使用深度对比学习进行化合物识别的 13C NMR 谱和结构之间的交叉模式检索,Analytical Chemistry

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使用深度对比学习进行化合物识别的 13C NMR 谱和结构之间的交叉模式检索
Analytical Chemistry ( IF 6.7 ) Pub Date : 2021-11-29 , DOI: 10.1021/acs.analchem.1c04307
Zhuo Yang ₁ , Jianfei Song ₂ , Minjian Yang ₁ , Lin Yao ₂ , Jiahua Zhang ₂ , Hui Shi ₃ , Xiangyang Ji ₄ , Yafeng Deng _{2,

4} , Xiaojian Wang ₁

Affiliation

使用碳 13 核磁共振 ( ¹³ C NMR) 光谱进行库匹配已成为化合物识别系统中常用的方法。然而，现有方法的可用性受到限制，因为扩大包含化学结构和光谱的库是一个昂贵且耗时的过程。因此，我们提出了一种完全不同的新颖方法，将¹³ C NMR 光谱直接与分子结构库进行匹配。我们使用深度对比学习开发了光谱和结构之间的跨模式检索 (CReSS) 系统，这使我们能够使用化合物的¹³ C NMR 光谱搜索分子结构库。搜索测试中 41,494 ¹³C NMR 谱针对包含 1040 万个化合物的参考结构库，CReSS 达到了 91.64% 的召回@10 准确度和每个查询谱 0.114 秒的处理速度。当进一步加入分子量耐受为 5 Da 的过滤器时，CReSS 实现了 98.39% 的新的显着召回@10。此外，CReSS 具有检测新型结构支架的潜力，并在结构修正任务中表现出出色的性能。CReSS 的构建和开发旨在弥合¹³ C NMR 光谱和结构之间的差距，可普遍适用于化合物鉴定。

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Cross-Modal Retrieval between 13C NMR Spectra and Structures for Compound Identification Using Deep Contrastive Learning

Library matching using carbon-13 nuclear magnetic resonance (¹³C NMR) spectra has been a popular method adopted in compound identification systems. However, the usability of existing approaches has been restricted as enlarging a library containing both a chemical structure and spectrum is a costly and time-consuming process. Therefore, we propose a fundamentally different, novel approach to match ¹³C NMR spectra directly against a molecular structure library. We develop a cross-modal retrieval between spectrum and structure (CReSS) system using deep contrastive learning, which allows us to search a molecular structure library using the ¹³C NMR spectrum of a compound. In the test of searching 41,494 ¹³C NMR spectra against a reference structure library containing 10.4 million compounds, CReSS reached a recall@10 accuracy of 91.64% and a processing speed of 0.114 s per query spectrum. When further incorporating a filter with a molecular weight tolerance of 5 Da, CReSS achieved a new remarkable recall@10 of 98.39%. Furthermore, CReSS has potential in detecting scaffolds of novel structures and demonstrates great performance for the task of structural revision. CReSS is built and developed to bridge the gap between ¹³C NMR spectra and structures and could be generally applicable in compound identification.

更新日期：2021-12-21

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