compound 66 [PMID: 21802293]   Click here for help

GtoPdb Ligand ID: 8212

Compound class: Synthetic organic
Comment: Compound 66 is reported in [1], a medicinal chemistry/structure-based design study to identify improved inhibitors of BRAFV600E.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 134.45
Molecular weight 477.07
XLogP 4.01
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
Click here for help

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/)

✖
Canonical SMILES COc1n[nH]c2c1cc(cn2)NC(=O)c1c(F)ccc(c1F)NS(=O)(=O)c1cccc(c1)F
Isomeric SMILES COc1n[nH]c2c1cc(cn2)NC(=O)c1c(F)ccc(c1F)NS(=O)(=O)c1cccc(c1)F
InChI InChI=1S/C20H14F3N5O4S/c1-32-20-13-8-11(9-24-18(13)26-27-20)25-19(29)16-14(22)5-6-15(17(16)23)28-33(30,31)12-4-2-3-10(21)7-12/h2-9,28H,1H3,(H,25,29)(H,24,26,27)
InChI Key WGFNXGPBPIJYLI-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
Compound 66 inhibits the activity of BRAFV600E with an IC50 value of 0.7nM [1]. In the presence of 1μM compound 66, FGR, Src, FLT3, LCK, PTK6 and SRMS kinase activities are inhibited by >75% [1].
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
src-related kinase lacking C-terminal regulatory tyrosine and N-terminal myristylation sites Hs Inhibitor Inhibition - - - 1
⤷ [1]
Description: Measured as % inhibition using 1μM compound.