Biochemical ontologies aim to capture and represent biochemical entities and the relations that exist between them in an accurate and precise manner. A fundamental starting point is the use of identifiers that precisely and uniquely identify some biochemical entity, whether it be a substance, a quality or some biological process. Yet, our current approach for generating identifiers doing so is often haphazard and incomplete. This prevents us from accurately integrating knowledge and also leads to under specification of our knowledge. This talk aims to initiate a discussion on plausible structure-based strategies for biochemical identity, ultimately to generate identifiers in an automatic and curator/database independent fashion, whether it be at molecular level or some part thereof (e.g. residues, collection of residues, atoms, collection of atoms, functional groups). With structure-based identifiers in hand, we will be in a position to accurately capture specific biochemical knowledge, such as how a set of residues in a binding site are involved in a chemical reaction including the fact that a key nitrogen atom must first be de-protonated. Thus, this will enhance our current representation of biochemical knowledge and make it fundamentally more useful.

1. Accurate biochemical knowledge starting with precise structure-based criteria for molecular identity Michel Dumontier , Ph.D. Assistant Professor of Bioinformatics Department of Biology, School of Computer Science Institute of Biochemistry, Ottawa Institute of Systems Biology Carleton University 01/04/2009 NCBO Seminar Series::Michel Dumontier

3. Bio2RDF: 2.3B triples of SPARQL-accessible linked biological data! Chemical Parts!

9. (S)-Glutamic Acid InChI= {version}1 /{formula}C5H9NO4 /c{connections}6-3(5(9)10)1-2-4(7)8 /h{H_atoms}3H,1-2,6H2,(H,7,8)(H,9,10) /p{protons}+1 /t{stereo:sp3}3- /m{stereo:sp3:inverted}0 /s{stereo:type (1=abs, 2=rel, 3=rac)}1 /i{isotopic:atoms}4+1 01/04/2009 NCBO Seminar Series::Michel Dumontier

10. More non-core info captured in “AuxInfo” string... AuxInfo= {version}1 /{normalization_type}1 /N:{original_atom_numbers}5,6,2,7,1,4,8,9,10,11 /E:{atom_equivalence}(7,8)(9,10) /it:{abs_stereo_inverted:sp3}im /I:{isotopic:original_atom_numbers} /E:{isotopic:atom_equivalence}m /rA:{reversibility:atoms}11nCCHN+CCC.i13OOOO /rB:{reversibility:bonds}s1;N2;P2;s2;s5;s6;s7;d7;d1;s1; /rC:{reversibility:xyz}6.1671,-19.3365,0;7.0125,-18.4864,0;6.4113,-17.4485,0;7.6089,-17.4485,0;7.8578,-19.3318,0;8.891,-18.7306,0;9.7363,-19.576,0;9.7316,-20.7735,0;10.8916,-19.266,0;5.0071,-19.0265,0;6.1624,-20.534,0; AuxInfo=1/1/N:5,6,2,7,1,4,8,9,10,11/E:(7,8)(9,10)/it:im/I:/E:m/rA:11nCCHN+CCC.i13OOOO/rB:s1;N2;P2;s2;s5;s6;s7;d7;d1;s1;/rC:6.1671,-19.3365,0;7.0125,-18.4864,0;6.4113,-17.4485,0;7.6089,-17.4485,0;7.8578,-19.3318,0;8.891,-18.7306,0;9.7363,-19.576,0;9.7316,-20.7735,0;10.8916,-19.266,0;5.0071,-19.0265,0;6.1624,-20.534,0; 01/04/2009 NCBO Seminar Series::Michel Dumontier

13. OpenBabel CML SDF O1[C@@H]([C@@H](O)([C@H](O)([C@@H](O)([C@@H]1(O)))))(CO) 79025 IUPAC InChI=1/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1 InCHI α -D-Glucose 6-(hydroxymethyl)oxane-2,3,4,5-tetrol OR (2R,3R,4S,5R,6R)-6 -(hydroxymethyl)tetrahydro -2H-pyran-2,3,4,5-tetraol SMILES

15. Chemical Ontology Chemical Knowledge for the Semantic Web. Mykola Konyk , Alexander De Leon , and Michel Dumontier . LNBI . 2008. 5109:169-176. Data Integration in the Life Sciences (DILS2008) . Evry. France.

16. http://code.google.com/p/semanticwebopenbabel/ 01/04/2009 NCBO Seminar Series::Michel Dumontier

17. Describing chemical functional groups in OWL-DL for the classification of chemical compounds hydroxyl group methyl group Knowledge of functional groups is important in chemical synthesis, pharmaceutical design and lead optimization. Functional groups describe chemical reactivity in terms of atoms and their connectivity, and exhibits characteristic chemical behavior when present in a compound. N Villanueva-Rosales, MDumontier. 2007. OWLED, Innsbruck, Austria. Ethanol 01/04/2009 NCBO Seminar Series::Michel Dumontier

19. Fully Classified Ontology 35 FG 01/04/2009 NCBO Seminar Series::Michel Dumontier

21. Organic Compound Ontology 28 OC 01/04/2009 NCBO Seminar Series::Michel Dumontier

28. PSI-MOD contains modified residues with links to structural descriptions 01/04/2009 NCBO Seminar Series::Michel Dumontier

32. 01/04/2009 NCBO Seminar Series::Michel Dumontier

37. dumontierlab.com [email_address] Special thanks to PhD Student Leonid Chepelev for insightful discussions  semanticscience.org 01/04/2009 NCBO Seminar Series::Michel Dumontier