
title_full Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
title_fullStr Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
title_full_unstemmed Semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
title_sort semi-empirical predictions on the structure and properties of ent-kaurenoic acid and derivatives
publisher Animo Repository
publishDate 2011
url https://animorepository.dlsu.edu.ph/faculty_research/1133
https://animorepository.dlsu.edu.ph/context/faculty_research/article/2132/type/native/viewcontent
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