fruquintinib   Click here for help

GtoPdb Ligand ID: 9428

Synonyms: Elunate® | HMPL-013 | HMPL013
Approved drug
fruquintinib is an approved drug (China (2018))
Compound class: Synthetic organic
Comment: Fruquintinib (HMPL-013) is a potent and selective inhibitor of VEGFR 1, 2, 3 tyrosine kinases, being developed for potential antineoplastic efficacy [1]; preclinical data is reported in this reference.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 95.71
Molecular weight 393.13
XLogP 2.46
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CNC(=O)c1c(C)oc2c1ccc(c2)Oc1ncnc2c1cc(OC)c(c2)OC
Isomeric SMILES CNC(=O)c1c(C)oc2c1ccc(c2)Oc1ncnc2c1cc(OC)c(c2)OC
InChI InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)
InChI Key BALLNEJQLSTPIO-UHFFFAOYSA-N
Bioactivity Comments
HMPL-013 shows only weak inhibition of RET (IC50 128nM), FGFR-1 (IC50 181nM) and c-kit (IC50 458nM) kinases in a biochemical selectivity screen. Weak inhbition of FGFR-1 was replicated in a cellular assay measuring bFGF stimulated FGFR-1 phosphorylation [1].
Selectivity at catalytic receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
fms related receptor tyrosine kinase 4 Primary target of this compound Hs Inhibitor Inhibition 9.3 pIC50 - 1
pIC50 9.3 (IC50 5x10-10 M) [1]
Description: Evaluated in a [32]p-ATP incorporation assay
kinase insert domain receptor Primary target of this compound Hs Inhibitor Inhibition 7.5 – 7.6 pIC50 - 1
pIC50 7.6 (IC50 2.5x10-8 M) [1]
Description: Evaluated in a Z-lyte assay.
pIC50 7.5 (IC50 3.5x10-8 M) [1]
Description: Evaluated in a [32]p-ATP incorporation assay
fms related receptor tyrosine kinase 1 Primary target of this compound Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3.3x10-8 M) [1]
Description: Evaluated in a [32]p-ATP incorporation assay