Croatica Chemica Acta, Vol. 79 No. 3, 2006.
Original scientific paper
CASE via MS: Ranking Structure Candidates by Mass Spectra
Adalbert Kerber
Markus Meringer
Christoph Rücker
Abstract
Two important tasks in computer-aided structure elucidation (CASE) are the generation of candidate structures from a given molecular formula, and the ranking of structure candidates according to compatibility with an experimental spectrum. Candidate ranking with respect to electron impact mass spectra is based on virtual fragmentation of a candidate structure and comparison of the fragments’ isotope distributions against the spectrum of the unknown compound, whence a structure–spectrum compatibility matchvalue is computed. Of special interest is the matchvalue’s ability to distinguish between the correct and false constitutional isomers. Therefore a quality score was computed in the following way: For a (randomly selected) spectrum–structure pair from the NIST MS library all constitutional isomers are generated using the structure generator MOLGEN. For each isomer the matchvalue with respect to the library spectrum is calculated, and isomers are ranked according to their matchvalues. The quality of the ranking can be quantified in terms of the correct structure’s relative ranking position (RRP). This procedure was repeated for 100 randomly selected spectrum–structure pairs belonging to small organic compounds. In this first approach the RRP of the correct isomer was 0.27 on average.
Keywords
computer-aided structure elucidation; electron impact mass spectrometry; spectrum–structure compatibility matchvalue; constitutional isomers; structure generation
Hrčak ID:
5653
URI
Publication date:
12.11.2006.
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