doramapimod   

GtoPdb Ligand ID: 5668

Synonyms: BIRB 796BS | BIRB-796 | BIRB796
Compound class: Synthetic organic
Comment: Doramapimod is an allosteric p38 MAP kinase inhibitor [2-3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 80.13
Molecular weight 527.29
XLogP 5.11
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(Nc1cc(nn1c1ccc(cc1)C)C(C)(C)C)Nc1ccc(c2c1cccc2)OCCN1CCOCC1
Isomeric SMILES O=C(Nc1cc(nn1c1ccc(cc1)C)C(C)(C)C)Nc1ccc(c2c1cccc2)OCCN1CCOCC1
InChI InChI=1S/C31H37N5O3/c1-22-9-11-23(12-10-22)36-29(21-28(34-36)31(2,3)4)33-30(37)32-26-13-14-27(25-8-6-5-7-24(25)26)39-20-17-35-15-18-38-19-16-35/h5-14,21H,15-20H2,1-4H3,(H2,32,33,37)
InChI Key MVCOAUNKQVWQHZ-UHFFFAOYSA-N
Bioactivity Comments
Doramapimod shows moderate selectivity for the p38α, -β and -γ isozymes compared to p38δ [2]. A Kd value of 0.1nM is reported in [3], but the authors do not specify subtype identity. In a screening panel of kinases, doramapimod inhibited many kinases with IC50 values <100nM (see Supplementary Information attached to [2]).
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
mitogen-activated protein kinase 14 Hs Inhibitor Inhibition 9.4 pKd - 1
pKd 9.4 (Kd 4.5x10-10 M) [1]
mitogen-activated protein kinase 11 Hs Inhibitor Inhibition 8.1 pIC50 - 2
pIC50 8.1 (IC50 7x10-9 M) [2]
Description: Inhibition of p38β2.
mitogen-activated protein kinase 14 Hs Inhibitor Inhibition 7.7 pIC50 - 2
pIC50 7.7 (IC50 2x10-8 M) [2]
mitogen-activated protein kinase 12 Hs Inhibitor Inhibition 7.5 pIC50 - 2
pIC50 7.5 (IC50 3x10-8 M) [2]
mitogen-activated protein kinase 13 Hs Inhibitor Inhibition 6.5 pIC50 - 2
pIC50 6.5 (IC50 3x10-7 M) [2]