compound 2c [PMID: 24900538]   Click here for help

GtoPdb Ligand ID: 8138

Compound class: Synthetic organic
Comment: Compound 2c is one of the analogues identified by a medicinal chemistry approach to identify neurotrophic tyrosine kinase, receptor, type 1 (TrkA) inhibitors [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 93.02
Molecular weight 381.17
XLogP 4.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(Oc1[nH]nc(c1)n1cnc2c1nc(cc2)NC(c1ccc(cn1)F)C)C
Isomeric SMILES CC(Oc1[nH]nc(c1)n1cnc2c1nc(cc2)N[C@H](c1ccc(cn1)F)C)C
InChI InChI=1S/C19H20FN7O/c1-11(2)28-18-8-17(25-26-18)27-10-22-15-6-7-16(24-19(15)27)23-12(3)14-5-4-13(20)9-21-14/h4-12H,1-3H3,(H,23,24)(H,25,26)/t12-/m0/s1
InChI Key FZBVNCFBCNXULH-LBPRGKRZSA-N
Bioactivity Comments
The interactions below are those with IC50s < 10nM. Compound 2c inhibits the activity of additional kinases with higher IC50 values (10-100nM) [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
ABL proto-oncogene 1, non-receptor tyrosine kinase Hs Inhibitor Inhibition 8.9 pIC50 - 1
pIC50 8.9 (IC50 1.2x10-9 M) [1]
FGR proto-oncogene, Src family tyrosine kinase Hs Inhibitor Inhibition 8.7 pIC50 - 1
pIC50 8.7 (IC50 2.2x10-9 M) [1]
Bruton tyrosine kinase Hs Inhibitor Inhibition 8.5 pIC50 - 1
pIC50 8.5 (IC50 3.5x10-9 M) [1]
salt inducible kinase 1 Hs Inhibitor Inhibition 8.3 pIC50 - 1
pIC50 8.3 (IC50 5.5x10-9 M) [1]
phosphorylase kinase catalytic subunit gamma 2 Hs Inhibitor Inhibition 8.2 pIC50 - 1
pIC50 8.2 (IC50 6.1x10-9 M) [1]
testis specific serine kinase 2 Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3.06x10-8 M) [1]
WNK lysine deficient protein kinase 3 Hs Inhibitor Inhibition 7.0 pIC50 - 1
pIC50 7.0 (IC50 9.98x10-8 M) [1]
Selectivity at catalytic receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
neurotrophic receptor tyrosine kinase 1 Primary target of this compound Hs Inhibitor Inhibition 8.9 pIC50 - 1
pIC50 8.9 (IC50 1.4x10-9 M) [1]
fms related receptor tyrosine kinase 3 Hs Inhibitor Inhibition 8.7 pIC50 - 1
pIC50 8.7 (IC50 2.1x10-9 M) [1]
fibroblast growth factor receptor 1 Hs Inhibitor Inhibition 8.1 pIC50 - 1
pIC50 8.1 (IC50 8.7x10-9 M) [1]