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Related Concept Videos

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...
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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,...
Modern Molecular Taxonomy01:29

Modern Molecular Taxonomy

Advancements in molecular biology have revolutionized the identification and characterization of bacteria, with multiple methods leveraging DNA sequencing for enhanced precision. As sequencing technologies improve and costs decline, these approaches are increasingly used in clinical, environmental, and evolutionary studies.Multilocus Sequence Typing (MLST) examines several housekeeping genes, essential chromosomal genes encoding cellular functions, to distinguish strains. Approximately...
Fischer Projections02:18

Fischer Projections

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...

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Comprehensive Spatial Profiling of Species-agnostic Transcriptomes via Stereo-seq
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Published on: October 31, 2025

Stereo signature molecular descriptor.

Pablo Carbonell1, Lars Carlsson, Jean-Loup Faulon

  • 1University of Evry, CNRS, Institute of Systems and Synthetic Biology, Évry, France. pablo.carbonell@issb.genopole.fr

Journal of Chemical Information and Modeling
|March 27, 2013
PubMed
Summary

We developed a new algorithm for computing molecular graph descriptors that accurately accounts for stereochemistry. This method improves predictions of bioactivity and models stereoselective reactions, outperforming existing descriptors.

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Area of Science:

  • Computational chemistry
  • Cheminformatics
  • Molecular modeling

Background:

  • Molecular descriptors are crucial for predicting chemical properties and bioactivity.
  • Accurately representing stereochemistry in molecular descriptors is challenging but essential for understanding molecular interactions.
  • Existing methods may not fully capture complex stereochemical information.

Purpose of the Study:

  • To introduce a novel algorithm for generating molecular graph descriptors that incorporate stereochemistry.
  • To develop descriptors compliant with Cahn-Ingold-Prelog rules and computationally efficient alternatives.
  • To evaluate the performance of these stereo-aware descriptors in canonicalization and bioactivity prediction.

Main Methods:

  • An algorithm was developed based on the signature molecular descriptor concept.
  • The algorithm generates two types of descriptors: one adhering to Cahn-Ingold-Prelog rules for complex structures, and a computationally efficient version using augmented chiral graphs.
  • Performance was assessed for speed as a canonicalizer and for modeling bioactivity.

Main Results:

  • The algorithm successfully generates stereochemically relevant molecular descriptors.
  • The new descriptors demonstrate superior performance in bioactivity modeling and prediction compared to other methods.
  • The approach is particularly effective for modeling stereoselective biochemical reactions.

Conclusions:

  • The stereo signature molecular descriptor algorithm provides an effective way to incorporate stereochemistry into molecular representations.
  • This method enhances the accuracy of molecular modeling, especially for stereoselective processes.
  • The open-source availability facilitates broader adoption and further research in the field.