Abstract
AbstractHomologous series are groups of related compounds that share the same core structure attached to a motif that repeats to different degrees. Compounds forming homologous series are of interest in multiple domains, including natural products, environmental chemistry, and drug design. However, many homologous compounds remain unannotated as such in compound datasets, which poses obstacles to understanding chemical diversity and their analytical identification via database matching. To overcome these challenges, an algorithm to detect homologous series within compound datasets was developed and implemented using the RDKit. The algorithm takes a list of molecules as SMILES strings and a monomer (i.e., repeating unit) encoded as SMARTS as its main inputs. In an iterative process, substructure matching of repeating units, molecule fragmentation, and core detection lead to homologous series classification through grouping of identical cores. Three open compound datasets from environmental chemistry (NORMAN Suspect List Exchange, NORMAN-SLE), exposomics (PubChemLite for Exposomics), and natural products (the COlleCtion of Open NatUral producTs, COCONUT) were subject to homologous series classification using the algorithm. Over 2000, 12,000, and 5000 series with CH2 repeating units were classified in the NORMAN-SLE, PubChemLite, and COCONUT respectively. Validation of classified series was performed using published homologous series and structure categories, including a comparison with a similar existing method for categorising PFAS compounds. The OngLai algorithm and its implementation for classifying homologues are openly available at: https://github.com/adelenelai/onglai-classify-homologues.
Funder
Fonds National de la Recherche Luxembourg
Carl-Zeiss-Stiftung
Friedrich-Schiller-Universität Jena
Publisher
Springer Science and Business Media LLC
Subject
Library and Information Sciences,Computer Graphics and Computer-Aided Design,Physical and Theoretical Chemistry,Computer Science Applications
Reference83 articles.
1. Markush EA (1924) Pyrazolone Dye and Process of Making the Same. USA101506316, August 26, 1924. https://pdfpiw.uspto.gov/.piw?PageNum=USA101506316&docid=01506316&IDKey=83E682D73B35&HomeUrl=http%3A%2F%2Fpatft.uspto.gov%2Fnetacgi%2Fnph-Parser%3FSect1%3DPTO1%2526Sect2%3DHITOFF%2526p%3D1%2526u%3D%2Fnetahtml%2FPTO%2Fsrchnum.html%2526r%3D1%2526f%3DG%2526l%3D50%2526d%3DPALL%2526s1%3D1506316.PN.%2526OS%3D%2526RS%3D . Accessed 25 Mar 2022
2. Lima LM, Alves MA, Amaral DN (2019) Homologation: a versatile molecular modification strategy to drug discovery. Curr Top Med Chem. 19:1734–1750. https://doi.org/10.2174/1568026619666190808145235
3. Niemczak M, Rzemieniecki T, Sobiech Ł, Skrzypczak G, Praczyk T, Pernak J (2019) Influence of the alkyl chain length on the physicochemical properties and biological activity in a homologous series of dichlorprop-based herbicidal ionic liquids. J Mol Liq 276:431–440. https://doi.org/10.1016/j.molliq.2018.12.013
4. Zhu J-P, Liang M-Y, Ma Y-R, White LV, Banwell MG, Teng Y, Lan P (2022) Enzymatic synthesis of an homologous series of long- and very long-chain sucrose esters and evaluation of their emulsifying and biological properties. Food Hydrocoll 124:107149. https://doi.org/10.1016/j.foodhyd.2021.107149
5. Wolf SE, Liu T, Govind S, Zhao H, Huang G, Zhang A, Wu Y, Chin J, Cheng K, Salami-Ranjbaran E, Gao F, Gao G, Jin Y, Pu Y, Toledo TG, Ablajan K, Walsh PJ, Fakhraai Z (2021) Design of a homologous series of molecular glassformers. J Chem Phys 155(22):224503. https://doi.org/10.1063/5.0066410
Cited by
1 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献