title: Chemoinformatic expedition of the chemical space of fungal products.
abstract: Fungi are valuable resources for bioactive secondary metabolites. However, the chemical space of fungal secondary metabolites has been studied only on a limited basis. Herein, we report a comprehensive chemoinformatic analysis of a unique set of 207 fungal metabolites isolated and characterized in a USA National Cancer Institute funded drug discovery project.
  
  
  
  Comparison of the molecular complexity of the 207 fungal metabolites with approved anticancer and nonanticancer drugs, compounds in clinical studies, general screening compounds and molecules Generally Recognized as Safe revealed that fungal metabolites have high degree of complexity. Molecular fingerprints showed that fungal metabolites are as structurally diverse as other natural products and have, in general, drug-like physicochemical properties.
  
  
  
  Fungal products represent promising candidates to expand the medicinally relevant chemical space. This work is a significant expansion of an analysis reported years ago for a smaller set of compounds (less than half of the ones included in the present work) from filamentous fungi using different structural properties.
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: Mariana
authors.initials: M
authors.lastname: González-Medina
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: Fernando D
authors.initials: FD
authors.lastname: Prieto-Martínez
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: J Jesús
authors.initials: JJ
authors.lastname: Naveja
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: Oscar
authors.initials: O
authors.lastname: Méndez-Lucio
authors.affiliation: Department of Medicinal Chemistry & Pharmacognosy, Faculty of Pharmacy, Jordan University of Science & Technology, PO Box 3030, Irbid 22110, Jordan.
authors.forename: Tamam
authors.initials: T
authors.lastname: El-Elimat
authors.affiliation: Mycosynthetix, Inc., 505 Meadowland Drive, Suite 103, Hillsborough, NC 27278, USA.
authors.forename: Cedric J
authors.initials: CJ
authors.lastname: Pearce
authors.affiliation: Department of Chemistry & Biochemistry, University of North Carolina at Greensboro, PO Box 26170, Greensboro, NC 27402, USA.
authors.forename: Nicholas H
authors.initials: NH
authors.lastname: Oberlies
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: Mario
authors.initials: M
authors.lastname: Figueroa
authors.affiliation: Facultad de Química, Departamento de Farmacia, Universidad Nacional Autónoma de México, Avenida Universidad 3000, México City 04510, México.
authors.forename: José L
authors.initials: JL
authors.lastname: Medina-Franco
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D019295:Computational Biology; D055808:Drug Discovery; D005658:Fungi / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy*
chemical_list: D000970:Antineoplastic Agents; D001688:Biological Products
keywords: chemical space; chemoinformatics; fungal metabolites; master key compound; molecular complexity; molecular fingerprint