ruboxistaurin   Click here for help

GtoPdb Ligand ID: 5263

Synonyms: LY-333531
PDB Ligand
Compound class: Synthetic organic
Comment: The structure and activity of ruboxistaurin (as LY333531) is reported in [4]. Ruboxistaurin is selective for the PKC isozymes PKCβI and PKCβII compared to PKCα.
This compound is proposed to have therapeutic potential for treatment of nephropathy and vascular complications associated with diabetes mellitus [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 1
Rotatable bonds 2
Topological polar surface area 68.5
Molecular weight 468.22
XLogP 6.09
No. Lipinski's rules broken 1
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Canonical SMILES CN(CC1OCCn2cc(c3c2cccc3)C2=C(c3cn(CC1)c1ccccc31)C(=O)NC2=O)C
Isomeric SMILES CN(C[C@H]1OCCn2cc(c3c2cccc3)C2=C(c3cn(CC1)c1ccccc31)C(=O)NC2=O)C
InChI InChI=1S/C28H28N4O3/c1-30(2)15-18-11-12-31-16-21(19-7-3-5-9-23(19)31)25-26(28(34)29-27(25)33)22-17-32(13-14-35-18)24-10-6-4-8-20(22)24/h3-10,16-18H,11-15H2,1-2H3,(H,29,33,34)/t18-/m0/s1
Bioactivity Comments
Ruboxistaurin is considered as a PKCβ selective inhibitor [4-5], although there are reports that it also inhibits Pim-1 tyrosine kinase [3].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
protein kinase C beta Primary target of this compound Hs Inhibitor Inhibition 8.2 pIC50 - 4
pIC50 8.2 (IC50 5.9x10-9 M) [4]
Pim-1 proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition 6.7 pIC50 - 3
pIC50 6.7 (IC50 2x10-7 M) [3]
protein kinase C delta Hs Inhibitor Inhibition 6.6 pIC50 - 4
pIC50 6.6 (IC50 2.5x10-7 M) [4]
protein kinase C gamma Hs Inhibitor Inhibition 6.5 pIC50 - 4
pIC50 6.5 (IC50 3x10-7 M) [4]
protein kinase C alpha Hs Inhibitor Inhibition 6.4 pIC50 - 5
pIC50 6.4 (IC50 3.6x10-7 M) [5]
Pim-2 proto-oncogene, serine/threonine kinase Hs Inhibitor Inhibition <4.7 pIC50 - 3
pIC50 <4.7 (IC50 >2x10-5 M) [3]