Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

15.4K
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...
15.4K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

5.3K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
5.3K
Chirality02:25

Chirality

30.4K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
30.4K
Fischer Projections02:18

Fischer Projections

16.9K
Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic molecules. A Fischer projection is a two-dimensional projection on a planar surface to simplify the three-dimensional wedge–dash representation of molecules. This is especially helpful in the case of molecules with multiple chiral centers that can be difficult to draw. Here, all the bonds of interest are represented as horizontal or vertical lines. While...
16.9K
Prochirality02:05

Prochirality

5.1K
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
5.1K
Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

7.1K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.1K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Ligand and structure-based discovery of phosphorus-containing compounds as potential metalloproteinase inhibitors.

SAR and QSAR in environmental research·2024
Same author

Exploring the QSAR's predictive truthfulness of the novel N-tuple discrete derivative indices on benchmark datasets.

SAR and QSAR in environmental research·2017
Same author

Allosteric modulation model of the mu opioid receptor by herkinorin, a potent not alkaloidal agonist.

Journal of computer-aided molecular design·2017
Same author

Discovering key residues of dengue virus NS2b-NS3-protease: New binding sites for antiviral inhibitors design.

Biochemical and biophysical research communications·2017
Same author

Conformation-dependent QSAR approach for the prediction of inhibitory activity of bromodomain modulators.

SAR and QSAR in environmental research·2017
Same author

N-tuple topological/geometric cutoffs for 3D N-linear algebraic molecular codifications: variability, linear independence and QSAR analysis.

SAR and QSAR in environmental research·2016

Related Experiment Video

Updated: Feb 26, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

8.5K

Tensor algebra-based geometric methodology to codify central chirality on organic molecules.

C R García-Jacas1,2,3, Y Marrero-Ponce4,5,6,7, T Hernández-Ortega3

  • 1a Instituto de Química, Universidad Nacional Autónoma de México (UNAM) , Ciudad de México , México.

SAR and QSAR in Environmental Research
|July 15, 2017
PubMed
Summary
This summary is machine-generated.

A new mathematical method enhances molecular vector weighting for chirality, improving QSAR model accuracy. This approach uses a broader range of correction factors beyond the typical 1/-1, leading to more robust predictions.

Keywords:
ChiralityN-alkylated 3-(3-hydroxyphenyl)-piperidinesQSARQuBiLS-MIDASTOMOCOMD-CARDDfenoterol stereoisomer derivativesperindoprilat stereoisomersstereochemistry

More Related Videos

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

11.0K
Author Spotlight: Unveiling the Potential of VSFG Microscopy in Studying Mesoscopically Heterogeneous Self-Assembled Structures
08:49

Author Spotlight: Unveiling the Potential of VSFG Microscopy in Studying Mesoscopically Heterogeneous Self-Assembled Structures

Published on: December 1, 2023

2.1K

Related Experiment Videos

Last Updated: Feb 26, 2026

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates
06:35

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

Published on: February 15, 2016

8.5K
Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

11.0K
Author Spotlight: Unveiling the Potential of VSFG Microscopy in Studying Mesoscopically Heterogeneous Self-Assembled Structures
08:49

Author Spotlight: Unveiling the Potential of VSFG Microscopy in Studying Mesoscopically Heterogeneous Self-Assembled Structures

Published on: December 1, 2023

2.1K

Area of Science:

  • Computational Chemistry
  • Cheminformatics
  • Quantitative Structure-Activity Relationship (QSAR) studies

Background:

  • Traditional methods for encoding molecular chirality in Quantitative Structure-Activity Relationship (QSAR) models often use a simplified binary system (1 and -1) for R/S stereocenters.
  • This binary approach may limit the ability to capture the nuanced impact of stereochemistry on molecular properties and biological activity.
  • Existing QSAR models based on classical QuBiLS-MIDAS descriptors can be enhanced by incorporating more sophisticated chirality descriptors.

Purpose of the Study:

  • To introduce a novel mathematical procedure for codifying chiral features of organic molecules within the QuBiLS-MIDAS framework.
  • To generalize the weighting of molecular vectors beyond the conventional 1/-1 correction factors.
  • To demonstrate the feasibility and advantages of using a wider range of correction factors for chirality encoding in QSAR modeling.

Main Methods:

  • Developed a generalized mathematical procedure to assign real number values (in the range [-3, 3] with 0.25 steps) as correction factors for R/S labeled atoms.
  • Introduced 'Chiral QuBiLS-MIDAS 3D-Molecular Descriptors' (3D-MDs) that can be non-symmetric and reduced to classical descriptors when symmetry is not codified.
  • Applied these novel descriptors in QSAR modeling on four diverse chemical datasets, focusing on factors with opposed values.

Main Results:

  • QSAR models built using the novel Chiral QuBiLS-MIDAS 3D-MDs with multiple correction factors demonstrated superior robustness and predictive ability.
  • Performance improvements were observed compared to models using only the classical 1/-1 correction factor and existing literature models.
  • The feasibility of the proposed method was successfully demonstrated across four distinct chemical datasets.

Conclusions:

  • The novel strategy for codifying chirality offers a significant advancement over traditional methods for computing chirality-based descriptors.
  • This approach provides a suitable alternative for developing QSAR models with enhanced predictive power for symmetry-dependent properties.
  • The generalized correction factors allow for a more nuanced representation of stereochemical information in molecular descriptors.