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Glycomimetic Library

2 700 compounds

The main emphasis of library design was made on drug-like compounds enriched with H-bond donors (possess at least two H-bond donors) and bearing nature-like Fsp3–rich scaffolds with diverse spatial orientation of H-bond donors and different 3D-shapes. We suppose the library application would identify new attractive chemotypes which correspond to drug-/lead-like criteria and on the other hand participate in key interactions similar to glycoside binding in the active site of the targets.

Library design

  • Privileged core fragments and side chain functionalities:
    - cyclic amino alcohols, cyclic glycols
    - O,N-containing aliphatic rings
    - polyalcohols
  • Nature-likeness scoring algorithm: Taverna 2.5 workbench, similarity to available NP databases
  • MedChem structural filters, removal of common and trivial chemotypes: PAINS, REOS, Elli Lily rules and strict Enamine filters

Training set of known glycosides was collected from the public available e-databases, scientific literature and evaluated to define the optimal range of molecular parameters.

Parameters Range
MW 140 … 450
ClogP -3 … 4
Hb Donors 1 … 6
Hb Acceptors 2 … 10
TPSA 32 … 160 Å2
Ring count 1 … 5
Fsp3 0.3 … 1
S + Cl ≤ 2
Sulfo and Cyano group ≤ 1

Examples of compounds from Glycomimetic Library

Molecular properties of the Library

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