Automated Structure Elucidation of Organic Molecules from 13C NMR Spectra Using Genetic Algorithms and Neural Networks

Journal of Chemical Information and Computer Sciences

Volumn 41, Issue 6, 2001, Pages 1535-1546

  Meiler, Jens ^a   Will, Martin ^b  

^a GOETHE UNIVERSITY   (Germany)

^b BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ORGANIC COMPOUND;

ALGORITHM; ARTICLE; ARTIFICIAL NEURAL NETWORK; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALGORITHMS; CARBON ISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NEURAL NETWORKS (COMPUTER); ORGANIC CHEMICALS; SUPPORT, NON-U.S. GOV'T;

GENETIC ALGORITHMS; MOLECULAR STRUCTURE; NEURAL NETWORKS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

CHEMICAL SHIFT;

ORGANIC COMPOUNDS;

EID: 0035498336     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0102970     Document Type: Article

References (31)

1. Benecke, C.; Grund, R.; Hohberger, R.; Kerber, A.; Laue, R.; Wicland, T. MOLGEN+, a generator of connectivity isomers and stereoisomers for molecular structure elucidation. Anal. Chim. Acta 1995, 314, 141-147.
2. Wieland, T.; Kerber, A.; Laue, R. Principles of the Generation of Constitiutional and Configurational Isomers. J. Chem. Inf. Comput. Sci. 1996, 36, 413-419.
3. Lindel, T.; Junker, J.; Köck, M. COCON: From NMR Correlation Data to Molecular Constitution. J. Mol. Model. 1997, 3, 364-368.
4. Köck, M.; Junker, J.; Maier, W.; Will, M.; Lindel, T. A. COCON Analysis of Proton-Poor Heterocycles - Application of Carbon Chemical Shift Predictions for the Evaluation of Structural Proposels. Eur. J. Org. Chem. 1999, 579-586.
5. Meiler, J.; Will, M.; Meusinger, R. Fast Determination of 13C NMR Chemical Shifts Using Artificial Neural Networks. J. Chem. Inf. Comput. Sci. 2000, 40, 1169-1176.
6. Meiler, J.; Köck, M. Structure Elucidation by Automatic Generation and Analysis of Molecule Databases from NMR Connectivity Information Using Substructure Analysis and 13C NMR Chemical Shift Prediction. 2001, submitted for publication.
7. Chemical Concepts: Karlsruhe, 2001.
8. Will, M.; Fachinger, W.; Richert, J. R. Fully Automated Structure Elucidation - A Spectroscopist's Dream Comes True. J. Chem. Inf. Consul. Sci. 1996, 36, 221-227.
9. Zupan, J.; Gasteiger, J. VCH Verlagsgesellschaft mbH: Weinheim, 1993.
10. Kvasnicka, V.; Sklenak, S.; Pospichal, J. Application of Recurrent Neural Network in Chemistry. Prediction and Classification of 13C NMR Chemical Shiftsin a Series of Monosubstituted Benzenes. J. Chem. Inf. Comput. Sci. 1992, 32, 742-747.
11. Doucet, J.-P.; Panaye, A.; Feuilleaubois, E.; Ladd, P. Neural networks and carbon-13 NMR shift prediction. J. Chem. Inf. Comput. Sci. 1993, 33, 320-324.
12. Panaye, A.; Doucet, J.-P.; Fan, B. T.; Feuilleaubois, E.; Azzouzi, S. R. E. Artificial neural network simulation of 13C NMR shifts for methyl-substituted cyclohexanes. Chemom. Intell. Lab. Syst. 1994, 24, 129-135.
13. Sklenak, S.; Kvasnicka, V.; Pospichal, J. Prediction of 13C NMR chemical shifts by neural networks in a series of monosubstituted benzenes. Chem. Pap. 1994, 48, 135-140.
14. Clouser, D. L.; Jurs, P. C. Simulation of the 13C nuclear magnetic resonance spectra of trisaccharides using multiple linear regression analysis and neural networks. Carbohydr. Res. 1995, 271, 65-77.
15. Svozil, D.; Pospichal, J.; Kvasnicka, V. Neural Network Prediction of Carbon-13 NMR Chemical Shifts of Alkanes. J. Chem. Inf. Comput. Sci. 1995, 35, 924-928.
16. Thomas, S.; Kleinpeter, H. Assignment of the 13C NMR chemical shifts of substituted naphthalenes from charge density with an artificial neural network. J. Prakt. Chem./Chem.-Ztg. 1995, 337, 504-507.
17. Clouser, D. L.; Jurs, P. C. Simulation of the 13C Nuclear Magnetic Resonance Spectra of Ribonucleosides Using Multiple Linear Regression Analysis and Neural Networks. J. Chem. Inf. Comput. Sci. 1996, 36, 168-172.
18. Ivanciuc, O.; Rabine, J. P.; Cabrol-Bass, D.; Panaye, A.; Doucet, J.P. 13C NMR Chemical Shift Prediction of sp2 Carbon Atoms in Acyclic Alkenes Using Neural Networks. J. Chem. Inf. Comput. Sci. 1996, 36, 644-653.
19. Meiler, J.; Meusinger, R.; Will, M. Neural Network Prediction of 13C NMR Chemical Shifts of Substituted Benzenes. Monatsh. Chem. 1999, 130. 1089-1095.
20. Pearlman, D. A. Automated detection of problem restraints in NMR data sets using the FINGAR genetic algorithm method. J. Biomol. NMR 1999, 13, 325-335.
21. Fisher, B.; Dillon, N.; Carpenter, T.; Hall, L. Design by Genetic Algorithm of a Z Gradient Set for Magnetic Resonance Imagine of the Human Brain. Measurement Sci. Technol. 1995, 6, 904-909.
22. Meusinger, R.; Moros, R. In Software - Entwicklung in der Chemie; Gasteiger, J., Ed.; Gesellschaft Deutscher Chemiker: Frankfurt am Main, 1995; Vol. 10, pp 209-216.
23. Pearlman, D. A. FINGAR: A newgenetic algorithm-based method for fitting NMR data. J. Biomol. NMR 1996, 8, 49-66.
24. Li, L.; Durden, T. A.; Freeman, S. J.; Furie, B. C.; Furie, B.; Baleja, J. D.; Smith, H.; Hiskey, R. G.; Pedersen, L. G. Refinement of the NMR Solution Structure of the γ-Carboxyglutamic Acid Domain of Coagulation Factor IX Using Molecular Dynamics Simulation with Initial Ca2+ Positions Determined by a Genetic Algorithm. Biochemistry 1997, 36, 2132-2138.
25. Choy, W. Y.; Sanctuary, B. C. Using Genetic Algorithms with a Priori Knowledge for Quantitative NMR Signal Analysis. J. Chem. Inf. Comput. Sci. 1998, 38, 685-690.
26. Robien, W. Das CSEARCH-NMR-Datenbanksystem. Nachr. Chem. Technol. Lab. 1998, 46, 74-77.
27. Clerc, J.-T.; Sommerauer, H. A Minicomputer Program Based On Additivity Rules For The Estimation Of 13C NMR Chemical Shifts. Anal. Chim. Acta 1977, 95, 33-40.
28. Ebraheem, K. A. K.; Webb, G. A. Semiempirical Calculations of the Chemical Shifts of Nuclei other than Protons. Prog. NMR Spectrosc. 1977, 11, 149-181.
29. Bremser, W.; Ernst, L.; Franke, B.; Gerhards, R.; Hardt, A. Verlag Chemie: Weinheim, 1981.
30. Fürst, A.; Pretsen, E. A computer program for the prediction of 13C NMR chemical shifts of organic compounds. Anal. Chim. Acta 1990, 229, 17-25.
31. Meiler, J. www.jens-meiler.de, 2001.