title: Database fingerprint (DFP): an approach to represent molecular databases.
abstract: BACKGROUND
  Molecular fingerprints are widely used in several areas of chemoinformatics including diversity analysis and similarity searching. The fingerprint-based analysis of chemical libraries, in particular of large collections, usually requires the molecular representation of each compound in the library that may lead to issues of storage space and redundant calculations. In fact, information redundancy is inherent to the data, resulting on binary digit positions in the fingerprint without significant information.
  
  
  RESULTS
  Herein is proposed a general approach to represent an entire compound library with a single binary fingerprint. The development of the database fingerprint (DFP) is illustrated first using a short fingerprint (MACCS keys) for 10 data sets of general interest in chemistry. The application of the DFP is further shown with PubChem fingerprints for the data sets used in the primary example but with a larger number of compounds, up to 25,000 molecules. The performance of DFP were studied through differential Shannon entropy, k-mean clustering, and DFP/Tanimoto similarity.
  
  
  CONCLUSIONS
  The DFP is designed to capture key information of the compound collection and can be used to compare and assess the diversity of molecular libraries. This Preliminary Communication shows the potential of the novel fingerprint to conduct inter-library relationships. A major future goal is to apply the DFP for virtual screening and developing DFP for other data sets based on several different type of fingerprints.Graphical AbstractDatabase fingerprint captures the key information of molecular databases to perform chemical space characterization and virtual screening.
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico.
authors.forename: Eli
authors.initials: E
authors.lastname: Fernández-de Gortari
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico.|Escuela de Sistemas y Computación, Pontificia Universidad Católica del Ecuador Sede Esmeraldas (PUCESE), Esmeraldas, Ecuador.
authors.forename: César R
authors.initials: CR
authors.lastname: García-Jacas
authors.affiliation: Instituto de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico.
authors.forename: Karina
authors.initials: K
authors.lastname: Martinez-Mayorga
authors.affiliation: Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, Avenida Universidad 3000, 04510 Mexico City, Mexico.
authors.forename: José L
authors.identifier: 0000-0003-4940-1107
authors.initials: JL
authors.lastname: Medina-Franco
keywords: Diversity; Information content; Molecular fingerprints; Shannon entropy; Similarity