lifirafenib   Click here for help

GtoPdb Ligand ID: 8958

Synonyms: BGB-283 | compound 2.2b [2]
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 [1]. BGB-283 is being investigated for its antineoplastic activity. The compound is one of the structures described in patent WO2013097224 A1 [2].
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2D Structure
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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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
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 [2]
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
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SynPHARM 83246 (in complex with B-Raf proto-oncogene, serine/threonine kinase)