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Compound Detail

CHEMBL552462

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COc1ccc(Nc2nc(N)c(C(=O)c3ccc(OC)c(OC)c3)s2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL552462
Phase Preclinical
Structure Type MOL
InChI Key OWBQCPZBRPKYKE-UHFFFAOYSA-N
10
Targets
12
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

385.4
MW (Da)
3.73
ALogP
8
HBA
2
HBD
95.7
PSA (Ų)
0.60
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H19N3O4S
MW 385.45
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.06

Activity Summary

IC50 12 meas. best 8.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
CCRF-CEM
CHEMBL382
 IC50 8.0 8.0 10.0 1
HL-60
CHEMBL383
 IC50 7.66 7.66 22.0 1
Unchecked
CHEMBL612545
 IC50 7.64 6.595 23.0 2
Tubulin beta
CHEMBL3832942
 IC50 7.6 7.6 25.0 1
MOLT-4
CHEMBL614177
 IC50 7.43 7.43 37.0 1
L1210
CHEMBL386
 IC50 7.42 7.42 38.0 1
HeLa
CHEMBL399
 IC50 7.28 7.28 52.0 1
Sphingosine kinase 2
CHEMBL3023
 IC50 7.22 7.22 60.0 1
Sphingosine kinase 1
CHEMBL4394
 IC50 7.22 5.87 60.0 2
FM3A
CHEMBL614297
 IC50 7.15 7.15 71.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
CCRF-CEM IC50 = 10.0 nM 8.0 Antiproliferative activity against human CEM cells after 2 days by coulter count... 19663386
HL-60 IC50 = 22.0 nM 7.66 Cytotoxicity against human HL-60 cells assessed as reduction in cell viability a... 32736077
Unchecked IC50 = 23.0 nM 7.64 Cytotoxicity against human HL60/VCR cells assessed as reduction in cell viabilit... 32736077
Tubulin beta IC50 = 25.0 nM 7.6 Binding affinity to beta tubulin in HEK293 cells assessed as disruption of micro... 32736077
MOLT-4 IC50 = 37.0 nM 7.43 Antiproliferative activity against human MOLT4 cells after 2 days by coulter cou... 19663386
L1210 IC50 = 38.0 nM 7.42 Antiproliferative activity against mouse L1210 cells after 2 days by coulter cou... 19663386
HeLa IC50 = 52.0 nM 7.28 Antiproliferative activity against human HeLa cells after 2 days by coulter coun... 19663386
Sphingosine kinase 1 IC50 = 60.0 nM 7.22 Binding affinity to SphK1 in HEK293 cells assessed as direct target engagement i... 32736077
Sphingosine kinase 2 IC50 = 60.0 nM 7.22 Binding affinity to SphK2 in HEK293 cells assessed as direct target engagement i... 32736077
FM3A IC50 = 71.0 nM 7.15 Antiproliferative activity against mouse FM3A cells after 2 days by coulter coun... 19663386
Unchecked IC50 = 2800.0 nM 5.55 Inhibition of bovine brain tubulin polymerization by turbidimetry 19663386
Sphingosine kinase 1 IC50 = 30000.0 nM 4.52 Inhibition of recombinant His6x-tagged human SphK1 expressed in HEK293 cells ass... 32736077

Literature References

PubMed DOI Target Context # Activities
32736077 10.1016/j.bmcl.2020.127453 ADMET 10
32736077 10.1016/j.bmcl.2020.127453 Unchecked 9
32736077 10.1016/j.bmcl.2020.127453 Cyclin-dependent kinase 1 8
19663386 10.1021/jm9001692 HeLa 6
32736077 10.1016/j.bmcl.2020.127453 Sphingosine kinase 1/2 5
32736077 10.1016/j.bmcl.2020.127453 Sphingosine kinase 1 3
32736077 10.1016/j.bmcl.2020.127453 Sphingosine kinase 2 3
19663386 10.1021/jm9001692 Unchecked 2
19663386 10.1021/jm9001692 CCRF-CEM 1
32736077 10.1016/j.bmcl.2020.127453 Glycogen synthase kinase-3 beta 1
19663386 10.1021/jm9001692 MOLT-4 1
32736077 10.1016/j.bmcl.2020.127453 HL-60 1
19663386 10.1021/jm9001692 FM3A 1
32736077 10.1016/j.bmcl.2020.127453 ATP-dependent translocase ABCB1 1
32736077 10.1016/j.bmcl.2020.127453 Multidrug resistance-associated protein 1 1
32736077 10.1016/j.bmcl.2020.127453 Glycogen synthase kinase-3 alpha 1
32736077 10.1016/j.bmcl.2020.127453 Tyrosine-protein kinase JAK1 1
32736077 10.1016/j.bmcl.2020.127453 Non-receptor tyrosine-protein kinase TYK2 1
32736077 10.1016/j.bmcl.2020.127453 Tubulin 1
32736077 10.1016/j.bmcl.2020.127453 Tubulin beta 1

Data from ChEMBL 36 via Core Engine