Presentation on theme: "Reactor latest ChemAxon User Group MeetingBudapest 2007 György Pirok."— Presentation transcript:
Reactor latest ChemAxon User Group MeetingBudapest 2007 György Pirok
Content Elements of the Virtual Synthesis Encoding Synthetic Knowledge in Reactions Applications New Features Summary
Elements of the Virtual Synthesis Technology A language for describing chemical rules –Chemical Terms A library of selective reactions knowing chemistry –Chemaxon Reaction Library A reaction engine with high capacity and performance –Reactor Virtual reaction applications –Reactor GUI, Metabolizer
Encoding Synthetic Knowledge in Reactions The Baeyer-Villiger oxidation: generic scheme The Baeyer-Villiger oxidation is an organic reaction in which a ketone or aldehyde is oxidized to an ester by treatment with peroxy acids or hydrogen peroxide. The stereo configuration remains intact during the reactions. Retretention L[H,C]carbon or hydrogen
Encoding Synthetic Knowledge in Reactions The Baeyer-Villiger oxidation: excluding compounds giving side reactions, destroying the catalyst EXCLUDE: match(reactant(0), "[H][#5,#14,#15,#16]") || match(reactant(0), "C=S") || match(reactant(0), "[H]OC=O") || match(reactant(0), "[O-]C=O") Exclude reagents containing BH, SiH, PH, SH or thiocarbonyl or carboxyl and carboxylate groups.
Encoding Synthetic Knowledge in Reactions The Baeyer-Villiger oxidation: finding reactive sites REACTIVITY: !match(ratom(2), "[H][C:1](C=O)C=O", 1) Beta diketones are able to enolize, they do not react on the carbon between the two carbonyl groups.
Encoding Synthetic Knowledge in Reactions The Baeyer-Villiger oxidation: finding the most reactive sites SELECTIVITY: -charge(ratom(2), "sigma") The oxygen goes between the carbonyl carbon and its neighbour having the lowest sigma charge value. δδ
Encoding Synthetic Knowledge in Reactions The Baeyer-Villiger oxidation as a selective reaction REACTIVITY: !match(ratom(2), "[H][C:1](C=O)C=O", 1) SELECTIVITY: -charge(ratom(2), "sigma") EXCLUDE: match(reactant(0), "[H][#5,#14,#15,#16]") || match(reactant(0), "C=S") || match(reactant(0), "[H]OC=O") || match(reactant(0), "[O-]C=O")
The Reaction Editor Built in Reaction Library Editor
The Reaction Editor Chemical Terms Editor for Rule Design
The Reaction Editor Internal Example and Property Editors
The Reaction Editor Built-in Reactant Standardizer and Reaction Tester
What's new in Reactor Automapping reaction results Aromaticity is automatically detected (no standardization needed) Synthesis code generation for the products Bromination(Acylation(AMINE12, ACID37):1):2 New and enhanced reactions in the library Separate example reaction properties Reaction testing with the internal examples Rule Editor Automatic reactant standardization can be built-in the virtual reaction Product standardization is a runtime option The Reactor license will contain about 10 sample reactions The new reaction library and reaction capabilities in Cartridge will be included in the Reactor Pro license
Future Features Reactor module in Instant JChem working in database tables (new, simplifed interface) Processing multistep reactions Transition states and intermedier based calculations Simplified rules –simplified Chemical Terms language –new plugin functions for reactivity and selectivity predictions –named functional groups (SMARTS-less rules) Reaction library can be classified by several aspects Functional group name based reaction definition amine>>amide
Summary What is Reactor? –Reactor is an effective and selective virtual synthesis tool transforming molecules to products according to given reaction schemes. What is it good for? –combichem library enumeration –reaction prediction –other transformation based applications (xenobiotic biotransformation, bacterial biodegradation, random synthesis, generating chlick chemistry universe, etc.) How can I use it? –Off the shelf (Reactor Application) –Integrate into applications (Java/.NET API, Oracle Cartridge) –Reaction Library option with predefined synthetic reactions –FREE for Academics
Acknowledgements Nóra Máté, Zsolt Mohácsi Plugin system, Chemical Terms Evaluator, Reactor Jenő Varga, Erzsébet Czinege Reaction Library, Reactor József Szegezdi, Ferenc Csizmadia Property predictions, calculations István Cseh, Attila Szabó Reactor Application, Chemical Terms Editor Szilárd Dóránt, Szabolcs Csepregi Substructure searching functions, Pipeline Pilot integration Péter Kovács JChem Cartridge integration Miklós Vargyas Chemical Terms Evaluator
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