doi:10.1016/S0097-8485(00)00096-6 
Copyright © 2001 Elsevier Science Ltd. All rights reserved.
Characteristic substructures in sets of organic compounds with similar infrared spectra
Plamen N. Pencheva and Kurt Varmuza
, 
, b
a Department of Analytical Chemistry, University of Plovdiv, BG-4000 Plovdiv, Bulgaria
b Laboratory for Chemometrics, Institute of Food Chemistry and Food Technology, Vienna University of Technology, Getreidemarkt 9/160, A-1060 Vienna, Austria
Received 3 April 2000;
accepted 18 August 2000
Available online 13 April 2001.
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Abstract
A method based on the determination of maximum common substructures is applied for the generation of substructures which are characteristic for a given set of molecular structures. The molecular structures are from hitlists obtained by spectral library searches; the hitlists contain those reference compounds, which have infrared spectra most similar to that from the query compound. The influences of various parameters of this method are investigated with the aim to improve the relevance of the obtained substructures for the structure of the query compound.
Author Keywords: Spectral library search; Structure elucidation; Maximum common substructure; Software
Fig. 1. Examples for characteristic substructures found by the MCS approach. (A) compound 4 (highest effectiveness); (B) compound 1 (lowest effectiveness). Compounds are listed in Table 2. Y, substructure is part of the query structure, N, substructure is not part of the query structure; the number given is the frequency (number of hitlist structures containing the substructure). Spectral similarity measure was the correlation coefficient, size of hitlist was 50, factor f for ranking was 0.3.
Fig. 2. Averaged effectiveness, Em, versus number of used hitlist structures, n.
Fig. 3. Averaged effectiveness, Em versus parameter f for ranking the maximum common substructures (Eq. (1)).
Table 1. Parameters for the MCS algorithm
Table 2. Ten compounds used as unknowns; size of molecules is measured by the number of non-hydrogen atoms
Table 3. Effectiveness E (Eq. (2)) of sets containing characteristic substructures for the ten unknowns listed in Table 2 a
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