The IUPAC International Chemical
Identifier
Use of InChI and InChIKey
InChI is useful for communication between databases, merging data
collections developed using different systems and protocols,
maintaining a laboratory chemical inventory, and passing the
“identity” of a substance to a colleague. The program could
also be useful for chemical suppliers, by giving greatly increased
exposure to their catalogs. The scientific and medical community can
use the InChIKey as a universal chemical identifier: InChI can be
freely searched using Internet search engines. The InChIKey will allow
commercial chemical information providers to have a free structure and
number linking system. Millions of InChIs have already been created; at
least 21 databases now incorporate them. The Royal Society of Chemistry
(RSC) uses InChI in Project Prospect,23 the aim of which is to make the
science within RSC journal articles machine-readable through semantic
enrichment, the integration of metadata into text. Text mining is used
to attach structural information (InChI, SMILES and CML) to chemical
names. A list of software developers, database providers, and journal
publishers incorporating InChI in their products is maintained on the
IUPAC website.24
Acknowledgment
I am grateful to the InChI project team, Steve Heller, Alan McNaught,
Igor Pletnev, Steve Stein, and Dmitrii Tchekhovskoi, for their helpful
comments and suggestions, also to Beda Kosata for his advice on the
IUPAC website.
References
1. The IUPAC International Chemical Identifier (InChI). http://www.iupac.org/inchi/ (accessed January 7, 2009).
2. Stein, S. E.; Heller, S. R.; Tchekhovskoi, D. An
Open Standard for Chemical Structure Representation: The IUPAC Chemical
Identifier. In Proceedings of the 2003
International Chemical Information Conference (Nîmes), Infonortics: Tetbury, UK, 2003; pp. 131-143.
3. Kosata, B. A Website Dedicated to the International Chemical Identifier. http://www.inchi.info/ (accessed December 31, 2008).
4. Heller, S. R.; Pletnev I. InChI and the InChIKey
– A Status Report.
http://www.hellers.com/steve/pub-talks/google-1007/frame.htm (accessed
December 31,
2008).
5. Heller, S. R.; Stein, S. IUPAC InChI.
http://www.hellers.com/steve/pub-talks/google1-1106/frame.htm (accessed
December 31, 2008).
6. Heller, S. R.; Stein, S. Video about InChI.
http://video.google.com/videoplay?docid=-6653695245776470969&q=heller+chemical
(accessed December 31, 2008).
7. Coles, S. J.; Day, N. E.; Murray-Rust, P.; Rzepa,
H. S.; Zhang, Y. Enhancement of the Chemical Semantic Web Through the
Use of InChI Identifiers. Org. Biomol.
Chem. 2005, 3(10), 1832-1834.
8. InChI Project Website. http://iupac.org/projects/2000/2000-025-1-800.html (accessed January 7, 2009).
9. InChI can be downloaded from http://iupac.org/inchi/download/index.html (accessed January 7, 2009).
10. Day, N. Unofficial InChI FAQ. http://wwmm.ch.cam.ac.uk/inchifaq/ (accessed December 31, 2008).
11. MDL CTfile formats. http://www.mdl.com/solutions/white_papers/ctfile_formats.jsp (accessed December 31, 2008).
12. IUPAC Project Meetings: Extensible Markup Language (XML)
Data Dictionaries and Chemical Identifier. http://warr.com/inchi.pdf
(accessed December 31, 2008).
13. McKay, B. D. Practical Graph Isomorphism. Congressus Numerantium 1981, 30, 45–87.
14. Morgan, H. L. The Generation of a Unique Machine Description
for Chemical Structures - a Technique Developed at Chemical Abstracts
Service. J. Chem.
Doc. 1965, 5, 107-113.
15. InChI project. http://sourceforge.net/projects/inchi/ (accessed December 31, 2008).
16. InChIKey Overview. http://www.inchi.info/inchikey_overview_en.html (accessed December 31, 2008).
17. Secure Hash Standard. http://csrc.nist.gov/publications/fips/fips180-2/fips180-2withchangenotice.pdf (accessed December 31, 2008).
18. PubChem Server Side Structure Editor. http://pubchem.ncbi.nlm.nih.gov/edit/ (accessed December 31, 2008).
19. ChemSketch. http://www.acdlabs.com/download/chemsk.html (accessed December 31, 2008).
20. ChemSpider InChI services. http://www.chemspider.com/inchi.asmx (accessed December 31, 2008).
21. CAS REGISTRY and CAS Registry Numbers. http://www.cas.org/expertise/cascontent/registry/regsys.html (accessed December 31, 2008).
22. SMILES - A Simplified Chemical Language. http://www.daylight.com/dayhtml/doc/theory/theory.smiles.html (accessed December 31, 2008).
23. RSC Project Prospect http://www.rsc.org/publishing/journals/projectprospect/faq.asp (accessed December 31, 2008).
24. InChI Use by Software Developers, Database Providers, and Journal Publishers. http://old.iupac.org/inchi/adopters.html. (accessed December 31, 2008).
- Dr. Wendy A. Warr, Wendy Warr
& Associates (wendy@warr.com, http://www.warr.com), December 2008
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