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Compound Detail

CHEMBL5276374

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C=CC(=O)N1CCC([C@@H]2CCNc3c(C(N)=O)c(-c4cc(OC)c(C)c(OC)c4)nn32)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5276374
Phase Preclinical
Structure Type MOL
InChI Key ZFDGMDVYMNWICG-KRWDZBQOSA-N
15
Targets
21
Activities
1
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

453.5
MW (Da)
2.76
ALogP
7
HBA
2
HBD
111.7
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H31N5O4
MW 453.54
Aromatic Rings 2
Heavy Atoms 33
NP-Likeness -0.38

Activity Summary

IC50 21 meas. best 8.96

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Tyrosine-protein kinase BTK
CHEMBL5251
 IC50 8.96 8.4033 1.1 3
Tyrosine-protein kinase TXK
CHEMBL4367
 IC50 8.47 8.47 3.4 1
Rec1
CHEMBL4483266
 IC50 7.98 7.98 10.4 1
Cytoplasmic tyrosine-protein kinase BMX
CHEMBL3834
 IC50 7.82 7.82 15.0 1
Serine/threonine-protein kinase NLK
CHEMBL5364
 IC50 7.39 7.39 41.0 1
Receptor tyrosine-protein kinase erbB-4
CHEMBL3009
 IC50 7.03 7.03 94.0 1
Tyrosine-protein kinase Tec
CHEMBL4246
 IC50 7.0 6.8833 99.0 3
Tyrosine-protein kinase Blk
CHEMBL2250
 IC50 6.77 6.77 169.0 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 6.73 6.73 185.0 1
Myosin-IIIb
CHEMBL5654
 IC50 6.67 6.67 215.0 1
Epidermal growth factor receptor
CHEMBL203
 IC50 6.21 6.21 621.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.8 4.525 15900.0 2
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.44 4.44 36300.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.43 4.43 37400.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.21 4.21 61500.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 964.0 ng.hr.mL-1 Rattus norvegicus
AUC 2645.0 ng.hr.mL-1 Canis lupus familiaris
CL 24.4 mL.min-1.kg-1 Rattus norvegicus
CL 6.89 mL.min-1.kg-1 Canis lupus familiaris
CL 123.0 mL.min-1.g-1 Homo sapiens
CL 51.1 mL.min-1.g-1 Canis lupus familiaris
CL 44.7 mL.min-1.g-1 Rattus norvegicus
CL 148.0 mL.min-1.g-1 Mus musculus
Cmax 1470.65 nM Rattus norvegicus
Cmax 2747.28 nM Canis lupus familiaris
F 26.4 % Rattus norvegicus
F 43.0 % Canis lupus familiaris
Fu 0.04 - Homo sapiens
Fu 0.176 - Canis lupus familiaris
Fu 0.134 - Rattus norvegicus
Fu 0.134 - Mus musculus
T1/2 0.6 hr Rattus norvegicus
T1/2 2.5 hr Canis lupus familiaris
Tmax 0.25 hr Rattus norvegicus
Tmax 0.42 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 = 1.1 nM 8.96 Inhibition of N-terminal His-tagged recombinant human BTK (393 to 659 residues) ... 36912866
Tyrosine-protein kinase TXK IC50 = 3.4 nM 8.47 Inhibition of human TXK preincubated for 1 hrs followed by substrate addition an... 36912866
Tyrosine-protein kinase BTK IC50 = 4.1 nM 8.39 Inhibition of human BTK preincubated with compound for 1 hrs followed by ATP/33P... 36912866
Rec1 IC50 = 10.4 nM 7.98 Antiproliferative activity against human REC1 cells assessed as reduction in cel... 36912866
Tyrosine-protein kinase BTK IC50 = 13.9 nM 7.86 Inhibition of BTK phosphorylation at Tyr 223 residue in human Ramos cell incubat... 36912866
Cytoplasmic tyrosine-protein kinase BMX IC50 = 15.0 nM 7.82 Inhibition of human BMX preincubated for 1 hrs followed by substrate addition an... 36912866
Serine/threonine-protein kinase NLK IC50 = 41.0 nM 7.39 Inhibition of human NLK preincubated with compound for 1 hrs followed by ATP/33P... 36912866
Receptor tyrosine-protein kinase erbB-4 IC50 = 94.0 nM 7.03 Inhibition of human ERBB4 preincubated for 1 hrs followed by substrate addition ... 36912866
Tyrosine-protein kinase Tec IC50 = 99.0 nM 7.0 Inhibition of TEC (unknown origin) preincubated for 1 hrs followed by substrate ... 36912866
Tyrosine-protein kinase Tec IC50 = 99.0 nM 7.0 Inhibition of human TEC preincubated for 1 hrs followed by substrate addition an... 36912866
Tyrosine-protein kinase Blk IC50 = 169.0 nM 6.77 Inhibition of human BLK preincubated for 1 hrs followed by substrate addition an... 36912866
Tyrosine-protein kinase JAK3 IC50 = 185.0 nM 6.73 Inhibition of human JAK3 preincubated for 1 hrs followed by substrate addition a... 36912866
Myosin-IIIb IC50 = 215.0 nM 6.67 Inhibition of human MYO3b preincubated with compound for 1 hrs followed by ATP/3... 36912866
Tyrosine-protein kinase Tec IC50 = 223.1 nM 6.65 Inhibition of FLAG-tagged TEC autophosphorylation in HEK293 cells incubated for ... 36912866
Epidermal growth factor receptor IC50 = 621.0 nM 6.21 Inhibition of EGFR (unknown origin) preincubated for 1 hrs followed by substrate... 36912866
Epidermal growth factor receptor IC50 = 621.0 nM 6.21 Inhibition of human EGFR preincubated for 1 hrs followed by substrate addition a... 36912866
Cytochrome P450 3A4 IC50 = 15900.0 nM 4.8 Inhibition of CYP3A4 in pooled human liver microsomes using midazolam as substra... 36912866
Cytochrome P450 2C8 IC50 = 36300.0 nM 4.44 Inhibition of CYP2C8 in pooled human liver microsomes using amodiaquine as subst... 36912866
Cytochrome P450 2C9 IC50 = 37400.0 nM 4.43 Inhibition of CYP2C9 in pooled human liver microsomes using diclofenac as substr... 36912866
Cytochrome P450 3A4 IC50 = 55800.0 nM 4.25 Inhibition of CYP3A4 in pooled human liver microsomes using testosterone as subs... 36912866

Literature References

PubMed DOI Target Context # Activities
36912866 10.1021/acs.jmedchem.2c01938 ADMET 29
36912866 10.1021/acs.jmedchem.2c01938 Unchecked 13
36912866 10.1021/acs.jmedchem.2c01938 Tyrosine-protein kinase BTK 12
36912866 10.1021/acs.jmedchem.2c01938 Rattus norvegicus 5
36912866 10.1021/acs.jmedchem.2c01938 Mus musculus 5
36912866 10.1021/acs.jmedchem.2c01938 Rec1 4
36912866 10.1021/acs.jmedchem.2c01938 Epidermal growth factor receptor 3
36912866 10.1021/acs.jmedchem.2c01938 Tyrosine-protein kinase Tec 3
36912866 10.1021/acs.jmedchem.2c01938 Cytochrome P450 3A4 2
36912866 10.1021/acs.jmedchem.2c01938 Serine/threonine-protein kinase NLK 1
36912866 10.1021/acs.jmedchem.2c01938 Cytochrome P450 2C8 1
36912866 10.1021/acs.jmedchem.2c01938 Cytochrome P450 2B6 1
36912866 10.1021/acs.jmedchem.2c01938 Receptor tyrosine-protein kinase erbB-4 1
36912866 10.1021/acs.jmedchem.2c01938 Cytoplasmic tyrosine-protein kinase BMX 1
36912866 10.1021/acs.jmedchem.2c01938 Tyrosine-protein kinase JAK3 1
36912866 10.1021/acs.jmedchem.2c01938 Tyrosine-protein kinase Blk 1
36912866 10.1021/acs.jmedchem.2c01938 Myosin-IIIb 1
36912866 10.1021/acs.jmedchem.2c01938 Tyrosine-protein kinase TXK 1
36912866 10.1021/acs.jmedchem.2c01938 HEK293 1
36912866 10.1021/acs.jmedchem.2c01938 Ramos 1

Data from ChEMBL 36 via Core Engine