InChI Tag: Reactions

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A possible extension to the RInChI as a means of providing machine readable process data

Content type Publication Reactions

A possible extension to the RInChI as a means of providing machine readable process data

Philipp-Maximilian Jacob, Tian Lan, Jonathan M. Goodman & Alexei A. Lapkin
Journal of Cheminformatics volume 9, Article number: 23 (2017)

Abstract: The algorithmic, large-scale use and analysis of reaction databases such as Reaxys is currently hindered by the absence of widely adopted standards for publishing reaction data in machine readable formats. Crucial data such as yields of all products or stoichiometry are frequently not explicitly stated in the published papers and, hence, not reported in the database entry for those reactions, limiting their usefulness for algorithmic analysis. This paper presents a possible extension to the IUPAC RInChI standard via an auxiliary layer, termed ProcAuxInfo, which is a standardised, extensible form in which to report certain key reaction parameters such as declaration of all products and reactants as well as auxiliaries known in the reaction, reaction stoichiometry, amounts of substances used, conversion, yield and operating conditions. The standard is demonstrated via creation of the RInChI including the ProcAuxInfo layer based on three published reactions and demonstrates accurate data recoverability via reverse translation of the created strings. Implementation of this or another method of reporting process data by the publishing community would ensure that databases, such as Reaxys, would be able to abstract crucial data for big data analysis of their contents.

Analysing a billion reactions with the RInChI

Content type Publication Reactions

Analysing a billion reactions with the RInChI

Jonathan M. Goodman, Gerd Blanke and Hans Kraut
From the journal Pure and Applied Chemistry

Abstract: The RInChI is a canonical identifier for reactions which is widely used in reaction databases. It can be used to handle large collections of reactions and to link information from diverse data sources. How much information can it handle? Studies of the SAVI database, which contains more than a billion reactions, demonstrate that the RInChI is useful in analysing such a large collection of molecular data, and the reduced form of the Web-RInChIKey contains enough information to be an effective differentiator of reactions. Issues of NH tautomerism and stereochemistry are handled effectively. The RInChI illustrates that some of the properties of the algorithmically-generated SAVI database differ from SPRESI, which is a collection of experimental data. The RInChI has different properties to Reaction SMILES and both approaches provide useful and distinct information. We recommend that the RInChI be included in data models for reactions.

International chemical identifier for reactions (RInChI)

Content type Publication Reactions

International chemical identifier for reactions (RInChI)

Guenter Grethe, Jonathan M Goodman & Chad HG Allen
Journal of Cheminformatics volume 5, Article number: 45 (2013)

Abstract: The IUPAC International Chemical Identifier (InChI) provides a method to generate a unique text descriptor of molecular structures. Building on this work, we report a process to generate a unique text descriptor for reactions, RInChI. By carefully selecting the information that is included and by ordering the data carefully, different scientists studying the same reaction should produce the same RInChI. If differences arise, these are most likely the minor layers of the InChI, and so may be readily handled. RInChI provides a concise description of the key data in a chemical reaction, and will help enable the rapid searching and analysis of reaction databases.

International chemical identifier for reactions (RInChI)

Cheminformatics Classroom Material Content type Reactions

International chemical identifier for reactions (RInChI)

Guenter Grethe, Gerd Blanke, Hans Kraut & Jonathan M. Goodman
Journal of Cheminformatics volume 10, Article number: 22 (2018)
May 9, 2018

Abstract: The Reaction InChI (RInChI) extends the idea of the InChI, which provides a unique descriptor of molecular structures, towards reactions. Prototype versions of the RInChI have been available since 2011. The first official release (RInChI-V1.00), funded by the InChI Trust, is now available for download (http://www.inchi-trust.org/downloads/). This release defines the format and generates hashed representations (RInChIKeys) suitable for database and web operations. The RInChI provides a concise description of the key data in chemical processes, and facilitates the manipulation and analysis of reaction data.