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Molecular Diversity

, Volume 21, Issue 4, pp 779–789 | Cite as

Cheminformatic characterization of natural products from Panama

  • Dionisio A. OlmedoEmail author
  • Mariana González-Medina
  • Mahabir P. Gupta
  • José L. Medina-FrancoEmail author
Original Article

Abstract

In this work, we discuss the characterization and diversity analysis of 354 natural products (NPs) from Panama, systematically analyzed for the first time. The in-house database was compared to NPs from Brazil, compounds from Traditional Chinese Medicine, natural and semisynthetic collections used in high-throughput screening, and compounds from ChEMBL. An analysis of the “global diversity” was conducted using molecular properties of pharmaceutical interest, three molecular fingerprints of different design, molecular scaffolds, and molecular complexity. The global diversity was visualized using consensus diversity plots that revealed that the secondary metabolites in the Panamanian flora have a large scaffold diversity as compared to other composite databases and also have several unique scaffolds. The large scaffold diversity is in agreement with the broad range of biological activities that this collection of NPs from Panama has shown. This study also provided further quantitative evidence of the large structural complexity of NPs. The results obtained in this study support that NPs from Panama are promising candidates to identify selective molecules and are suitable sources of compounds for virtual screening campaigns.

Keywords

Cheminformatics Chemical space Chemical diversity Consensus diversity plots Natural products Structural similarity Panamanian biodiversity 

Abbreviations

NPs

Natural products

CIFPMA

NPs database of CIFLORPAN, The University of Panama, Republic of Panama

UEFS

NPs database of UEFS, The State University of Feira De Santana, Bahia, Brazil

MEGx

NPs screening compounds

NATx

Semisynthetic screening compounds

TCM

Traditional Chinese Medicine, Taiwan

CDPs

Consensus diversity plots

ECFP

Extended connectivity fingerprints

MACCS

Molecular Access System keys

CDF

Cumulative distribution function

MOE

Molecular operating environment

PCA

Principal component analysis

MEQI

Molecular equivalent indices

CSR

Cyclic system recovery

Mol. Glob.

Molecular globularity

\(\hbox {Fsp}^{3}\)

Fraction of sp3-hybridized atoms

FCC

Fraction of chiral centers

PMI

Principal moment of inertia

NRP

Ratio of normalized moment of inertia

Notes

Acknowledgements

We thank the Faculty of Chemistry of the Univer sidad Nacional Autónoma de México for granting a postdoctoral stay. Authors thank the research group DIFACQUIM for their collaboration. DAO thanks the Office of Vice President for Academic affairs of the University of Panama for granting paid leave of absence for the accomplishment of the postdoctoral internship at UNAM. MPG and DAO acknowledge SNI awards from SENACYT of Panama. We also thank funding from the ‘Programa de Apoyo a la Investigaciónn y el Posgrado (PAIP) 50009163, Facultad de Química, UNAM.

Compliance with ethical standards

Conflict of interest

Authors declare that there is no financial or commercial conflict of interest.

Supplementary material

11030_2017_9781_MOESM1_ESM.pdf (628 kb)
Supplementary material 1 (pdf 627 KB)

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Copyright information

© Springer International Publishing AG 2017

Authors and Affiliations

  1. 1.CIFLORPAN, Center for Pharmacognostic Research on Panamanian Flora, College of PharmacyUniversity of PanamaPanama CityRepublic of Panama
  2. 2.Departamento de Farmacia, Facultad de QuímicaUniversidad Nacional Autónoma de MéxicoMexico CityMexico

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