A Systematic Cheminformatics Analysis of Functional Groups Occurring in Natural Products
Abstract
The two most striking features that discriminate natural products from synthetic molecules are their characteristic scaffolds and unique functional groups (FGs). In this study we systematically investigate the distribution of FGs in natural products from a cheminformatics perspective by comparing FG frequencies in natural products with those found in average synthetic molecules. We thereby aim for the identification of FGs that are characteristic for molecules produced by living organisms. In our analysis we also include information about the natural origins of the structures investigated, allowing us to link the occurrence of specific FGs to the individual producing species. Our findings have the potential for being applied in a medicinal chemistry context concerning the synthesis of natural product-like libraries and natural product-inspired fragment collections. The results may be used also to support compound derivatization strategies and the design of "non-natural" natural products.
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Ertl and Schuhmann conducted a chemoinformatic investigation of the NPs chemical space.
“To this end, Ertl and Schuhmann, recently conducted a chemoinformatic investigation of the NPs chemical space.94”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [94]
The concept of functional groups is central to research fields such as medicinal chemistry, ecology, or toxicology.
“Thus, the concept of functional groups is central to research fields such as medicinal chemistry, ecology, or toxicology, among others.94”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [94]
Functional groups such as hydroxyl group, phenols, ketones, aldehydes, carboxylic acids, alkenes, dienes and Michael-acceptors were the most common functional groups among NPs.
“Functional groups such as hydroxyl group, phenols, ketones, aldehydes, carboxylic acids, alkenes, dienes and Michael-acceptors, were the most common functional groups among NPs.”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [94]
Over 260,000 NPs from the richest databases were inspected, and 2785 unique functional groups were retrieved.
“Over 260 000 NPs from the richest databases (DNP, Natural Product Atlas, TCM Database) were inspected, and 2785 unique functional groups were retrieved.”
From Connecting metabolome and phenotype: recent advances in functional metabolomics tools for the identification of bioactive natural products (2024) · cites this paper as [94]
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- Authors
- Ertl, P., & Schuhmann, T.
- Affiliations
- Novartis (Switzerland) (CH)
- Corresponding author
- Ertl, Peter
- Venue
- Journal of Natural Products
- Publisher
- American Chemical Society (ACS)
- Published
- 2019-04-01
- Volume
- 82
- Issue
- 5
- Pages
- 1258-1263
- ISSN
- 0163-3864 (ISSN-L)
- 1520-6025
- OpenAlex
- W2933530798
- Cited by
- 358
- References
- 28
- Citations by year
- 2026: 67 · 2025: 89 · 2024: 67 · 2023: 57 · 2022: 37 · 2021: 17 · 2020: 16 · 2019: 8
- FWCI
- 13.24
- Type
- journal article
- Language
- en
- Open access
- closed
- Licence
- Locations
- Journal of Natural Products (publishedVersion)
- PubMed (publishedVersion)
- The Novartis Repository (Novartis) (submittedVersion)
- Topics
- Physical Sciences › Computer Science › Computational Theory and Mathematics › Computational Drug Discovery Methods
- Health Sciences › Medicine › Pharmacology › Microbial Natural Products and Biosynthesis
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Bioactive natural compounds
- Keywords
- functional groups, natural products, synthetic compounds, natural product scaffolds, cheminformatics
- MeSH terms
- Cheminformatics, Biological Products, Structure-Activity Relationship, Molecular Structure, Computational Biology, Combinatorial Chemistry Techniques
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