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compound 33 [PMID: 40529071]   Click here for help

GtoPdb Ligand ID: 13976

Compound class: Synthetic organic
Comment: Compound 33 was identified in a structure-activity-relationship (SAR) study to improve the potency and selectivity of a series of triazolopyrimidine compounds with antimycobacterial activity [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 61.58
Molecular weight 387.36
XLogP 3.92
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1=CC=C(C2=NC3=NN=CN3C(=C2)NCCC4=CC=C(C=C4)C(F)(F)F)O1
Isomeric SMILES CC1=CC=C(O1)C2=NC3=NN=CN3C(NCCC4=CC=C(C=C4)C(F)(F)F)=C2
InChI InChI=1S/C19H16F3N5O/c1-12-2-7-16(28-12)15-10-17(27-11-24-26-18(27)25-15)23-9-8-13-3-5-14(6-4-13)19(20,21)22/h2-7,10-11,23H,8-9H2,1H3
InChI Key YXRAZWFVNHVBGD-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
The MIC90 for antimycobacterial activity against M. tuberculosis is 0.37 μM in vitro [1]. Compound 33 demonstrates low cellular toxicity in vitro, with a CC50 >100 μM for HepG2 human cells [1].