Database Independent Automated Structure Elucidation of Organic Molecules Based on IR, 1H NMR, 13C NMR, and MS Data

Matevž Pesek; Andraž Juvan; Jure Jakoš; Janez Košmrlj; Matija Marolt; Martin Gazvoda

doi:10.1021/acs.jcim.0c01332

Database Independent Automated Structure Elucidation of Organic Molecules Based on IR, ¹H NMR, ¹³C NMR, and MS Data

J Chem Inf Model. 2021 Feb 22;61(2):756-763. doi: 10.1021/acs.jcim.0c01332. Epub 2020 Dec 30.

Authors

Matevž Pesek¹, Andraž Juvan¹, Jure Jakoš², Janez Košmrlj², Matija Marolt¹, Martin Gazvoda²

Affiliations

¹ Faculty of Computer and Information Science, University of Ljubljana, Večna Pot 113, SI-1000 Ljubljana, Slovenia.
² Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna Pot 113, SI-1000 Ljubljana, Slovenia.

Abstract

Herein, we report a computational algorithm that follows a spectroscopist-driven elucidation process of the structure of an organic molecule based on IR, ¹H and ¹³C NMR, and MS tabular data. The algorithm is independent from database searching and is based on a bottom-up approach, building the molecular structure from small structural fragments visible in spectra. It employs an analytical combinatorial approach with a graph search technique to determine the connectivity of structural fragments that is based on the analysis of the NMR spectra, to connect the identified structural fragments into a molecular structure. After the process is completed, the interface lists the compound candidates, which are visualized by the WolframAlpha computational knowledge engine within the interface. The candidates are ranked according to the predefined rules for analyzing the spectral data. The developed elucidator has a user-friendly web interface and is publicly available (http://schmarnica.si).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Algorithms*
Databases, Factual
Magnetic Resonance Spectroscopy
Molecular Structure
Proton Magnetic Resonance Spectroscopy