ArticleMetabolomics : Official journal of the Metabolomic Society
A 'rule of 0.5' for the metabolite-likeness of approved pharmaceutical drugs.
Article in Metabolomics : Official journal of the Metabolomic Society. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 51 papers.
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Who cites it
51 citing papers in PubMed.
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- Anticoronavirus Isoquinoline Alkaloids: Unraveling the Secrets of Their Structure-Activity Relationship.Influenza and other respiratory viruses · 2025Article
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- Decoding the Knacks of Ellagitannin Lead Compounds to Treat Nonalcoholic Fatty Liver Disease using Computer-aided Drug Designing.Current computer-aided drug design · 2025Article
- The Biology and Biochemistry of Kynurenic Acid, a Potential Nutraceutical with Multiple Biological Effects.International journal of molecular sciences · 2024Review
- Do Molecular Fingerprints Identify Diverse Active Drugs in Large-Scale Virtual Screening? (No).Pharmaceuticals (Basel, Switzerland) · 2024Article
- Evidence for the Role of the Mitochondrial ABC Transporter MDL1 in the Uptake of Clozapine and Related Molecules into the YeastPharmaceuticals (Basel, Switzerland) · 2024Article
- Occurrence of "Natural Selection" in Successful Small Molecule Drug Discovery.Journal of medicinal chemistry · 2024Article
- Lead generation of UPPS inhibitors targeting MRSA: Using 3D-QSAR pharmacophore modeling, virtual screening, molecular docking, and molecular dynamic simulations.BMC chemistry · 2024Article
- Artificial intelligence-powered discovery of small molecules inhibiting CTLA-4 in cancer.BJC reports · 2024Article
- Synthesis of Metabolites and Metabolite-like Compounds Using Biocatalytic Systems.Metabolites · 2023Review
- Analysis of metabolites in human gut: illuminating the design of gut-targeted drugs.Journal of cheminformatics · 2023Article
- The Time and Place for Nature in Drug Discovery.JACS Au · 2022Review
- Palladium(II) Complexes of Substituted Salicylaldehydes: Synthesis, Characterization and Investigation of Their Biological Profile.Pharmaceuticals (Basel, Switzerland) · 2022Article
- Relative Binding Free Energy between Chemically Distant Compounds Using a Bidirectional Nonequilibrium Approach.Journal of chemical theory and computation · 2022Article
- Bioactivity assessment of natural compounds using machine learning models trained on target similarity between drugs.PLoS computational biology · 2022Article
- Natural product drug discovery in the artificial intelligence era.Chemical science · 2022Review
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
We exploit the recent availability of a community reconstruction of the human metabolic network ('Recon2') to study how close in structural terms are marketed drugs to the nearest known metabolite(s) that Recon2 contains. While other encodings using different kinds of chemical fingerprints give greater differences, we find using the 166 Public MDL Molecular Access (MACCS) keys that 90 % of marketed drugs have a Tanimoto similarity of more than 0.5 to the (structurally) 'nearest' human metabolite. This suggests a 'rule of 0.5' mnemonic for assessing the metabolite-like properties that characterise successful, marketed drugs. Multiobjective clustering leads to a similar conclusion, while artificial (synthetic) structures are seen to be less human-metabolite-like. This 'rule of 0.5' may have considerable predictive value in chemical biology and drug discovery, and may represent a powerful filter for decision making processes.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.