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Related Concept Videos

Chirality02:25

Chirality

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...
Molecules with Multiple Chiral Centers02:25

Molecules with Multiple Chiral Centers

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...
Chirality in Nature02:30

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...
Prochirality02:05

Prochirality

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...
Stereoisomers02:32

Stereoisomers

On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to restricted...
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...

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Related Experiment Video

Updated: Jun 19, 2026

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

Molecular similarity including chirality.

M Stuart Armstrong1, Garrett M Morris, Paul W Finn

  • 1InhibOx, Pembroke House, Oxford OX1 1BP, UK.

Journal of Molecular Graphics & Modelling
|October 6, 2009
PubMed
Summary
This summary is machine-generated.

Chiral Shape Recognition (CSR) is a new method for molecular similarity that can differentiate enantiomers. CSR shows improved performance over Ultra-fast Shape Recognition (USR) in drug discovery screening.

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Area of Science:

  • Computational chemistry
  • Cheminformatics
  • Drug discovery

Background:

  • Molecular similarity is crucial for drug discovery and virtual screening.
  • Existing methods like Ultra-fast Shape Recognition (USR) do not effectively distinguish between enantiomers.
  • Enantiomers can have different biological activities and toxicities.

Purpose of the Study:

  • To introduce Chiral Shape Recognition (CSR), a novel method for computing molecular similarity.
  • To enhance molecular screening by enabling the differentiation of enantiomers.
  • To evaluate the performance of CSR compared to USR.

Main Methods:

  • CSR builds upon the Ultra-fast Shape Recognition (USR) algorithm.
  • The method incorporates chirality to distinguish between enantiomers.
  • Performance was assessed using the DUD dataset for virtual screening.

Main Results:

  • CSR demonstrated significant improvements in enrichment compared to USR.
  • The method showed enhanced performance when screening the top 0.25%, 0.5%, and 1% of the database.
  • CSR effectively distinguishes enantiomers, a key advantage over USR.

Conclusions:

  • CSR is a promising method for molecular similarity computation, particularly for distinguishing enantiomers.
  • The method offers significant potential for generalization in drug discovery applications.
  • CSR represents a valuable advancement for virtual screening and lead identification.