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Compound Detail

CHEMBL430226

6-BROMOINDIRUBIN-3'-ACETOXIME
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CC(=O)O/N=C1C(=C2/C(=O)Nc3cc(Br)ccc32)/Nc2ccccc2/1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL430226
Name 6-BROMOINDIRUBIN-3'-ACETOXIME
Phase Preclinical
Structure Type MOL
InChI Key MENDIXKFTXYTHJ-HPBPSMLHSA-N
10
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

398.2
MW (Da)
3.51
ALogP
5
HBA
2
HBD
79.8
PSA (Ų)
0.44
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H12BrN3O3
MW 398.22
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.05

Activity Summary

IC50 17 meas. best 8.0
EC50 1 meas. best 6.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glycogen synthase kinase-3
CHEMBL2095188
 IC50 8.0 8.0 10.0 1
Aryl hydrocarbon receptor
CHEMBL3201
 EC50 6.8 6.8 160.0 1
A2058
CHEMBL613503
 IC50 6.44 6.44 361.0 1
Unchecked
CHEMBL612545
 IC50 6.22 5.6 605.0 8
M14
CHEMBL614317
 IC50 6.19 6.19 646.0 1
A-375
CHEMBL613859
 IC50 6.04 6.04 914.0 1
SK-MEL-2
CHEMBL614917
 IC50 6.03 6.03 942.0 1
CHL-1
CHEMBL1075422
 IC50 5.84 5.84 1458.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 5.62 5.62 2400.0 1
Cyclin-dependent kinase 1/cyclin B
CHEMBL2094127
 IC50 4.2 4.2 63000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glycogen synthase kinase-3 IC50 = 10.0 nM 8.0 Inhibitory activity against GSK-3-alpha/beta from porcine brain 14761195
Aryl hydrocarbon receptor EC50 = 160.0 nM 6.8 Agonist activity at human aryl hydrocarbon receptor 18077363
A2058 IC50 = 361.0 nM 6.44 Antiproliferative activity against human A2058 cells harboring BRAF V600E/PTEN n... 25915038
Unchecked IC50 = 605.0 nM 6.22 Antiproliferative activity against human MEXF462 cells harboring BRAF V600E muta... 25915038
M14 IC50 = 646.0 nM 6.19 Antiproliferative activity against human M14 cells harboring BRAF V600E mutation... 25915038
Unchecked IC50 = 750.0 nM 6.12 Antiproliferative activity against human MEL1102 cells harboring NRAS Q61K mutat... 25915038
A-375 IC50 = 914.0 nM 6.04 Antiproliferative activity against human A-375 cells harboring BRAF V600E mutati... 25915038
SK-MEL-2 IC50 = 942.0 nM 6.03 Antiproliferative activity against human SK-MEL-2 cells harboring NRAS Q61R muta... 25915038
Unchecked IC50 = 954.0 nM 6.02 Antiproliferative activity against human MEXF276 cells harboring BRAF V600E muta... 25915038
Unchecked IC50 = 1148.0 nM 5.94 Antiproliferative activity against human MEXF1341 cells harboring NRAS Q61 mutat... 25915038
CHL-1 IC50 = 1458.0 nM 5.84 Antiproliferative activity against human CHL-1 cells assessed as reduction in ce... 25915038
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 2400.0 nM 5.62 Inhibitory activity against Cyclin-dependent kinase 5-p35nck5a 14761195
Unchecked IC50 = 2400.0 nM 5.62 Inhibition of Cdk5/p25 18077363
Unchecked IC50 = 4300.0 nM 5.37 Inhibition Cdk2/cyclin A 18077363
Unchecked IC50 = 4939.0 nM 5.31 Antiproliferative activity against human MEXF1792 cells harboring NRAS G13D muta... 25915038
Cyclin-dependent kinase 1/cyclin B IC50 = 63000.0 nM 4.2 Inhibitory activity against cyclin dependent kinase 1-cyclinB from starfish (Mar... 14761195
Unchecked IC50 = 63000.0 nM 4.2 Inhibition of Cdk2/cyclin B 18077363
Cyclin-dependent kinase 1/cyclin B IC50 = 63000.0 nM 4.2 Inhibition of CDK1/cyclinB 15559249

Literature References

PubMed DOI Target Context # Activities
25915038 10.1371/journal.pone.0125028 Unchecked 5
18077363 10.1073/pnas.0708800104 Unchecked 5
18077363 10.1073/pnas.0708800104 Serine/threonine-protein kinase 26 2
18077363 10.1073/pnas.0708800104 Ribosomal protein S6 kinase alpha-3 2
18824607 10.1128/aac.00903-08 ADMET 2
27726390 10.1021/acs.jnatprod.6b00285 KCL-22 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase type 1G 1
18077363 10.1073/pnas.0708800104 Cyclin-dependent kinase 6 1
18077363 10.1073/pnas.0708800104 Cyclin-dependent kinase 2 1
25915038 10.1371/journal.pone.0125028 CHL-1 1
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase type II subunit gamma 1
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase type II subunit delta 1
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase type II subunit beta 1
18077363 10.1073/pnas.0708800104 Calcium/calmodulin-dependent protein kinase type II subunit alpha 1
14761195 10.1021/jm031016d Cyclin-dependent kinase 1/cyclin B 1
18077363 10.1073/pnas.0708800104 5'-AMP-activated protein kinase catalytic subunit alpha-2 1
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
15559249 10.1016/j.tips.2004.07.006 Cyclin-dependent kinase 1/cyclin B 1
18077363 10.1073/pnas.0708800104 Aryl hydrocarbon receptor 1

Data from ChEMBL 36 via Core Engine