{
  "abstract": "Molecular and reaction fingerprints are widely used as static descriptors, but their relationship to graph-level reaction application remains unclear. We address this question in counted Extended-Connectivity Fingerprint (ECFP) space, representing reactions as signed differences between product and substrate fingerprints. We define ECFP-compatible templates, for which graph-level reaction application induces a constant fingerprint displacement, yielding a functorial mapping from graph transformations to affine translations in fingerprint space. We also introduce reaction-center ECFPs to encode the local environments required for template application and to provide a fast coordinate-wise prefilter for graph-level reaction applicability. We evaluate this framework on USPTO-50k and MetaNetX reactions across a range of ECFP radii. Both representations carry predictive information for reaction-class and enzyme-class classification, with reaction-center ECFPs contributing information not captured by reaction ECFPs alone. This framework connects reaction templates and reaction fingerprints to molecular pathway search and reaction-property prediction in fingerprint space.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 4,
  "authors": [
    {
      "name": "Philippe Meyer"
    },
    {
      "name": "Thomas Duigou"
    },
    {
      "name": "Guillaume Gricourt"
    },
    {
      "name": "Jean-Loup Faulon"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/79w7y8jyggh3r.bib",
  "cited_by": 0,
  "doi": "10.1186/s13321-026-01322-2",
  "fulltext_url": null,
  "id": "79w7y8jyggh3r",
  "issns": [
    "1758-2946"
  ],
  "landing_url": "https://link.springer.com/article/10.1186/s13321-026-01322-2",
  "language": null,
  "licence": "CC-BY-4.0",
  "licence_label": "CC BY 4.0",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [],
  "openalex": null,
  "pdf_url": null,
  "pmcid": null,
  "pmid": null,
  "published": "2026-11-06",
  "publisher": "Springer Science and Business Media LLC",
  "ris": "https://research.draconitic.com/paper/79w7y8jyggh3r.ris",
  "sources": [
    {
      "first_seen": "2026-11-07T00:21:10Z",
      "native_id": "10.1186/s13321-026-01322-2",
      "source": "crossref",
      "url": "https://link.springer.com/article/10.1186/s13321-026-01322-2"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "issn:1758-2946",
      "subfield": "theoretical"
    }
  ],
  "title": "Representing chemical and enzymatic reactions in fingerprint space for applicability filtering and classification",
  "title_text": "Representing chemical and enzymatic reactions in fingerprint space for applicability filtering and classification",
  "type": "peer-reviewed",
  "updated_at": "2026-11-08T00:22:10Z",
  "url": "https://research.draconitic.com/paper/79w7y8jyggh3r",
  "venue": "Journal of Cheminformatics",
  "versions": [
    {
      "doi": "10.26434/chemrxiv.15006884/v1",
      "pid": null,
      "relation": "preprint",
      "title": null,
      "venue": null
    }
  ]
}