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Compound Detail

CHEMBL4526274

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O=C(CCCCCn1cc(Nc2ncc(Cl)c(Nc3ccc(Cl)cc3)n2)cn1)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4526274
Phase Preclinical
Structure Type MOL
InChI Key MTOQNLGMTJOJOF-UHFFFAOYSA-N
12
Targets
12
Activities
1
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

450.3
MW (Da)
4.53
ALogP
8
HBA
4
HBD
117.0
PSA (Ų)
0.20
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H21Cl2N7O2
MW 450.33
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.64

Activity Summary

IC50 12 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase
CHEMBL2093865
 IC50 8.7 8.7 2.0 1
Tyrosine-protein kinase JAK2
CHEMBL2971
 IC50 8.4 8.4 4.0 1
Tyrosine-protein kinase JAK1
CHEMBL2835
 IC50 8.32 8.32 4.8 1
Tyrosine-protein kinase JAK3
CHEMBL2148
 IC50 8.13 8.13 7.4 1
Histone deacetylase 6
CHEMBL1865
 IC50 7.85 7.85 14.0 1
Non-receptor tyrosine-protein kinase TYK2
CHEMBL3553
 IC50 7.31 7.31 49.0 1
Jurkat
CHEMBL397
 IC50 7.22 7.22 60.0 1
MOLT-4
CHEMBL614177
 IC50 7.1 7.1 80.0 1
HEL
CHEMBL613888
 IC50 7.05 7.05 90.0 1
Histone deacetylase 2
CHEMBL1937
 IC50 6.92 6.92 120.0 1
K562
CHEMBL385
 IC50 6.31 6.31 490.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 5.61 5.61 2470.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 33.0 ng.hr.mL-1 Mus musculus
AUC 28.4 ng.hr.mL-1 Mus musculus
CL 160.9 mL.min-1.kg-1 Rattus norvegicus
CL 643.0 mL.min-1.kg-1 Mus musculus
Cmax 262.03 nM Mus musculus
F 1.0 % Rattus norvegicus
F 116.0 % Mus musculus
T1/2 0.32 hr Rattus norvegicus
T1/2 0.32 hr Mus musculus
T1/2 0.26 hr Mus musculus
T1/2 0.2433 hr Rattus norvegicus
T1/2 0.43 hr Homo sapiens
T1/2 0.6933 hr Rattus norvegicus
T1/2 6.018 hr Homo sapiens
Tmax 0.12 hr Mus musculus
Vd 18.4 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase IC50 = 2.0 nM 8.7 Inhibition of HDAC in human HeLa nuclear extract using Boc-Lys(acetyl)-AMC as su... 30901208
Tyrosine-protein kinase JAK2 IC50 = 4.0 nM 8.4 Inhibition of recombinant human JAK2 using Ulight-CAGAGAIETDKEYYTVKD as substrat... 30901208
Tyrosine-protein kinase JAK1 IC50 = 4.8 nM 8.32 Inhibition of recombinant human JAK1 using Ulight-CAGAGAIETDKEYYTVKD as substrat... 30901208
Tyrosine-protein kinase JAK3 IC50 = 7.4 nM 8.13 Inhibition of recombinant human JAK3 using Ulight-CAGAGAIETDKEYYTVKD as substrat... 30901208
Histone deacetylase 6 IC50 = 14.0 nM 7.85 Inhibition of HDAC6 (unknown origin) using Boc-Lys(acetyl)-AMC as substrate prei... 30901208
Non-receptor tyrosine-protein kinase TYK2 IC50 = 49.0 nM 7.31 Inhibition of recombinant human TYK2 using Ulight-CAGAGAIETDKEYYTVKD as substrat... 30901208
Jurkat IC50 = 60.0 nM 7.22 Antiproliferative activity against human Jurkat cells assessed as reduction in c... 30901208
MOLT-4 IC50 = 80.0 nM 7.1 Antiproliferative activity against human MOLT4 cells assessed as reduction in ce... 30901208
HEL IC50 = 90.0 nM 7.05 Antiproliferative activity against HEL cells harboring JAK2 V617F mutant assesse... 30901208
Histone deacetylase 2 IC50 = 120.0 nM 6.92 Inhibition of HDAC2 (unknown origin) using Boc-Lys(acetyl)-AMC as substrate prei... 30901208
K562 IC50 = 490.0 nM 6.31 Antiproliferative activity against human K562 cells assessed as reduction in cel... 30901208
Histone deacetylase 8 IC50 = 2470.0 nM 5.61 Inhibition of HDAC8 (unknown origin) using Boc-Lys(trifluoroacetyl)-AMC as subst... 30901208

Literature References

PubMed DOI Target Context # Activities
30901208 10.1021/acs.jmedchem.8b01597 ADMET 22
30901208 10.1021/acs.jmedchem.8b01597 HEL 10
30901208 10.1021/acs.jmedchem.8b01597 K562 9
30901208 10.1021/acs.jmedchem.8b01597 Unchecked 4
30901208 10.1021/acs.jmedchem.8b01597 Non-receptor tyrosine-protein kinase TYK2 3
30901208 10.1021/acs.jmedchem.8b01597 Tyrosine-protein kinase JAK2 3
30901208 10.1021/acs.jmedchem.8b01597 Mast/stem cell growth factor receptor Kit 2
30901208 10.1021/acs.jmedchem.8b01597 Tyrosine-protein kinase receptor UFO 2
30901208 10.1021/acs.jmedchem.8b01597 Tyrosine-protein kinase ABL2 2
30901208 10.1021/acs.jmedchem.8b01597 Activin receptor type-1B 2
30901208 10.1021/acs.jmedchem.8b01597 RAC-alpha serine/threonine-protein kinase 2
30901208 10.1021/acs.jmedchem.8b01597 ALK tyrosine kinase receptor 2
30901208 10.1021/acs.jmedchem.8b01597 Tyrosine-protein kinase ABL1 2
30901208 10.1021/acs.jmedchem.8b01597 Protein-tyrosine kinase 6 2
30901208 10.1021/acs.jmedchem.8b01597 Serine/threonine-protein kinase Chk1 2
30901208 10.1021/acs.jmedchem.8b01597 Serine/threonine-protein kinase BRSK1 2
30901208 10.1021/acs.jmedchem.8b01597 Histone deacetylase 6 2
30901208 10.1021/acs.jmedchem.8b01597 Cyclin-dependent kinase 6 2
30901208 10.1021/acs.jmedchem.8b01597 Tyrosine-protein kinase SYK 2
30901208 10.1021/acs.jmedchem.8b01597 Calcium/calmodulin-dependent protein kinase type 1 2

Data from ChEMBL 36 via Core Engine