LUT014   Click here for help

GtoPdb Ligand ID: 11568

Synonyms: LUT-014
Compound class: Synthetic organic
Comment: LUT014 is a BRAF inhibitor [1]. BRAF is a component of the signalling pathway utilised by the EGFR. Inhibiting mutant BRAF in cancer cells leads to tumour shrinkage, whereas in normal cells the mitogen-activated protein kinase (MAPK) pathway is activated and proliferation is induced. This latter paradoxical effect of BRAF inhibition is being exploited to reverse inhibition of the MAPK pathway by EGFR inhibitors which is responsible for dose-limiting skin toxicity (acneiform rash) in patients treated with EGFR-targeting anti-tumour agents such as cetuximab or panitumumab.
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species
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 CDK toolkit. 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 113.53
Molecular weight 528.16
XLogP 5.82
No. Lipinski's rules broken 1
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.

✖
Canonical SMILES Cc1ccc2c(c1Nc1ncccc1c1ncnc3c1[nH]cn3)ccnc2Nc1cccc(c1)OC(F)(F)F
Isomeric SMILES Cc1ccc2c(c1Nc1ncccc1c1ncnc3c1[nH]cn3)ccnc2Nc1cccc(c1)OC(F)(F)F
InChI InChI=1S/C27H19F3N8O/c1-15-7-8-19-18(9-11-32-24(19)37-16-4-2-5-17(12-16)39-27(28,29)30)21(15)38-25-20(6-3-10-31-25)22-23-26(35-13-33-22)36-14-34-23/h2-14H,1H3,(H,31,38)(H,32,37)(H,33,34,35,36)
InChI Key FZPYULHBUBXPIG-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
6-methyl-5-N-[3-(7H-purin-6-yl)pyridin-2-yl]-1-N-[3-(trifluoromethoxy)phenyl]isoquinoline-1,5-diamine
Synonyms Click here for help
LUT-014
Database Links Click here for help
CAS Registry No. 2274819-46-2 (source: PubChem)
GtoPdb PubChem SID 441604940
PubChem CID 138319775
Search Google for chemical match using the InChIKey FZPYULHBUBXPIG-UHFFFAOYSA-N
Search Google for chemicals with the same backbone FZPYULHBUBXPIG
UniChem Compound Search for chemical match using the InChIKey FZPYULHBUBXPIG-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey FZPYULHBUBXPIG-UHFFFAOYSA-N