balanol   Click here for help

GtoPdb Ligand ID: 8142

Synonyms: azepinostatin
PDB Ligand
Comment: Balanol is a fungal metabolite which acts as a non-selective ATP-competitive inhibitor of protein kinases A, G and C (AGC family kinases) [1-3]. Balanol is also reported to inhibit G protein-coupled receptor kinases (GRKs), with modest selectivity for the GRK2 family members, GRK2 and GRK3 [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 7
Rotatable bonds 9
Topological polar surface area 202.72
Molecular weight 550.16
XLogP 4.2
No. Lipinski's rules broken 1
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Canonical SMILES Oc1ccc(cc1)C(=O)NC1CNCCCC1OC(=O)c1cc(O)c(c(c1)O)C(=O)c1c(O)cccc1C(=O)O
Isomeric SMILES Oc1ccc(cc1)C(=O)N[C@@H]1CNCCC[C@H]1OC(=O)c1cc(O)c(c(c1)O)C(=O)c1c(O)cccc1C(=O)O
InChI InChI=1S/C28H26N2O10/c31-16-8-6-14(7-9-16)26(36)30-18-13-29-10-2-5-22(18)40-28(39)15-11-20(33)24(21(34)12-15)25(35)23-17(27(37)38)3-1-4-19(23)32/h1,3-4,6-9,11-12,18,22,29,31-34H,2,5,10,13H2,(H,30,36)(H,37,38)/t18-,22-/m1/s1
Bioactivity Comments
IC50 values for banalol inhibition of GRK1 and GRK3 subfamily members are reported by Tesmer et al (2010) [4], in Table 1. We have mapped PKCη as the primary target of balanol, based only on its virtue of having the lowest IC50 value. The interaction table below makes clear the broad spectrum activity of this compound.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
protein kinase A Rn Inhibitor Inhibition 10.4 pIC50 - 1
pIC50 10.4 (IC50 4x10-11 M) [1]
Description: Inhibition of PKA extracted from rat brain homogenate.
protein kinase C eta Primary target of this compound Hs Inhibitor Inhibition 8.5 pIC50 - 1
pIC50 8.5 (IC50 3x10-9 M) [1]
protein kinase C beta Hs Inhibitor Inhibition 8.0 pIC50 - 1
pIC50 8.0 (IC50 1x10-8 M) [1]
protein kinase C gamma Hs Inhibitor Inhibition 8.0 pIC50 - 1
pIC50 8.0 (IC50 1x10-8 M) [1]
protein kinase C delta Hs Inhibitor Inhibition 7.8 pIC50 - 1
pIC50 7.8 (IC50 1.6x10-8 M) [1]
protein kinase C epsilon Hs Inhibitor Inhibition 7.7 pIC50 - 1
pIC50 7.7 (IC50 2x10-8 M) [1]
protein kinase C alpha Hs Inhibitor Inhibition 7.5 pIC50 - 1
pIC50 7.5 (IC50 3x10-8 M) [1]
beta adrenergic receptor kinase 1 Hs Inhibitor Inhibition 7.4 pIC50 - 4
pIC50 7.4 (IC50 4.2x10-8 M) [4]
Description: Inhibition of tubulin phosphorylation by balanol.
beta adrenergic receptor kinase 2 Hs Inhibitor Inhibition 7.3 pIC50 - 4
pIC50 7.3 (IC50 4.7x10-8 M) [4]
G protein-coupled receptor kinase 7 Hs Inhibitor Inhibition 6.7 pIC50 - 4
pIC50 6.7 (IC50 1.8x10-7 M) [4]
G protein-coupled receptor kinase 4 Hs Inhibitor Inhibition 6.6 pIC50 - 4
pIC50 6.6 (IC50 2.6x10-7 M) [4]
Description: Measuring inhibition of human GRK-4-mediated phosphorylation of bovine tubulin dimers.
G protein-coupled receptor kinase 1 Hs Inhibitor Inhibition 6.5 pIC50 - 4
pIC50 6.5 (IC50 3.4x10-7 M) [4]
G protein-coupled receptor kinase 6 Hs Inhibitor Inhibition 6.3 pIC50 - 4
pIC50 6.3 (IC50 4.9x10-7 M) [4]
protein kinase C zeta Hs Inhibitor Inhibition 5.2 pIC50 - 1
pIC50 5.2 (IC50 5.9x10-6 M) [1]