Evaluation of CADASTER QSAR models for the aquatic toxicity of (benzo)triazoles and prioritisation by consensus prediction

ATLA Alternatives to Laboratory Animals

Volumn 41, Issue 1, 2013, Pages 49-64

  Cassani, Stefano ^a   Kovarich, Simona ^a   Papa, Ester ^a   Roy, Partha Pratim ^a   Rahmberg, Magnus ^b   Nilsson, Sara ^b   Sahlin, Ullrika ^c   Jeliazkova, Nina ^d   Kochev, Nikolay ^e   Pukalov, Ognyan ^e   Tetko, Igor V ^f   Brandmaier, Stefan ^f   Durjava, Mojca Kos ^g   Kolar, Boris ^g   Peijnenburg, Willie ^h,i   Gramatica, Paola ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b IVL SWEDISH ENVIRONMENTAL RESEARCH INSTITUTE   (Sweden)

^c LINNAEUS UNIVERSITY   (Sweden)

^d IDEACONSULT LTD   (Bulgaria)

^e UNIVERSITY OF PLOVDIV   (Bulgaria)

^f INSTITUTE OF EPIDEMIOLOGY   (Germany)

^g Institute of Public Health Maribor   (Slovenia)

^h NATIONAL INSTITUTE FOR PUBLIC HEALTH AND THE ENVIRONMENT   (Netherlands)

ⁱ LEIDEN UNIVERSITY   (Netherlands)

Author keywords

(Benzo)triazoles; Applicability domain; Aquatic toxicity; Consensus; QSAR; REACH; Validation

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; TRIAZOLE;

AQUATIC SPECIES; ARTICLE; DAPHNIA MAGNA; FISH; NONHUMAN; ONCHORHYNCHUS MYKISS; PRIORITY JOURNAL; PSEUDOKIRCHNERIELLA SUBCAPITATA; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL ANALYSIS; TOXICITY;

EID: 84877117871     PISSN: 02611929     EISSN: None     Source Type: Journal    
DOI: 10.1177/026119291304100107     Document Type: Article

References (36)

1. Anon.(undated).CAse studies on the Development and Application of in-Silico Techniques for Environmental hazard and Risk assessment.Available at: www.cadaster.eu (Accessed 16.11.12).
2. European Parliament (2006).Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration Evaluation Authorisation and Restriction of Chemicals (REACH) establishing a European Chemicals Agency amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC 93/67/EEC 93/105/EC and 2000/21/EC.Official Journal of the European Union L396 30.12.2006 1-849.
3. Wolschke H.Xie Z.Moller A.Sturm R.Ebinghaus R.(2011).Occurrence distribution and fluxes of benzotriazoles along the German large river basins into the North Sea.Water Research 45 6259-6266.
4. Cancilla D.Martinez J.Van Aggelen G.(1998) Detection of aircraft deicing/antiicing fluid additives in a perched water monitoring well at an international airport.Environmental Science Tech nology 32 3834-3835.
5. OECD (2004).OECD Principles for the Validation for Regulatory Purposes of (Quantitative) Structure-Activity Relationship Models 2pp.Paris France: 37th Joint Meeting of the Chemicals Committee and Working Party on Chemicals Pesticides and Biotechnology.Available at: http://www.oecd.org/dataoecd/33/37/ 37849783.pdf (Accessed 16.11.12).
6. Bhhatarai B.Gramatica P.(2011).Modelling physico-chemical properties of (benzo)triazoles and screening for environmental partitioning.Water Research 45 1463-1471.
7. Gramatica P.Cassani S.Roy P.P.Kovarich S.Yap C.W.Papa E.(2012).QSAR modelling is not "push a button and find a correlation": A case study of toxicity of (benzo-)triazoles on algae.Molecular Informatics 11-12 817-835.
8. OECD (undated).OECD Cooperative Chemicals Assessment Programme.Available at: http://www.oecd.org/chemicalsafety/assessmentofchemicals/oecd cooperativechemicalsassessmentprogramme.htm (Accessed 16.11.12).
9. Todeschini R.Consonni V.Mauri A.Pavan M.(undated).DRAGON Software.Milan Italy: Talete srl.Available at: www.talete.mi.it (Accessed 17.12.12).
10. Yap C.W.(2011).PaDEL-Descriptor: An open source software to calculate molecular descriptors and fingerprints.Journal of Computational Chemistry 32 1466-1474.
11. CADASTER (undated).QSPR-THESAURUS Online Platform.Available at: http://qspr-thesaurus.eu/login/show.do?render-mode=full (Accessed 16.11.12).
12. University of Hertfordshire (2011).The PPDB Pesticide Properties Database.Available at: http://sitem.herts.ac.uk/aeru/footprint/index2.htm (Accessed 16.11.12).
13. Durjava M.Kolar B.Arnus L.Papa E.Kovarich S.Sahlin U.Peijnenburg W.(2013).Experimental assessment of the environmental fate and effects of triazoles and benzotriazole.ATLA 41 65-75.
14. Zhu H.Tropsha A.Fourches D.Varnek A.Papa E.Gramatica P.Oberg T.Dao P.Cherkasov A.Tetko I.V.(2008).Combinational QSAR modeling of chemical toxicants tested against Tetrahymena pyriformis.Journal of Chemical Information Modeling 48 766-784.
15. Gramatica P.Pilutti P.Papa E.(2004).Validated QSAR prediction of OH tropospheric degradability: Splitting into training-test set and consensus modeling.Journal of Chemical Information Computer Science 44 1794-1802.
16. OECD (2011).OECD Guidelines for Testing of Chemicals No.201: Freshwater Alga and Cyanobacteria Growth Inhibition Test 25 pp.Paris France: Organisation for Economic Co-operation and Development.Available at: http://www.oecd- ilibrary.org/environment/test-no-201-alga-growth-inhibitiontest-9789264069923- en (Accessed 26.02.13)
17. OECD (2004).OECD Guidelines for the Testing of Chemicals No.202: Daphnia sp.Acute Immobilisation Test 12pp.Paris France: Organisation for Economic Co-operation and Development.Available at: http://www.oecd-ilibrary.org/ environment/test-no-202-daphnia-sp-acute-immobilisation-test-9789 264069947-en (Accessed 16.12.12).
18. European Commission (1991).Directive 67/548/EEC (Annex VI).General Classification and Labelling Requirements for Dangerous Substances and Preparations.Official Journal of the European Union L180 09.07.1991 1-79.
19. Chirico N.Papa E.Kovarich S.Cassani S.Gramatica P.(2012).QSARINS: Software for QSAR MLR Model Development and Validation 8pp.Varese Italy: University of Insubria.Available at: http://dipbsf.uninsubria.it/qsar/news/ QSARINS-swGram.pdf (Accessed 15.12.12).
20. Gramatica P.(2007).Principles of QSAR models validation: Internal and external.QSAR Combinatorial Science 26 694-701.
21. Gasteiger J.Zupan J.(1993).Neural networks in chemistry.Angewandte Chemie International Edition in English 32 503-527.
22. Shi M.Fang H.Tong W.Wu J.Perkins R.Blair R.M.Branham W.S.Dial S.L.Moland C.L.Sheehan D.M.(2001).QSAR models using a large diverse set of estrogens.Journal of Chemical Information Computer Sciences 41 186-195.
23. Schuurmann G.Ebert R.U.Chen J.Wang B.Kuhne R.(2008).External validation and prediction employing the predictive squared correlation coefficient test set activity mean vs training set activity mean.Journal of Chemical Information Modeling 48 2140-2145.
24. Consonni V.Ballabio D.Todeschini R.(2010).Evaluation of model predictive ability by external validation techniques.Journal of Chemometrics 24 194-201.
25. Chirico N.Gramatica P.(2011).Real external predictivity of QSAR models: How to evaluate it?Comparison of different validation criteria and proposal of using the concordance correlation coefficient.Journal of Chemical Information Modeling 51 2320-2335.
26. Chirico N.Gramatica P.(2012).Real external predictivity of QSAR models.Part 2.New intercomparable thresholds for different validation criteria and the need for scatter plot inspection.Journal of Chemical Information Modeling 52 2044-2058.
27. Anon.(undated).SIMCA.Umeå Sweden: Umetrics.Available at: http://www.umetrics.com/simca (Accessed 16.11.12).
28. Development Core Team (2008).R: A Language and Environment for Statistical Computing.Vienna Austria: R Foundation for Statistical Computing.29.Helmholtz-Zentrum Munchen eADMET GmbH (undated).Online Chemical Modeling Environment Project (OCHEM).Available at: http://ochem.eu (Accessed 16.12.12).
29. Gasteiger J.(2006).Of molecules and humans.Journal of Medicinal Chemistry 49 6429-6434.
30. Sushko I.Novotarskyi S.Korner R.Pandey A.K.Rupp M.Teetz W.Brandmaier S.Abdelaziz A.Prokopenko V.V.Tanchuk V.Y.Todeschini R.Var nek A.Marcou G.Ertl P.Potemkin V.Grishina M.Gasteiger J.Schwab C.Baskin I.I.Palyulin V.A.Radchenko E.V.Welsh W.J.Kholodovych V.Chekmarev D.Cherkasov A.Aires-de-Sousa J.Zhang Q.Y.Bender A.Nigsch F.Patiny L.Williams A.Tkachenko V.Tetko I.V.(2011).Online chemical modeling environment (OCHEM): Web platform for data storage model development and publishing of chemical information.Journal of Computer-aided Molecular Design 25 533-554.
31. Breiman L.(2001).Random forests.Machine Learning 45 5-32.
32. Tetko I.V.(2008).Associative neural network.Methods in Molecular Biology 458 185-202.
33. Sushko I.Novotarskyi S.Korner R.Pandey A.K.Cherkasov A.Li J.Gramatica P.Hansen K.Schroeter T.Muller K.R.Xi L.Liu H.Yao X.Oberg T.Hormozdiari F.Dao P.Sahinalp C.Todeschini R.Polishchuk P.Artemenko A.Kuz'min V.Martin T.M.Young D.M.Fourches D.Muratov E.Tropsha A.Baskin I.Horvath D.Marcou G.Muller C.Varnek A.Prokopenko V.V.Tetko I.V.(2010).Applicability domains for classification problems: Benchmarking of distance to models for Ames mutagenicity set.Journal of Chemical Information Modeling 50 2094-2111.
34. Todeschini R.Ballabio D.Consonni V.Mauri A.Pavan M.(2004).MobyDigs 1.0.Milan Italy: Talete srl.Available at: www.talete.mi.it (Accessed 17.12.12).
35. Jackson J.E.(1991).A User's Guide to Principal Components 592 pp.New York NY USA: Wiley.37.Anon.(1995).SCAN: Software for Chemometric Analy sis ver.1.1 for Windows.State College PA USA: Minitab Inc.
36. US EPA (2012).Standalone Version 1.11 of ECOSAR.Washington DC USA: US Environmen tal Protection Agency.Available at: http://www.epa.gov/oppt/newchems/ tools/21ecosar.htm (Accessed 16.12.12).