文章基本信息

标题：STOUT: SMILES to IUPAC names using neural machine translation
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作者：Kohulan Rajan ; Achim Zielesny ; Christoph Steinbeck 等
期刊名称：Journal of Cheminformatics
印刷版ISSN：1758-2946
电子版ISSN：1758-2946
出版年度：2021
卷号：13
期号：1
页码：1-14
DOI：10.1186/s13321-021-00512-4
出版社：BioMed Central
摘要：Chemical compounds can be identified through a graphical depiction, a suitable string representation, or a chemical name. A universally accepted naming scheme for chemistry was established by the International Union of Pure and Applied Chemistry (IUPAC) based on a set of rules. Due to the complexity of this ruleset a correct chemical name assignment remains challenging for human beings and there are only a few rule-based cheminformatics toolkits available that support this task in an automated manner. Here we present STOUT (SMILES-TO-IUPAC-name translator), a deep-learning neural machine translation approach to generate the IUPAC name for a given molecule from its SMILES string as well as the reverse translation, i.e. predicting the SMILES string from the IUPAC name. In both cases, the system is able to predict with an average BLEU score of about 90% and a Tanimoto similarity index of more than 0.9. Also incorrect predictions show a remarkable similarity between true and predicted compounds.
关键词：Neural machine translation ; Chemical language ; IUPAC names ; SMILES ; DeepSMILES ; SELFIES ; Deep neural network ; Attention mechanism ; Recurrent neural network