Compound Detail

CHEMBL103667

DORAMAPIMOD

🧪 Phase II

Enter ChEMBL ID:

Free Research Context This compound will appear in recent viewed items on the research home for this browser.

Research home View demo workspace

🧪 Phase II

Cc1ccc(-n2nc(C(C)(C)C)cc2NC(=O)Nc2ccc(OCCN3CCOCC3)c3ccccc23)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL103667
Name	DORAMAPIMOD
Phase	Phase II
Structure Type	MOL
InChI Key	MVCOAUNKQVWQHZ-UHFFFAOYSA-N

Known Names

BIRB 796 BS Birb-796 BIRB-796 BS Doramapimod

201

Targets

940

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

527.7

MW (Da)

5.99

ALogP

HBA

HBD

80.7

PSA (Å²)

0.31

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Achiral

Flags

Natural Product

USAN Stem	-imod
USAN Year	2002

Extended Properties

Molecular Formula	C31H37N5O3
MW	527.67
Aromatic Rings	4
Heavy Atoms	39
NP-Likeness	-1.81

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
MAP kinase p38 alpha inhibitor	INHIBITOR	Mitogen-activated protein kinase 14	✓	✓

Indications

Arthritis, Rheumatoid Psoriasis

Activity Summary

IC50 691 meas. best 10.0

Kd 223 meas. best 10.34

Ki 22 meas. best 10.01

EC50 4 meas. best 7.75

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Mitogen-activated protein kinase 14 CHEMBL2336	Kd	10.34	10.34	0.0	1
Mitogen-activated protein kinase 14 CHEMBL260	Kd	10.34	9.4933	0.0	15
MAP kinase p38 CHEMBL2094115	Kd	10.01	10.01	0.1	1
Mitogen-activated protein kinase 14 CHEMBL260	Ki	10.01	8.49	0.1	4
Mitogen-activated protein kinase 14 CHEMBL260	IC50	10.0	7.7185	0.1	20
Unchecked CHEMBL612545	Ki	10.0	10.0	0.1	1
Epithelial discoidin domain-containing receptor 1 CHEMBL5319	Kd	8.72	8.72	1.9	3
Mitogen-activated protein kinase 12 CHEMBL4674	Kd	8.54	8.0367	2.9	3
Mitogen-activated protein kinase 9 CHEMBL4179	Kd	8.34	8.2175	4.6	4
Mitogen-activated protein kinase 9 CHEMBL4179	IC50	8.22	7.5486	6.0	7
Unchecked CHEMBL612545	IC50	8.22	5.6756	6.0	9
Mitogen-activated protein kinase 9 CHEMBL4179	Ki	8.2	8.2	6.3	1
Mitogen-activated protein kinase 11 CHEMBL3961	IC50	8.15	8.15	7.0	1
Serine/threonine-protein kinase 10 CHEMBL3981	Kd	8.15	7.9967	7.1	3
Mitogen-activated protein kinase 11 CHEMBL3961	Kd	8.14	6.8733	7.2	3
MAP kinase p38 CHEMBL2094115	IC50	8.1	8.075	8.0	2
Tyrosine-protein kinase receptor Tie-1 CHEMBL5274	Kd	8.08	8.08	8.3	2
TRAF2 and NCK-interacting protein kinase CHEMBL4527	Kd	8.0	7.1375	9.9	4
Discoidin domain-containing receptor 2 CHEMBL5122	IC50	8.0	7.7033	10.0	3
Angiopoietin-1 receptor CHEMBL4128	Kd	7.96	7.7867	11.0	3
THP-1 CHEMBL614245	IC50	7.89	7.785	13.0	4
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.82	7.02	15.0	2
PBMC CHEMBL613107	IC50	7.82	7.67	15.0	2
Tumor necrosis factor CHEMBL1825	EC50	7.75	6.93	18.0	2
MAP kinase p38 CHEMBL2094115	EC50	7.75	7.75	18.0	1
Discoidin domain-containing receptor 2 CHEMBL5122	Kd	7.68	7.52	21.0	5
Angiopoietin-1 receptor CHEMBL4128	IC50	7.6	7.6	25.0	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	7.52	7.52	30.0	1
Mitogen-activated protein kinase 12 CHEMBL4674	IC50	7.52	6.82	30.0	5
Mitogen-activated protein kinase 10 CHEMBL2637	Ki	7.4	7.4	39.8	1
Misshapen-like kinase 1 CHEMBL5518	IC50	7.4	7.4	40.0	1
Tyrosine-protein kinase ABL1 CHEMBL1862	Kd	7.39	5.8883	41.0	18
Mitogen-activated protein kinase 13 CHEMBL2939	Ki	7.3	7.3	50.1	1
BDNF/NT-3 growth factors receptor CHEMBL4898	IC50	7.3	7.3	50.0	1
Heat shock protein beta-1 CHEMBL5976	IC50	7.24	7.24	58.0	1
Serine/threonine-protein kinase B-raf CHEMBL5145	IC50	7.22	7.15	60.0	2
Mitogen-activated protein kinase 10 CHEMBL2637	Kd	7.21	7.085	62.0	4
Ephrin type-A receptor 4 CHEMBL3988	IC50	7.16	7.16	70.0	1
Mitogen-activated protein kinase 13 CHEMBL2939	Kd	7.11	7.11	78.0	1
STE20-like serine/threonine-protein kinase CHEMBL4202	Kd	7.07	6.9033	86.0	3
Ephrin type-A receptor 5 CHEMBL3987	IC50	7.05	7.05	90.0	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Kd	7.05	7.05	90.0	2
Ephrin type-B receptor 1 CHEMBL5072	IC50	6.96	6.96	110.0	1
Ephrin type-A receptor 8 CHEMBL4134	Kd	6.85	6.6633	140.0	3
Mitogen-activated protein kinase kinase kinase 7 CHEMBL5776	Kd	6.82	6.82	150.0	1
Ephrin type-A receptor 2 CHEMBL2068	IC50	6.8	6.8	160.0	1
High affinity nerve growth factor receptor CHEMBL2815	IC50	6.8	6.8	160.0	1
Ephrin type-B receptor 2 CHEMBL3290	IC50	6.8	6.8	160.0	1
Cyclin-dependent kinase 8 CHEMBL5719	Ki	6.8	6.8	158.5	1
Mitogen-activated protein kinase kinase kinase kinase 4 CHEMBL6166	Ki	6.8	6.8	158.5	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	51000.0	-	Mus musculus
AUC	118000.0	-	Mus musculus
AUC	1150.0	-	Macaca fascicularis
AUC	10000.0	-	Macaca fascicularis
CL	0.33	mL.min-1.kg-1	Mus musculus
CL	14.4	mL.min-1.kg-1	Macaca fascicularis
CL	1.7	mL.min-1.kg-1	Rattus norvegicus
CL	42.66	uL.min-1.(10^6cells)-1	Homo sapiens
CL	69.18	uL.min-1.(10^6cells)-1	Rattus norvegicus
CL	124.0	mL.min-1.g-1	Homo sapiens
Cmax	51168.34	nM	Mus musculus
Cmax	3221.71	nM	Macaca fascicularis
Cmax	20656.85	nM	Rattus norvegicus
F	23.0	%	Mus musculus
F	80.0	%	Macaca fascicularis
F	76.0	%	Rattus norvegicus
Ka	1.21	10'4/M.s	Homo sapiens
T1/2	2.6	hr	Mus musculus
T1/2	1.6	hr	Macaca fascicularis
T1/2	24.0	hr	-
T1/2	3.85	hr	-
T1/2	19.25	hr	Homo sapiens
Tmax	1.0	hr	Mus musculus
Tmax	3.0	hr	Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Mitogen-activated protein kinase 14	Kd	=	0.046	nM	10.34	Kd value and murine Mitogen-activated protein kinase p38 alpha complex was calcu...	14561087
Mitogen-activated protein kinase 14	Kd	=	0.046	nM	10.34	Dissociation constant at Tref against human Mitogen-activated protein kinase p38...	14561086
Mitogen-activated protein kinase 14	Ki	=	0.097	nM	10.01	Inhibition of p38alpha	15975507
Mitogen-activated protein kinase 14	Kd	=	0.098	nM	10.01	Binding affinity to full-length GST-tagged p38alpha by surface plasmon resonance...	20471255
Mitogen-activated protein kinase 14	Kd	=	0.098	nM	10.01	Binding affinity for Mitogen-activated protein kinase p38 alpha	12941343
MAP kinase p38	Kd	=	0.097	nM	10.01	Binding affinity against human Mitogen-activated protein kinase p38 kinase evalu...	12086485
Unchecked	Ki	=	0.1	nM	10.0	Inhibition of p38V kinase stie 3 delta 296-301 mutant	16783341
Mitogen-activated protein kinase 14	IC50	=	0.1	nM	10.0	Inhibition of p38alpha (unknown origin)	29620890
Mitogen-activated protein kinase 14	Kd	=	0.1	nM	10.0	Inhibition of SKF-86002 binding to human inactive p38alpha after 60 mins by fluo...	-
Mitogen-activated protein kinase 14	Kd	=	0.1	nM	10.0	Binding affinity to p38alpha by exchange curve binding kinetic analysis	19356929
Mitogen-activated protein kinase 14	Kd	=	0.1	nM	10.0	Dissociation constant at Tm against human Mitogen-activated protein kinase p38 a...	14561086
Mitogen-activated protein kinase 14	Kd	=	0.123	nM	9.91	Binding affinity to wild type human biotin labelled p38 alpha (9 to 352 residues...	28834431
Mitogen-activated protein kinase 14	Kd	=	0.16	nM	9.8	Inhibition of p38alpha	20655210
Mitogen-activated protein kinase 14	Kd	=	0.24	nM	9.62	Average Binding Constant for p38-alpha; NA=Not Active at 10 uM	15711537
Mitogen-activated protein kinase 14	Kd	=	0.37	nM	9.43	Binding constant for full-length p38-alpha	18183025
Mitogen-activated protein kinase 14	Kd	=	0.45	nM	9.35	Binding constant for p38-alpha kinase domain	22037378
Mitogen-activated protein kinase 14	Kd	=	1.0	nM	9.0	Binding affinity to p38alpha MAPK by surface plasmon resonance method	21888439
Mitogen-activated protein kinase 14	Kd	=	1.3	nM	8.89	Dissociation constant at Tm against human Mitogen-activated protein kinase p38 a...	14561086
Epithelial discoidin domain-containing receptor 1	Kd	=	1.9	nM	8.72	Binding constant for DDR1 kinase domain	18183025
Epithelial discoidin domain-containing receptor 1	Kd	=	1.9	nM	8.72	Binding affinity to DDR1 (unknown origin)	25569119

Literature References

PubMed	DOI	Target Context	# Activities
22037378	10.1038/nbt.1990	Tyrosine-protein kinase ABL1	15
22037378	10.1038/nbt.1990	Epidermal growth factor receptor	12
18183025	10.1038/nbt1358	Epidermal growth factor receptor	10
22037378	10.1038/nbt.1990	Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform	10
26254279	10.18632/oncotarget.4214	Unchecked	9
22037378	10.1038/nbt.1990	Mast/stem cell growth factor receptor Kit	8
12086485	10.1021/jm020057r	Cynomolgus monkey	8
12086485	10.1021/jm020057r	Mus musculus	8
-	10.6019/CHEMBL5303304	HEK-293T	7
15711537	10.1038/nbt1068	Tyrosine-protein kinase ABL1	7
22037378	10.1038/nbt.1990	Receptor-type tyrosine-protein kinase FLT3	7
18183025	10.1038/nbt1358	Tyrosine-protein kinase ABL1	7
28834431	10.1021/acs.jmedchem.7b00745	Mitogen-activated protein kinase 14	7
18183025	10.1038/nbt1358	Receptor-type tyrosine-protein kinase FLT3	5
18183025	10.1038/nbt1358	Mast/stem cell growth factor receptor Kit	5
19244237	10.1074/jbc.m809038200	Protein-tyrosine kinase 2-beta	5
17095218	10.1016/j.bmcl.2006.10.044	No relevant target	4
22749282	10.1016/j.bmcl.2012.05.095	Mus musculus	4
18602262	10.1016/j.bmcl.2008.06.028	Mitogen-activated protein kinase 14	4
22037378	10.1038/nbt.1990	Proto-oncogene tyrosine-protein kinase receptor Ret	4

Data from ChEMBL 36 via Core Engine