Large Virtual Enhancement of a <sup>13</sup>C NMR Database. A Structural Crowning Extrapolation Method Enabling Spectral Data Transfer

Carabédian, Michel; Dubois, Jacques-Émile

doi:10.1021/ci970024y

Cited by 5 publications

(1 citation statement)

References 11 publications

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“…The immediate consequence of the utilization of this system on the structure generator will be the reduction of computational time and of the number of displayed structural proposals, hence avoiding the combinatorial explosion problem observed in other expert systems developed up to now (9,11,12,56,57).…”

Section: Discussionmentioning

confidence: 99%

MONOREG an expert system for structural elucidation of monoterpenes

Ferreira¹,

Rodrigues²,

Emerenciano³

2001

Can. J. Chem.

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This paper describes a new expert system denominated MONOREG for structural determination of monoterpenes. This system is composed of five programs capable of performing 13 C NMR spectra data analyses and analyses of systematic data from living organisms. At the end of this procedure, it shows the likely skeletons of the compound in question as well as the substructures compatible with the 13 C NMR data. The system was tested on the skeleton elucidation of 40 monoterpenes from a wide variety of structure types and exhibited excellent results in the skeleton prediction process.Résumé : Cet article décrit un nouveau système expert, dénommé MONOREG, utilisé pour la détermination structurale des monoterpènes. Ce système se compose de cinq programmes qui réalisent l'analyse RMN du 13 C d'un composé et utilize aussi des données de systématiques d'organismes vivants. Les squelettes probables sont déterminés ainsi que les sous-structures compatibles avec les données spectrales. Le système a été testé pour l'élucidation de 40 monoterpènes qui appartiennent à divers types de squelettes, et montre d'excellents résultats.Mots clés : monoterpènes, RMN du 13 C, élucidation structurale, analyse assisteé par ordinateur, système expert. Ferreira et al. 1925The MONOREG system MONOREG is a system that performs data analyses of monoterpenes. The idea for this name comes from the Portuguese words monoterpenos (Engl., monoterpenes) and regras (Engl. rules). Basically, this system is composed of five programs: MACRONO, SISCONST, C13MACH, SISOCBOT, Can. ). and REGRAS, which propose, at the end of analysis, a probable skeleton compatible with the entered data. This system is also capable of carrying out analyses of data from MS, however, these data were not inserted in the system. Therefore, they were not evaluated. The programs mentioned above are described below. The MACRONO programThe MACRONO program (22, 23) identifies the common substituent groups present in the natural products, such as acetate, angelate, tiglate. From the 13 C NMR chemical shifts and respective multiplicities of the substance in question, the program searches the database for the most probable substituent groups present in this substance and shows to the user the selected substituent groups together with their average error range of chemical shifts. The average error range is the average deviation calculated from the chemical shifts of the sample in question and then matched with the chemical shifts values stored in the database. Therefore, the smaller the range, the more reliable the result be will.The database especially elaborated for this program contains 161 substituent groups that are frequently encountered in terpenoid compounds. It is essential that the MACRONO program is the first program to be used in the MONOREG

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