InChI - the worldwide chemical structure identifier standard

By Stephen R. Heller, Alan McNaught, Stephen Stein, Dmitrii V. Tchekhovskoi, Igor V. Pletnev. 2013

440 citations recorded by the source corpus.

Since its public introduction in 2005 the IUPAC InChI chemical structure identifier standard has become the international, worldwide standard for defined chemical structures. This article will describe the extensive use and dissemination of the InChI and InChIKey structure representations by and for the world-wide chemistry community, the chemical information community, and major publishers and disseminators of chemical and related scientific offerings in manuscripts and databases.

Subfields: Computational Theory and Mathematics, Organic Chemistry, Physical and Theoretical Chemistry

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In Organic Chemistry

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Citations in the corpus

Automatic Chemical Design Using a Data-Driven Continuous Representation of Molecules (2016, neutral): “The kernel density estimate shows the distribution of data points along each dimension of the latent space.”
PubChem Substance and Compound databases (2015, background): “PubChemRDF enhances cross-integration by providing direct links to available authorative RDF-based resources within applicable subdomains, including reference, synonym and InChIKey (17,18) to MeSH RDF (http://id.nlm.nih.gov/mesh/); protein to UniProt RDF (https://www.ebi.ac.uk/rdf/services/uniprot/)”
Ambiguity of non-systematic chemical identifiers within and between small-molecule databases (2015, neutral): “Among the systematic identifiers are IUPAC names [14], SMILES [15], and International Chemical Identifiers (InChIs) [16, 17].”
PubChemRDF: towards the semantic annotation of PubChem compound and substance databases (2015, background): “D coordinates [4], physical properties (e.g., molecular weight, XLogP3 [5]), and descriptors (e.g., InChI [6], SMILES [7, 8], IUPAC names [9]), as-is possible.”
The RCSB Protein Data Bank: views of structural biology for basic and applied research and education (2014, methodology): “First, we map drugs to PDB ligands by comparing the standard InChI key (38), a unique linear string representation of a molecule, for PDB ligands to drug molecules in DrugBank.”
Geometric deep learning on molecular representations (2021, background): “Some of the most popular stringbased representations are the Wiswesser Line Notation [117], the Sybyl line notation [118], the International Chemical Identifier (InChI) [119], Hierarchical Editing Language for Macromolecules [120], and the Simplified Molecular Input Line Entry System (SMILES) [20].”
CFM-ID: a web server for annotation, spectrum prediction and metabolite identification from tandem mass spectra (2014, background): “The input chemical structure can be provided in SMILES (10) or InChI format (11), and should be a neutral molecule.”
UniChem: extension of InChI-based compound mapping to salt, connectivity and stereochemistry layers (2014, background): “The original developers of the InChI foresaw exactly this issue [2], and deliberately designed the InChI in such a way such that molecules could be compared on different levels of structural specification.”
MetFrag relaunched: incorporating strategies beyond in silico fragmentation (2016, background): “2 output (InChIs, SMILES, SDF) (9)log PUnknown = a · RTUnknown + b (10)SCRT = 1 σ √ 2π e−(|log PUnknown−log PC”