International Chemical Identifier

Developer(s)InChI Trust
Initial releaseApril 15, 2005 (2005-04-15)[1][2]
Stable release
1.06 / December 15, 2020 (2020-12-15)
Operating systemMicrosoft Windows and Unix-like
PlatformIA-32 and x86-64
Available inEnglish
LicenseIUPAC / InChI Trust Licence

The International Chemical Identifier (InChI, pronounced /ˈɪn/ IN-chee)[3] is a textual identifier for chemical substances, designed to provide a standard way to encode molecular information and to facilitate the search for such information in databases and on the web. Initially developed by the International Union of Pure and Applied Chemistry (IUPAC) and National Institute of Standards and Technology (NIST) from 2000 to 2005, the format and algorithms are non-proprietary. Since May 2009, it has been developed by the InChI Trust, a nonprofit charity from the United Kingdom which works to implement and promote the use of InChI.[4]

The identifiers describe chemical substances in terms of layers of information — the atoms and their bond connectivity, tautomeric information, isotope information, stereochemistry, and electronic charge information.[5] Not all layers have to be provided; for instance, the tautomer layer can be omitted if that type of information is not relevant to the particular application. The InChI algorithm converts input structural information into a unique InChI identifier in a three-step process: normalization (to remove redundant information), canonicalization (to generate a unique number label for each atom), and serialization (to give a string of characters).

InChIs differ from the widely used CAS registry numbers in three respects: firstly, they are freely usable and non-proprietary; secondly, they can be computed from structural information and do not have to be assigned by some organization; and thirdly, most of the information in an InChI is human readable (with practice). InChIs can thus be seen as akin to a general and extremely formalized version of IUPAC names. They can express more information than the simpler SMILES notation and, in contrast to SMILES strings, every structure has a unique InChI string, which is important in database applications. Information about the 3-dimensional coordinates of atoms is not represented in InChI; for this purpose a format such as PDB can be used.

The InChIKey, sometimes referred to as a hashed InChI, is a fixed length (27 character) condensed digital representation of the InChI that is not human-understandable. The InChIKey specification was released in September 2007 in order to facilitate web searches for chemical compounds, since these were problematic with the full-length InChI.[6] Unlike the InChI, the InChIKey is not unique: though collisions are expected to be extremely rare, there are known collisions.[7]

In January 2009 the 1.02 version of the InChI software was released. This provided a means to generate so called standard InChI, which does not allow for user selectable options in dealing with the stereochemistry and tautomeric layers of the InChI string. The standard InChIKey is then the hashed version of the standard InChI string. The standard InChI will simplify comparison of InChI strings and keys generated by different groups, and subsequently accessed via diverse sources such as databases and web resources.

The continuing development of the standard has been supported since 2010 by the not-for-profit InChI Trust, of which IUPAC is a member. The current software version is 1.06 and was released in December 2020.[8] Prior to 1.04, the software was freely available under the open-source LGPL license,[9] but it now uses a custom license called IUPAC-InChI Trust License.[10]

  1. ^ "IUPAC International Chemical Identifier Project Page". IUPAC. Archived from the original on 27 May 2012. Retrieved 2012-12-05.
  2. ^ Heller, S.; McNaught, A.; Stein, S.; Tchekhovskoi, D.; Pletnev, I. (2013). "InChI - the worldwide chemical structure identifier standard". Journal of Cheminformatics. 5 (1): 7. doi:10.1186/1758-2946-5-7. PMC 3599061. PMID 23343401.
  3. ^ "What on Earth is InChI?". IUPAC 100. Retrieved 10 May 2024.
  4. ^ "The InChI Trust and IUPAC". InChI Trust. Retrieved August 22, 2022.
  5. ^ Heller, S.R.; McNaught, A.; Pletnev, I.; Stein, S.; Tchekhovskoi, D. (2015). "InChI, the IUPAC International Chemical Identifier". Journal of Cheminformatics. 7: 23. doi:10.1186/s13321-015-0068-4. PMC 4486400. PMID 26136848.
  6. ^ "The IUPAC International Chemical Identifier (InChI)". IUPAC. 5 September 2007. Archived from the original on October 30, 2007. Retrieved 2007-09-18.
  7. ^ E.L. Willighagen (17 September 2011). "InChIKey collision: the DIY copy/pastables". Retrieved 2012-11-06.
  8. ^ Goodman, Jonathan M.; Pletnev, Igor; Thiessen, Paul; Bolton, Evan; Heller, Stephen R. (December 2021). "InChI version 1.06: now more than 99.99% reliable". Journal of Cheminformatics. 13 (1): 40. doi:10.1186/s13321-021-00517-z. PMC 8147039. PMID 34030732.
  9. ^ McNaught, Alan (2006). "The IUPAC International Chemical Identifier:InChl". Chemistry International. Vol. 28, no. 6. IUPAC. Retrieved 2007-09-18.
  10. ^ "IUPAC/InChI-Trust Licence for the International Chemical Identifier (InChI) Software" (PDF). IUPAC/InChI-Trust. 2020. Retrieved 2022-08-09.

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