lifirafenib   Click here for help

GtoPdb Ligand ID: 8958

Synonyms: BGB-283 | compound 2.2b [3]
PDB Ligand
Compound class: Synthetic organic
Comment: Lifirafenib (BGB-283) is an investigational inhibitor of the Raf kinases (ARAF, BRAF, CRAF) and the epidermal growth factor receptor (EGFR) tyrosine kinase [2]. BGB-283 is being investigated for its antineoplastic potential, particularly in tumours that are driven by RAF/MAPK pathway activation, including maliganacies with gain-of-function BRAFV600 mutations. The compound is one of the structures claimed in patent WO2013097224 A1 [3].
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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.

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View interactive charts of activity data across species

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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 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 89.13
Molecular weight 478.13
XLogP 3.33
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 O=C1CCc2c(N1)nccc2Oc1ccc2c(c1)C1C(O2)C1c1nc2c([nH]1)cc(cc2)C(F)(F)F
Isomeric SMILES O=C1CCc2c(N1)nccc2Oc1ccc2c(c1)[C@@H]1[C@H](O2)[C@H]1c1nc2c([nH]1)cc(cc2)C(F)(F)F
InChI InChI=1S/C25H17F3N4O3/c26-25(27,28)11-1-4-15-16(9-11)31-24(30-15)21-20-14-10-12(2-5-17(14)35-22(20)21)34-18-7-8-29-23-13(18)3-6-19(33)32-23/h1-2,4-5,7-10,20-22H,3,6H2,(H,30,31)(H,29,32,33)/t20-,21-,22-/m0/s1
InChI Key NGFFVZQXSRKHBM-FKBYEOEOSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[[(1R,1aS,6bR)-1-[6-(trifluoromethyl)-1H-benzimidazol-2-yl]-1a,6b-dihydro-1H-cyclopropa[b][1]benzofuran-5-yl]oxy]-3,4-dihydro-1H-1,8-naphthyridin-2-one
International Nonproprietary Names Click here for help
INN number INN
10554 lifirafenib
Synonyms Click here for help
BGB-283 | compound 2.2b [3]
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9657033
Reactome Reaction Reactome logo R-HSA-6802938
Other databases
GtoPdb PubChem SID 310264739
PubChem CID 89670174
RCSB PDB Ligand 3K3
Search Google for chemical match using the InChIKey NGFFVZQXSRKHBM-FKBYEOEOSA-N
Search Google for chemicals with the same backbone NGFFVZQXSRKHBM
Search PubMed clinical trials lifirafenib
Search PubMed titles lifirafenib
Search PubMed titles/abstracts lifirafenib
SynPHARM 83246 (in complex with B-Raf proto-oncogene, serine/threonine kinase)
UniChem Compound Search for chemical match using the InChIKey NGFFVZQXSRKHBM-FKBYEOEOSA-N
UniChem Connectivity Search for chemical match using the InChIKey NGFFVZQXSRKHBM-FKBYEOEOSA-N

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MedChemExpress
Lifirafenib (links to external site)
Cat. No. HY-18957