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Compound Detail

CHEMBL253770

INDIRUBIN 2
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O=C1Nc2ccc(Br)cc2/C1=C1/Nc2ccccc2/C1=N\O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL253770
Name INDIRUBIN 2
Phase Preclinical
Structure Type MOL
InChI Key TYNCGTPANDPODX-WAVHTBQISA-N
13
Targets
23
Activities
2
Assay Types
0
PK Parameters
17
Publications
0
Known Names

Molecular Properties

356.2
MW (Da)
3.42
ALogP
4
HBA
3
HBD
73.7
PSA (Ų)
0.38
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C16H10BrN3O2
MW 356.18
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.01

Activity Summary

IC50 22 meas. best 8.3
EC50 1 meas. best 4.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glycogen synthase kinase-3 beta
CHEMBL262
 IC50 8.3 8.3 5.0 1
Unchecked
CHEMBL612545
 IC50 8.3 7.825 5.0 2
Glycogen synthase kinase-3
CHEMBL2095188
 IC50 7.8 7.8 16.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 7.55 7.55 28.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.3 5.418 500.0 5
Polyunsaturated fatty acid 5-lipoxygenase
CHEMBL215
 IC50 5.58 5.4367 2600.0 3
MCF7
CHEMBL387
 IC50 5.24 5.24 5800.0 1
LoVo
CHEMBL614721
 IC50 5.18 5.18 6600.0 1
HepG2
CHEMBL395
 IC50 5.16 5.16 6900.0 1
A549
CHEMBL392
 IC50 5.14 5.14 7200.0 1
SH-SY5Y
CHEMBL614910
 IC50 4.92 4.8 12000.0 4
SK-MEL-28
CHEMBL614919
 IC50 4.76 4.76 17300.0 1
HT-22
CHEMBL614316
 EC50 4.07 4.07 85800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 5.0 nM 8.3 Inhibition of GSK3 17399989
Glycogen synthase kinase-3 beta IC50 = 5.012 nM 8.3 Inhibition of GSK3beta (unknown origin) expressed in Sf9 cells using GS1 as subs... -
Glycogen synthase kinase-3 IC50 = 16.0 nM 7.8 Inhibition of porcine brain GSK3alpha/beta 16854069
Cyclin-dependent kinase 5/CDK5 activator 1 IC50 = 28.0 nM 7.55 Inhibition of mammalian CDK5/p25 16854069
Unchecked IC50 = 45.0 nM 7.35 Inhibition of starfish CDK1/cyclin B in presence of 15 uM ATP 16854069
NON-PROTEIN TARGET IC50 = 500.0 nM 6.3 Antiproliferative activity against apoptosis sensitive mouse B16F10 cells after ... 26883150
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 2600.0 nM 5.58 Inhibition of 5-LO in human neutrophils assessed as product formation by cell-in... 24697244
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 3300.0 nM 5.48 Inhibition of 5-LO in human neutrophils assessed as product formation by cell-in... 24697244
NON-PROTEIN TARGET IC50 = 3600.0 nM 5.44 Antiproliferative activity against apoptosis resistant human OE21 cells after 72... 26883150
Polyunsaturated fatty acid 5-lipoxygenase IC50 = 5600.0 nM 5.25 Inhibition of human recombinant 5-LO assessed as product formation by cell-free ... 24697244
MCF7 IC50 = 5800.0 nM 5.24 Antiproliferative activity against apoptosis sensitive human MCF7 cells after 72... 26883150
LoVo IC50 = 6600.0 nM 5.18 Antiproliferative activity against human LoVo cells after 72 hrs by MTT assay 26883150
NON-PROTEIN TARGET IC50 = 6800.0 nM 5.17 Antiproliferative activity against apoptosis sensitive human PC3 cells after 72 ... 26883150
HepG2 IC50 = 6900.0 nM 5.16 Cytotoxicity against human HepG2 cells assessed as cell growth inhibition after ... 28743492
A549 IC50 = 7200.0 nM 5.14 Antiproliferative activity against apoptosis resistant human A549 cells after 72... 26883150
NON-PROTEIN TARGET IC50 = 8000.0 nM 5.1 Antiproliferative activity against apoptosis resistant human U373 cells after 72... 26883150
NON-PROTEIN TARGET IC50 = 8400.0 nM 5.08 Antiproliferative activity against apoptosis sensitive human Hs683 cells after 7... 26883150
SH-SY5Y IC50 = 12000.0 nM 4.92 Survival of human SH-SY5Y cells after 48 hrs by MTS reduction assay 16854069
SH-SY5Y IC50 = 13000.0 nM 4.89 Death of human SH-SY5Y cells in absence of 20 uM Q-VD-OPh by MTS reduction assay 16854069
SK-MEL-28 IC50 = 17300.0 nM 4.76 Antiproliferative activity against apoptosis resistant human SK-MEL-28 cells aft... 26883150

Literature References

PubMed DOI Target Context # Activities
29122482 10.1016/j.bmcl.2017.10.069 HT-22 7
16854069 10.1021/jm060314i SH-SY5Y 6
26883150 10.1016/j.bmcl.2016.02.015 NON-PROTEIN TARGET 5
24697244 10.1021/jm401740w Polyunsaturated fatty acid 5-lipoxygenase 5
36846374 10.1039/d2md00370h Klebsiella pneumoniae 2
18824607 10.1128/aac.00903-08 ADMET 2
18824607 10.1128/aac.00903-08 Toxoplasma gondii 1
- 10.1007/s00044-007-9086-8 Glycogen synthase kinase-3 beta 1
17399989 10.1016/j.bmc.2007.03.048 Unchecked 1
16854069 10.1021/jm060314i Unchecked 1
26883150 10.1016/j.bmcl.2016.02.015 A549 1
26883150 10.1016/j.bmcl.2016.02.015 SK-MEL-28 1
26883150 10.1016/j.bmcl.2016.02.015 MCF7 1
26883150 10.1016/j.bmcl.2016.02.015 LoVo 1
28743492 10.1016/j.bmc.2017.07.009 HepG2 1
16854069 10.1021/jm060314i Cyclin-dependent kinase 5/CDK5 activator 1 1
16854069 10.1021/jm060314i Glycogen synthase kinase-3 1

Data from ChEMBL 36 via Core Engine