Compound Detail

CHEMBL4755698

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C=CC(=O)N1CCC(Cn2cc(-c3ccc4c(c3)OCO4)c3c(N)ncnc32)CC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4755698
Phase	Preclinical
Structure Type	MOL
InChI Key	RMTJSBZCZKCYHB-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

405.5

MW (Da)

2.83

ALogP

HBA

HBD

95.5

PSA (Å²)

0.67

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H23N5O3
MW	405.46
Aromatic Rings	3
Heavy Atoms	30
NP-Likeness	-0.44

Activity Summary

IC50 26 meas. best 7.66

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase BTK CHEMBL5251	IC50	7.66	6.16	21.7	2
Cytochrome P450 1A2 CHEMBL3356	IC50	7.22	7.22	60.0	1
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	7.21	7.21	61.5	1
Tyrosine-protein kinase Yes CHEMBL2073	IC50	6.84	6.84	145.9	1
Nuclear receptor subfamily 4 group A member 3 CHEMBL1961792	IC50	6.68	6.68	210.6	1
Tyrosine-protein kinase Lyn CHEMBL3905	IC50	6.59	6.59	259.0	1
Tyrosine-protein kinase TXK CHEMBL4367	IC50	6.48	6.48	330.7	1
Tyrosine-protein kinase Blk CHEMBL2250	IC50	6.3	6.3	503.7	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.2	6.2	636.5	1
Proto-oncogene tyrosine-protein kinase receptor Ret CHEMBL2041	IC50	6.19	6.19	639.8	1
Tyrosine-protein kinase Fgr CHEMBL4454	IC50	6.18	6.18	657.4	1
Tyrosine-protein kinase Fyn CHEMBL1841	IC50	6.0	6.0	1007.8	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	6.0	6.0	1000.9	1
Tyrosine-protein kinase HCK CHEMBL3234	IC50	5.95	5.95	1111.6	1
Tyrosine-protein kinase FRK CHEMBL4223	IC50	5.95	5.95	1129.3	1
Cytochrome P450 3A4 CHEMBL340	IC50	5.5	5.5	3190.0	1
Cytochrome P450 2C9 CHEMBL3397	IC50	5.45	5.45	3540.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	4.96	4.96	11100.0	2
L02 CHEMBL4296457	IC50	4.5	4.5	31300.0	1
HEK293 CHEMBL614818	IC50	4.47	4.47	34200.0	1
THP-1 CHEMBL614245	IC50	4.41	4.41	38900.0	1
Cytochrome P450 2C19 CHEMBL3622	IC50	4.38	4.38	41660.0	1
Cytochrome P450 2D6 CHEMBL289	IC50	4.22	4.22	60100.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	2522.28	ng.hr.mL-1	Rattus norvegicus
AUC	1239.63	ng.hr.mL-1	Rattus norvegicus
CL	137.17	mL.min-1.kg-1	Rattus norvegicus
CL	45.83	mL.min-1.kg-1	Rattus norvegicus
CL	4.2	mL.min-1.g-1	Homo sapiens
CL	7.4	mL.min-1.g-1	Rattus norvegicus
CL	4.4	mL.min-1.g-1	Canis lupus familiaris
CL	5.4	mL.min-1.g-1	Mus musculus
CL	8.2	mL.min-1.g-1	Macaca mulatta
Cmax	7724.56	nM	Rattus norvegicus
Cmax	635.82	nM	Rattus norvegicus
F	49.15	%	Rattus norvegicus
F	49.15	%	Rattus norvegicus
Ka	0.000578	/nM/min	Homo sapiens
T1/2	5.18	hr	Rattus norvegicus
T1/2	7.04	hr	Rattus norvegicus
T1/2	5.5	hr	Homo sapiens
T1/2	3.122	hr	Rattus norvegicus
T1/2	5.25	hr	Canis lupus familiaris
T1/2	4.278	hr	Mus musculus
T1/2	2.817	hr	Macaca mulatta
T1/2	7.04	hr	Rattus norvegicus
Tmax	0.11	hr	Rattus norvegicus
Tmax	0.96	hr	Rattus norvegicus
Vd	1.21	L.kg-1	Rattus norvegicus
Vd	26.15	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase BTK	IC50	=	21.7	nM	7.66	Inhibition of BTK (unknown origin) using Poly(Glu4,Tyr1) as substrate in presenc...	33740548
Cytochrome P450 1A2	IC50	=	60.0	nM	7.22	Inhibition of human liver microsome CYP1A2 using phenacetin as substrate incubat...	29324347
Cytoplasmic tyrosine-protein kinase BMX	IC50	=	61.5	nM	7.21	Inhibition of BMX (unknown origin)	29324347
Tyrosine-protein kinase Yes	IC50	=	145.9	nM	6.84	Inhibition of recombinant human YES using biotinyl-beta Abeta-Abeta AYQAEENTYDEY...	29324347
Nuclear receptor subfamily 4 group A member 3	IC50	=	210.6	nM	6.68	Inhibition of Tec (unknown origin)	29324347
Tyrosine-protein kinase Lyn	IC50	=	259.0	nM	6.59	Inhibition of recombinant human LYN using biotinyl-beta Abeta-Abeta AKVEKIGEGTYG...	29324347
Tyrosine-protein kinase TXK	IC50	=	330.7	nM	6.48	Inhibition of TXK (unknown origin)	29324347
Tyrosine-protein kinase Blk	IC50	=	503.7	nM	6.3	Inhibition of BLK (unknown origin)	29324347
Tyrosine-protein kinase Lck	IC50	=	636.5	nM	6.2	Inhibition of recombinant human LCK using Ulight-Poly GAT[EAY(1:1:1)]n as substr...	29324347
Proto-oncogene tyrosine-protein kinase receptor Ret	IC50	=	639.8	nM	6.19	Inhibition of RET (unknown origin)	29324347
Tyrosine-protein kinase Fgr	IC50	=	657.4	nM	6.18	Inhibition of FGR (unknown origin)	29324347
Proto-oncogene tyrosine-protein kinase Src	IC50	=	1000.9	nM	6.0	Inhibition of recombinant human SRC using Ulight-Poly GAT[EAY(1:1:1)]n as substr...	29324347
Tyrosine-protein kinase Fyn	IC50	=	1007.8	nM	6.0	Inhibition of recombinant human FYN using biotinyl-beta Abeta-Abeta AYQAEENTYDEY...	29324347
Tyrosine-protein kinase FRK	IC50	=	1129.3	nM	5.95	Inhibition of FRK (unknown origin)	29324347
Tyrosine-protein kinase HCK	IC50	=	1111.6	nM	5.95	Inhibition of HCK (unknown origin)	29324347
Cytochrome P450 3A4	IC50	=	3190.0	nM	5.5	Inhibition of human liver microsome CYP3A4 using dextromethorphan as substrate i...	29324347
Cytochrome P450 2C9	IC50	=	3540.0	nM	5.45	Inhibition of human liver microsome CYP2C9 using tolbutamide as substrate incuba...	29324347
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	11100.0	nM	4.96	Inhibition of human ERG expressed in CHO cells by automated Q-patch clamp assay	29324347
Voltage-gated inwardly rectifying potassium channel KCNH2	IC50	=	11100.0	nM	4.96	Inhibition of human ERG	33740548
Tyrosine-protein kinase BTK	IC50	=	21700.0	nM	4.66	Inhibition of BTK (unknown origin) by caliper mobility shift assay	29324347

Literature References

PubMed	DOI	Target Context	# Activities
29324347	10.1016/j.ejmech.2017.12.079	ADMET	34
29324347	10.1016/j.ejmech.2017.12.079	Tyrosine-protein kinase BTK	14
29324347	10.1016/j.ejmech.2017.12.079	Unchecked	3
29324347	10.1016/j.ejmech.2017.12.079	Mus musculus	3
33740548	10.1016/j.ejmech.2021.113329	ADMET	2
29324347	10.1016/j.ejmech.2017.12.079	Voltage-gated inwardly rectifying potassium channel KCNH2	2
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 2C19	1
29324347	10.1016/j.ejmech.2017.12.079	Tyrosine-protein kinase Blk	1
29324347	10.1016/j.ejmech.2017.12.079	Tyrosine-protein kinase TXK	1
33740548	10.1016/j.ejmech.2021.113329	Voltage-gated inwardly rectifying potassium channel KCNH2	1
29324347	10.1016/j.ejmech.2017.12.079	Nuclear receptor subfamily 4 group A member 3	1
29324347	10.1016/j.ejmech.2017.12.079	Cytoplasmic tyrosine-protein kinase BMX	1
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 2E1	1
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 2D6	1
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 2C9	1
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 3A4	1
29324347	10.1016/j.ejmech.2017.12.079	Cytochrome P450 1A2	1
29324347	10.1016/j.ejmech.2017.12.079	L02	1
29324347	10.1016/j.ejmech.2017.12.079	THP-1	1
29324347	10.1016/j.ejmech.2017.12.079	HEK293	1

Data from ChEMBL 36 via Core Engine