GSK690693   Click here for help

GtoPdb Ligand ID: 5196

Synonyms: compound 3g [PMID 18800763] | GSK 690693 | GSK-690693
PDB Ligand
Compound class: Synthetic organic
Comment: GSK-690693 is an ATP competitive, pan-AKT kinase inhibitor [2-3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 137.14
Molecular weight 425.22
XLogP 1.99
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCn1c(nc2c1c(OCC1CCCNC1)cnc2C#CC(O)(C)C)c1nonc1N
Isomeric SMILES CCn1c(nc2c1c(OC[C@H]1CCCNC1)cnc2C#CC(O)(C)C)c1nonc1N
InChI InChI=1S/C21H27N7O3/c1-4-28-18-15(30-12-13-6-5-9-23-10-13)11-24-14(7-8-21(2,3)29)16(18)25-20(28)17-19(22)27-31-26-17/h11,13,23,29H,4-6,9-10,12H2,1-3H3,(H2,22,27)/t13-/m0/s1
InChI Key KGPGFQWBCSZGEL-ZDUSSCGKSA-N
Bioactivity Comments
GSK-690693 inhibits other AGC family kinases due to their shared ATP domain structure (eg MSK1, ROCK1, and RSK, and to a lesser extent PKA, PrkX, and PKC isozymes) [2]. CAMK family kinases AMPK and DAPK3 and STE family kinases PAK4, 5, and 6 are also inhibited by GSK-690693 [2]. See Table 5 in Heerding et al (2008) [2] for IC50s for all kinases screened for GSK-690693 inhibition.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
AKT serine/threonine kinase 1 Primary target of this compound Hs Inhibitor Inhibition 8.7 pKd - 1
pKd 8.7 (Kd 2.2x10-9 M) [1]
protein kinase, cAMP-dependent, catalytic, beta subunit Hs Inhibitor Inhibition 7.9 pKd - 1
pKd 7.9 (Kd 1.3x10-8 M) [1]
protein kinase, cAMP-dependent, catalytic, alpha subunit Hs Inhibitor Inhibition 7.7 pKd - 1
pKd 7.7 (Kd 1.9x10-8 M) [1]
AKT serine/threonine kinase 1 Primary target of this compound Hs Inhibitor Inhibition 8.7 pIC50 - 2
pIC50 8.7 (IC50 2x10-9 M) [2]
protein kinase C theta Hs Inhibitor Inhibition 8.7 pIC50 - 2
pIC50 8.7 (IC50 2x10-9 M) [2]
protein kinase X-linked Hs Inhibitor Inhibition 8.3 pIC50 - 2
pIC50 8.3 (IC50 5x10-9 M) [2]
p21 (RAC1) activated kinase 6 Hs Inhibitor Inhibition 8.2 pIC50 - 2
pIC50 8.2 (IC50 6x10-9 M) [2]
Description: Data from binding assays.
AKT serine/threonine kinase 3 Primary target of this compound Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 9x10-9 M) [2]
p21 (RAC1) activated kinase 4 Hs Inhibitor Inhibition 8.0 pIC50 - 2
pIC50 8.0 (IC50 1x10-8 M) [2]
Description: Data from binding assays.
AKT serine/threonine kinase 2 Primary target of this compound Hs Inhibitor Inhibition 7.9 pIC50 - 2
pIC50 7.9 (IC50 1.3x10-8 M) [2]
Protein kinase G (PKG) 1 Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 3.3x10-8 M) [2]
p21 (RAC1) activated kinase 5 Hs Inhibitor Inhibition 7.3 pIC50 - 2
pIC50 7.3 (IC50 5.2x10-8 M) [2]