Current complexity: a tool for assessing the complexity of organic molecules.

@article{Li2015CurrentCA,
  title={Current complexity: a tool for assessing the complexity of organic molecules.},
  author={Jun Li and Martin D. Eastgate},
  journal={Organic \& biomolecular chemistry},
  year={2015},
  volume={13 26},
  pages={
          7164-76
        }
}
Molecular complexity for a synthetic organic chemist is difficult to define, though intuitively known. Despite the importance of this concept, the quantitative assessment of complexity within organic chemistry has remained a challenge. We report here on the development of an approach for generating a unique complexity index, which is reflective of both intrinsic molecular complexity and extrinsic synthetic complexity. This index is based on a community's perception of complexity, within the… 

Figures and Tables from this paper

An Additive Definition of Molecular Complexity
TLDR
This approach may provide a useful tool for medicinal chemistry in drug design and lead selection, as demonstrated by correlating molecular complexities of antibiotics with compound-specific parameters.
A path based approach to assessing molecular complexity.
  • J. Proudfoot
  • Chemistry
    Bioorganic & medicinal chemistry letters
  • 2017
Identifying molecules as biosignatures with assembly theory and mass spectrometry
TLDR
This work shows why complex molecules found in high abundance are universal biosignatures and demonstrates the first intrinsic experimentally tractable measure of molecular complexity, called the molecular assembly index (MA), and calculates the complexity of several million molecules and validate that their complexity can be experimentally determined by mass spectrometry.
SCScore: Synthetic Complexity Learned from a Reaction Corpus
TLDR
This work trains a neural network model on 12 million reactions from the Reaxys database to impose a pairwise inequality constraint enforcing the premise: that on average, the products of published chemical reactions should be more synthetically complex than their corresponding reactants.
Molecular Complexity and Retrosynthesis.
TLDR
An atom-environment complexity measure, CA, to assess local changes in complexity during synthetic transformations is described, which varies with expectation across a number of basic reaction examples and may identify the key disconnections to guide retrosynthesis.
On the design of complex drug candidate syntheses in the pharmaceutical industry
TLDR
This Review argues that achieving this goal requires visionary retrosynthetic strategy and is tightly linked to the discovery and development of new reactions and novel processes, and the tactics used during the design and selection of an efficient drug synthesis.
The Rise and Fall of a Scaffold: A Trend Analysis of Scaffolds in the Medicinal Chemistry Literature.
TLDR
Trend analyses of scaffold properties could support scaffold selection and prioritization in small molecule development projects and explain why a scaffold receives more attention over time.
Sustainable Practices in Medicinal Chemistry Part 2: Green by Design.
TLDR
Multiple cheminformatic approaches in drug discovery that can influence and triage design and execution impacting the likelihood of rapidly generating high-value molecules in a more sustainable manner are highlighted.
Natural Products in the "Marketplace": Interfacing Synthesis and Biology.
TLDR
Past examples of NP analogue development and successful NP-derived drugs are highlighted, including studies of how NP analogues alter the retrosynthetic analysis of complex scaffolds, merging structural design and synthetic design.
...
1
2
3
4
5
...

References

SHOWING 1-10 OF 53 REFERENCES
Complex molecules: do they add value?
The importance of molecular complexity in the design of screening libraries
TLDR
It is hypothesized that molecules of lower complexity are preferred for target based screening campaigns, while augmenting such a library with moieties of moderate complexities maybe better suited for phenotypic screens.
Estimation of synthetic accessibility score of drug-like molecules based on molecular complexity and fragment contributions
TLDR
This method uses historical synthetic knowledge obtained by analyzing information from millions of already synthesized chemicals and considers also molecule complexity, which is sufficiently fast and provides results consistent with estimation of ease of synthesis by experienced medicinal chemists.
Molecular complexity analysis of de novo designed ligands.
TLDR
A novel method for complexity analysis that takes place at various levels of abstraction, so that it can evaluate complexity scores, even for structures which contain atoms with unspecified atom type, which is sometimes the case with the initial output of de novo structure generation systems.
Structure and reaction based evaluation of synthetic accessibility
TLDR
A scoring method is devised that rapidly evaluates synthetic accessibility of structures based on structural complexity, similarity to available starting materials and assessment of strategic bonds where a structure can be decomposed to obtain simpler fragments.
Molecular complexity: a simplified formula adapted to individual atoms
TLDR
A simple program in FORTRAN for microcomputer which yields the same values as Bertz's formulas for calculating molecular complexity, well adapted for use in locating synthesis pathways with least molecular complexity in the synthesis program.
A New and Simple Approach to Chemical Complexity. Application to the Synthesis of Natural Products
TLDR
A new approach to describe the complexity of chemical structures is proposed, which derives from Whitlock's index and provides results paralleling those obtained with the mathematical Bertz index.
On the Structure of Total Synthesis of Complex Natural Products
A chemically intuitive measure (metric) for molecular complexity is described. It is then applied to several syntheses of complex natural products. We conclude that the metric corresponds well with
Assessing Synthetic Accessibility of Chemical Compounds Using Machine Learning Methods
TLDR
Two approaches to quickly predict the synthetic accessibility of chemical compounds by utilizing support vector machines operating on molecular descriptors are presented and shown to perform well in their corresponding areas of applicability.
Collective synthesis of natural products by means of organocascade catalysis
TLDR
It is shown that the application of two nature-inspired techniques, namely organocascade catalysis and collective natural product synthesis, can facilitate the preparation of useful quantities of a range of structurally diverse natural products from a common molecular scaffold.
...
1
2
3
4
5
...