Compound Detail

CHEMBL4851021

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C=CC(=O)N1CC[C@@H](NC(=O)c2sc3nccc4c3c2NC(=O)N4c2ccc(Oc3ccccc3)cc2C)C1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL4851021
Phase	Preclinical
Structure Type	MOL
InChI Key	VXJXHNMYRAHBBO-GOSISDBHSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

539.6

MW (Da)

5.60

ALogP

HBA

HBD

103.9

PSA (Å²)

0.31

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Unknown
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C29H25N5O4S
MW	539.62
Aromatic Rings	4
Heavy Atoms	39
NP-Likeness	-1.30

Activity Summary

IC50 22 meas. best 8.1

Ki 2 meas. best 7.54

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Tyrosine-protein kinase BTK CHEMBL5251	IC50	8.1	7.3811	7.9	9
Tyrosine-protein kinase BTK CHEMBL3259478	IC50	7.96	7.96	11.0	1
Unchecked CHEMBL612545	IC50	7.96	7.425	11.0	2
Tyrosine-protein kinase BTK CHEMBL5251	Ki	7.54	7.54	28.8	2
Blood CHEMBL613416	IC50	7.08	7.08	84.0	1
Tyrosine-protein kinase Lck CHEMBL258	IC50	6.89	6.89	130.0	1
Cytoplasmic tyrosine-protein kinase BMX CHEMBL3834	IC50	6.89	6.89	129.0	1
Blood CHEMBL613615	IC50	6.89	6.89	130.0	1
Receptor tyrosine-protein kinase erbB-4 CHEMBL3009	IC50	6.42	6.42	377.0	1
Tyrosine-protein kinase Tec CHEMBL4246	IC50	6.39	6.39	409.0	1
Tyrosine-protein kinase TXK CHEMBL4367	IC50	5.75	5.75	1770.0	1
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	5.46	5.46	3490.0	1
Tyrosine-protein kinase Fgr CHEMBL4454	IC50	5.32	5.32	4760.0	1
Serine/threonine-protein kinase B-raf CHEMBL5145	IC50	5.11	5.11	7840.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	39.6	mL.min-1.kg-1	Rattus norvegicus
CL	8.0	mL.min-1.kg-1	Canis lupus familiaris
Cmax	600.0	nM	Rattus norvegicus
Cmax	1500.0	nM	Canis lupus familiaris
F	29.7	%	Rattus norvegicus
F	68.0	%	Canis lupus familiaris
Fu	0.0016	-	Homo sapiens
Fu	0.0047	-	Rattus norvegicus
Fu	0.0012	-	Canis lupus familiaris
Fu	0.0025	-	Macaca fascicularis
T1/2	0.3	hr	Rattus norvegicus
T1/2	1.9	hr	Canis lupus familiaris
T1/2	0.3833	hr	Homo sapiens
Tmax	1.0	hr	Rattus norvegicus
Tmax	0.8	hr	Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Tyrosine-protein kinase BTK	IC50	=	7.94	nM	8.1	Kinase Lanthascreen Binding Assay: A BTK kinase lanthascreen binding assay monit...	-
Tyrosine-protein kinase BTK	IC50	=	7.94	nM	8.1	TBD: TBD	-
Tyrosine-protein kinase BTK	IC50	=	11.0	nM	7.96	Inhibition of BTK in C57Bl/6 mouse splenocyte assessed as reduction in anti-IgM-...	34055226
Unchecked	IC50	=	11.0	nM	7.96	Inhibition of anti-IgM-induced B cell activation in C57Bl/6 mouse splenocytes as...	36314537
Tyrosine-protein kinase BTK	IC50	=	12.6	nM	7.9	TBD: TBD	-
Tyrosine-protein kinase BTK	IC50	=	15.8	nM	7.8	TBD: TBD	-
Tyrosine-protein kinase BTK	IC50	=	15.8	nM	7.8	Kinase Lanthascreen Binding Assay: A BTK kinase lanthascreen binding assay monit...	-
Tyrosine-protein kinase BTK	Ki	=	28.8	nM	7.54	Inhibition of full length N-terminal GST-tagged human BTK expressed in Sf21 cell...	36314537
Tyrosine-protein kinase BTK	Ki	=	28.8	nM	7.54	Covalent inhibition of recombinant human GST-tagged BTK (2 to 659 end residues) ...	34055226
Blood	IC50	=	84.0	nM	7.08	Inhibition of anti-IgM-induced B cell activation in human whole blood assessed a...	36314537
Tyrosine-protein kinase BTK	IC50	=	84.0	nM	7.08	Inhibition of BTK in human whole blood assessed as inhibition of IgM-induced B-c...	34055226
Unchecked	IC50	=	130.0	nM	6.89	Inhibition of BTK in Wistar rat whole blood assessed as reduction in anti-IgD-in...	34055226
Cytoplasmic tyrosine-protein kinase BMX	IC50	=	129.0	nM	6.89	Inhibition of recombinant human full length BMX using poly(Glu, Tyr) 4:1 as subs...	34055226
Tyrosine-protein kinase Lck	IC50	=	130.0	nM	6.89	Inhibition of recombinant human full length LCK using KVEKIGEGTYGVVYK as substra...	34055226
Blood	IC50	=	130.0	nM	6.89	Inhibition of anti-IgD-induced B cell activation in Wistar rat whole blood asses...	36314537
Tyrosine-protein kinase BTK	IC50	=	142.0	nM	6.85	Inhibition of recombinant human BTK using KVEKIGEGTYGVVYK as substrate incubated...	34055226
Receptor tyrosine-protein kinase erbB-4	IC50	=	377.0	nM	6.42	Inhibition of recombinant human ERBB4 (706 to 991 residues) using poly(Glu, Tyr)...	34055226
Tyrosine-protein kinase BTK	IC50	=	398.0	nM	6.4	TBD: TBD	-
Tyrosine-protein kinase BTK	IC50	=	398.0	nM	6.4	Kinase Lanthascreen Binding Assay: A BTK kinase lanthascreen binding assay monit...	-
Tyrosine-protein kinase Tec	IC50	=	409.0	nM	6.39	Inhibition of recombinant human TEC (174 to end residues) using EFPIYDFLPAKKK as...	34055226

Literature References

PubMed	DOI	Target Context	# Activities
34055226	10.1021/acsmedchemlett.1c00044	ADMET	12
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase BTK	8
36314537	10.1021/acs.jmedchem.2c01026	No relevant target	5
36314537	10.1021/acs.jmedchem.2c01026	ADMET	5
34055226	10.1021/acsmedchemlett.1c00044	Unchecked	3
36314537	10.1021/acs.jmedchem.2c01026	Tyrosine-protein kinase BTK	3
36314537	10.1021/acs.jmedchem.2c01026	Blood	2
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase Lck	2
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase Fgr	1
34055226	10.1021/acsmedchemlett.1c00044	Serine/threonine-protein kinase B-raf	1
34055226	10.1021/acsmedchemlett.1c00044	Proto-oncogene tyrosine-protein kinase Src	1
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase HCK	1
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase TXK	1
34055226	10.1021/acsmedchemlett.1c00044	Rattus norvegicus	1
34055226	10.1021/acsmedchemlett.1c00044	Tyrosine-protein kinase Tec	1
34055226	10.1021/acsmedchemlett.1c00044	Receptor tyrosine-protein kinase erbB-4	1
36314537	10.1021/acs.jmedchem.2c01026	Unchecked	1
34055226	10.1021/acsmedchemlett.1c00044	Cytoplasmic tyrosine-protein kinase BMX	1

Data from ChEMBL 36 via Core Engine