{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,24]],"date-time":"2026-01-24T16:03:08Z","timestamp":1769270588922,"version":"3.49.0"},"reference-count":24,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T00:00:00Z","timestamp":1715644800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T00:00:00Z","timestamp":1715644800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["2020026"],"award-info":[{"award-number":["2020026"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","award":["654241"],"award-info":[{"award-number":["654241"]}],"id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001700","name":"Ministry of Education, Culture, Sports, Science and Technology","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001700","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001866","name":"Fonds National de la Recherche Luxembourg","doi-asserted-by":"publisher","award":["A18\/BM\/12341006"],"award-info":[{"award-number":["A18\/BM\/12341006"]}],"id":[{"id":"10.13039\/501100001866","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["J Cheminform"],"abstract":"<jats:sec>\n                <jats:title>Abstract<\/jats:title>\n                <jats:p>This work presents a proposed extension to the International Union of Pure and Applied Chemistry (IUPAC) International Chemical Identifier (InChI) standard that allows the representation of isotopically-resolved chemical entities at varying levels of ambiguity in isotope location. This extension includes an improved interpretation of the current isotopic layer within the InChI standard and a new isotopologue layer specification for representing chemical intensities with ambiguous isotope localization. Both improvements support the unique isotopically-resolved chemical identification of features detected and measured in analytical instrumentation, specifically nuclear magnetic resonance and mass spectrometry.<\/jats:p>\n              <\/jats:sec><jats:sec>\n                <jats:title>Scientific contribution<\/jats:title>\n                <jats:p>This new extension to the InChI standard would enable improved annotation of analytical datasets characterizing chemical entities, supporting the FAIR (Findable, Accessible, Interoperable, and Reusable) guiding principles of data stewardship for chemical datasets, ultimately promoting Open Science in chemistry.<\/jats:p>\n              <\/jats:sec>","DOI":"10.1186\/s13321-024-00847-8","type":"journal-article","created":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T01:02:18Z","timestamp":1715648538000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["InChI isotopologue and isotopomer specifications"],"prefix":"10.1186","volume":"16","author":[{"given":"Hunter N. B.","family":"Moseley","sequence":"first","affiliation":[]},{"given":"Philippe","family":"Rocca-Serra","sequence":"additional","affiliation":[]},{"given":"Reza M.","family":"Salek","sequence":"additional","affiliation":[]},{"given":"Masanori","family":"Arita","sequence":"additional","affiliation":[]},{"given":"Emma L.","family":"Schymanski","sequence":"additional","affiliation":[]}],"member":"297","published-online":{"date-parts":[[2024,5,14]]},"reference":[{"issue":"1","key":"847_CR1","doi-asserted-by":"publisher","first-page":"7","DOI":"10.1186\/1758-2946-5-7","volume":"5","author":"S Heller","year":"2013","unstructured":"Heller S, McNaught A, Stein S, Tchekhovskoi D, Pletnev I (2013) InChI-the worldwide chemical structure identifier standard. J Cheminform 5(1):7","journal-title":"J Cheminform"},{"issue":"1","key":"847_CR2","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s13321-015-0068-4","volume":"7","author":"SR Heller","year":"2015","unstructured":"Heller SR, McNaught A, Pletnev I, Stein S, Tchekhovskoi D (2015) InChI, the IUPAC international chemical identifier. J Cheminform 7(1):1\u201334","journal-title":"J Cheminform"},{"issue":"1","key":"847_CR3","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s13321-021-00517-z","volume":"13","author":"JM Goodman","year":"2021","unstructured":"Goodman JM, Pletnev I, Thiessen P, Bolton E, Heller SR (2021) InChI version 1.06: now more than 99.99% reliable. J Cheminform 13(1):1\u20138","journal-title":"J Cheminform"},{"key":"847_CR4","doi-asserted-by":"publisher","first-page":"223","DOI":"10.1007\/BFb0062536","volume-title":"Combinatorial mathematics","author":"BD McKay","year":"1978","unstructured":"McKay BD (1978) Computing automorphisms and canonical labellings of graphs. Combinatorial mathematics. Springer, New York, pp 223\u2013232"},{"key":"847_CR5","doi-asserted-by":"publisher","first-page":"94","DOI":"10.1016\/j.jsc.2013.09.003","volume":"60","author":"BD McKay","year":"2014","unstructured":"McKay BD, Piperno A (2014) Practical graph isomorphism, II. J Symb Comput 60:94\u2013112","journal-title":"J Symb Comput"},{"issue":"1","key":"847_CR6","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1186\/1758-2946-2-1","volume":"2","author":"S Heller","year":"2010","unstructured":"Heller S, McNaught A (2010) The status of the InChI project and the InChI trust. J Cheminform 2(1):1\u20131","journal-title":"J Cheminform"},{"key":"847_CR7","unstructured":"IUPAC\/InChI-trust licence for the international chemical identifier (InChI) software. https:\/\/www.inchi-trust.org\/wp\/download\/106\/LICENCE.pdf"},{"issue":"1","key":"847_CR8","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s13321-018-0277-8","volume":"10","author":"G Grethe","year":"2018","unstructured":"Grethe G, Blanke G, Kraut H, Goodman JM (2018) International chemical identifier for reactions (RInChI). J Cheminform 10(1):1\u20139","journal-title":"J Cheminform"},{"issue":"1","key":"847_CR9","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s13321-019-0357-4","volume":"11","author":"AM Clark","year":"2019","unstructured":"Clark AM, McEwen LR, Gedeck P, Bunin BA (2019) Capturing mixture composition: an open machine-readable format for representing mixed substances. J Cheminform 11(1):1\u201317","journal-title":"J Cheminform"},{"issue":"12","key":"847_CR10","doi-asserted-by":"publisher","first-page":"7448","DOI":"10.1021\/acs.est.2c00321","volume":"56","author":"A Lai","year":"2022","unstructured":"Lai A, Clark AM, Escher BI, Fernandez M, McEwen LR, Tian Z, Wang Z, Schymanski EL (2022) The next frontier of environmental unknowns: substances of unknown or variable composition, complex reaction products, or biological materials (UVCBs). Environ Sci Technol 56(12):7448\u20137466","journal-title":"Environ Sci Technol"},{"issue":"12","key":"847_CR11","doi-asserted-by":"publisher","first-page":"2493","DOI":"10.3390\/nano10122493","volume":"10","author":"I Lynch","year":"2020","unstructured":"Lynch I, Afantitis A, Exner T, Himly M, Lobaskin V, Doganis P, Maier D, Sanabria N, Papadiamantis AG, Rybinska-Fryca A (2020) Can an InChI for nano address the need for a simplified representation of complex nanomaterials across experimental and nanoinformatics studies? Nanomaterials 10(12):2493","journal-title":"Nanomaterials"},{"key":"847_CR12","doi-asserted-by":"publisher","DOI":"10.1038\/sdata.2016.18","volume":"3","author":"MD Wilkinson","year":"2016","unstructured":"Wilkinson MD, Dumontier M, Aalbersberg IJ, Appleton G, Axton M, Baak A, Blomberg N, Boiten J-W, da Silva Santos LB, Bourne PE (2016) The FAIR guiding principles for scientific data management and stewardship. Sci Data 3:160018","journal-title":"Sci Data"},{"key":"847_CR13","unstructured":"National Academies of Sciences E, Medicine (2018) Open science by design: realizing a vision for 21st century research"},{"key":"847_CR14","doi-asserted-by":"publisher","first-page":"428","DOI":"10.1016\/j.jbusres.2017.12.043","volume":"88","author":"R Vicente-Saez","year":"2018","unstructured":"Vicente-Saez R, Martinez-Fuentes C (2018) Open science now: a systematic literature review for an integrated definition. J Bus Res 88:428\u2013436","journal-title":"J Bus Res"},{"issue":"3","key":"847_CR15","doi-asserted-by":"publisher","first-page":"25","DOI":"10.1515\/ci-2017-0307","volume":"39","author":"S Chalk","year":"2017","unstructured":"Chalk S, McEwen L (2017) The IUPAC gold book. Chem Int 39(3):25\u201330","journal-title":"Chem Int"},{"key":"847_CR16","unstructured":"Chalk SJ (2019) The IUPAC gold book website. https:\/\/goldbook.iupac.org\/. Accessed 01 Feb 2018"},{"key":"847_CR17","doi-asserted-by":"publisher","unstructured":"Constitutional isomerism definition in the IUPAC gold book. https:\/\/doi.org\/10.1351\/goldbook.C01285. Accessed 01 Feb 2018","DOI":"10.1351\/goldbook.C01285"},{"key":"847_CR18","unstructured":"Structural isomer entry in Wikipedia. https:\/\/en.wikipedia.org\/wiki\/Structural_isomer. Accessed 01 Feb 2018"},{"key":"847_CR19","doi-asserted-by":"publisher","unstructured":"Stereoisomers definition in the IUPAC gold book. https:\/\/doi.org\/10.1351\/goldbook.S05984. Accessed 01 Feb 2018","DOI":"10.1351\/goldbook.S05984"},{"key":"847_CR20","unstructured":"Stereoisomerism entry in Wikipedia. https:\/\/en.wikipedia.org\/wiki\/Stereoisomerism. Accessed 01 Feb 2018"},{"key":"847_CR21","doi-asserted-by":"publisher","unstructured":"Isotopomer definition in the IUPAC gold book. https:\/\/doi.org\/10.1351\/goldbook.I03352. Accessed 01 Feb 2018","DOI":"10.1351\/goldbook.I03352"},{"key":"847_CR22","unstructured":"Isotopomers definition in Wikipedia. https:\/\/goldbook.iupac.org\/. Accessed 01 Feb 2018"},{"key":"847_CR23","doi-asserted-by":"publisher","unstructured":"Isotopologue definition in the IUPAC gold book. https:\/\/doi.org\/10.1351\/goldbook.I03351. Accessed 01 Feb 2018","DOI":"10.1351\/goldbook.I03351"},{"key":"847_CR24","unstructured":"Isotopologue entry in Wikipedia. https:\/\/goldbook.iupac.org\/. Accessed 01 Feb 2018"}],"container-title":["Journal of Cheminformatics"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s13321-024-00847-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1186\/s13321-024-00847-8\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s13321-024-00847-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,5,14]],"date-time":"2024-05-14T01:03:11Z","timestamp":1715648591000},"score":1,"resource":{"primary":{"URL":"https:\/\/jcheminf.biomedcentral.com\/articles\/10.1186\/s13321-024-00847-8"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,5,14]]},"references-count":24,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["847"],"URL":"https:\/\/doi.org\/10.1186\/s13321-024-00847-8","relation":{},"ISSN":["1758-2946"],"issn-type":[{"value":"1758-2946","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,5,14]]},"assertion":[{"value":"8 December 2023","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"27 April 2024","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"14 May 2024","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"The authors have no competing interests.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"54"}}