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Compound Detail

CHEMBL49642

INDIBULIN
🧪 Phase II
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🧪 Phase II
O=C(Nc1ccncc1)C(=O)c1cn(Cc2ccc(Cl)cc2)c2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL49642
Name INDIBULIN
Phase Phase II
Structure Type MOL
InChI Key SOLIIYNRSAWTSQ-UHFFFAOYSA-N

Known Names

D-24851 Indibulin Indibulina Indibuline ZIO-301
22
Targets
37
Activities
2
Assay Types
0
PK Parameters
20
Publications
5
Known Names
3
Indications
1
Mechanisms

Molecular Properties

389.8
MW (Da)
4.56
ALogP
4
HBA
1
HBD
64.0
PSA (Ų)
0.40
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -bulin
USAN Year 2007

Extended Properties

Molecular Formula C22H16ClN3O2
MW 389.84
Aromatic Rings 4
Heavy Atoms 28
NP-Likeness -1.64

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin inhibitor INHIBITOR Tubulin ✓ ✓

Indications

Breast Neoplasms Neoplasms Neoplasms

Activity Summary

IC50 35 meas. best 7.48
EC50 2 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A2780
CHEMBL614004
 EC50 7.72 7.71 19.0 2
SK-BR-3
CHEMBL613834
 IC50 7.48 7.48 33.0 1
SK-OV-3
CHEMBL614925
 IC50 7.44 7.0833 36.0 3
T47D
CHEMBL614361
 IC50 7.4 7.4 40.0 1
PC-3
CHEMBL390
 IC50 7.4 6.9967 40.0 3
L1210
CHEMBL386
 IC50 7.36 7.36 44.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.36 7.33 44.0 2
HCT-116
CHEMBL394
 IC50 7.3 7.3 50.0 1
DU-145
CHEMBL613508
 IC50 7.3 7.025 50.0 2
HT-29
CHEMBL384
 IC50 7.14 7.14 72.0 2
MDA-MB-231
CHEMBL400
 IC50 7.13 7.13 74.0 2
Unchecked
CHEMBL612545
 IC50 7.11 6.4933 77.0 3
P388
CHEMBL389
 IC50 7.11 7.11 77.0 1
HeLa
CHEMBL399
 IC50 6.94 6.94 115.0 1
Tubulin
CHEMBL2094134
 IC50 6.6 6.6 250.0 1
Tubulin
CHEMBL2095182
 IC50 6.6 6.6 250.0 1
A549
CHEMBL392
 IC50 6.4 6.04 398.0 2
NUGC-3
CHEMBL614208
 IC50 6.28 6.28 524.0 1
HCT-15
CHEMBL612263
 IC50 6.25 6.25 560.0 1
MCF7
CHEMBL387
 IC50 5.96 5.615 1100.0 2
MCF7S
CHEMBL614328
 IC50 5.95 5.95 1134.0 1
MES-SA/Dx5
CHEMBL613827
 IC50 5.52 5.325 3018.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A2780 EC50 = 19.0 nM 7.72 Antiproliferative activity against human A2780 cells incubated for 72 hrs by ATP... 31047749
A2780 EC50 = 20.0 nM 7.7 Antiproliferative activity against D4-9-31 resistance human A2780 cells incubate... 31047749
SK-BR-3 IC50 = 33.0 nM 7.48 Growth inhibition of human SKBR3 cells after 48 hrs by MTT assay 22850214
SK-OV-3 IC50 = 36.0 nM 7.44 Cytotoxicity against multidrug resistance human SK-OV-3 cells assessed as cell g... 36970141
PC-3 IC50 = 40.0 nM 7.4 Cytotoxicity against human PC-3 cells assessed as cell growth inhibition 33132173
T47D IC50 = 40.0 nM 7.4 Cytotoxicity against human T47D cells assessed as cell growth inhibition 33132173
NON-PROTEIN TARGET IC50 = 44.0 nM 7.36 Cytotoxicity against human KB/HeLa cells after 48 hrs by XTT assay 19682911
L1210 IC50 = 44.0 nM 7.36 Cytotoxicity against mouse L1210 cells after 48 hrs by XTT assay 19682911
NON-PROTEIN TARGET IC50 = 50.0 nM 7.3 Cytotoxicity against human HL60/TX1000 cells after 72 hrs by MTT assay 18308566
HCT-116 IC50 = 50.0 nM 7.3 Cytotoxicity against human HCT-116 cells assessed as cell growth inhibition 33132173
DU-145 IC50 = 50.0 nM 7.3 Cytotoxicity against human DU-145 cells assessed as cell growth inhibition 33132173
PC-3 IC50 = 64.0 nM 7.19 Cytotoxicity against multidrug resistance human PC-3 cells assessed as cell grow... 36970141
HT-29 IC50 = 72.0 nM 7.14 Antiproliferative activity against human HT-29 cells 19743863
HT-29 IC50 = 72.0 nM 7.14 Cytotoxicity against multidrug resistance human HT-29 cells assessed as cell gro... 36970141
MDA-MB-231 IC50 = 74.0 nM 7.13 Antiproliferative activity against human MDA-MB-231 cells 19743863
MDA-MB-231 IC50 = 74.0 nM 7.13 Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell surviv... 28494255
Unchecked IC50 = 77.0 nM 7.11 Cytotoxicity against multidrug resistance human U87 cells assessed as cell growt... 36970141
P388 IC50 = 77.0 nM 7.11 In vitro anticancer activity against murine leukemic P388 cells 12699388
SK-OV-3 IC50 = 77.0 nM 7.11 Cytotoxicity against human SKOV3 cells after 48 hrs by XTT assay 19682911
HeLa IC50 = 115.0 nM 6.94 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 31753698

Literature References

PubMed DOI Target Context # Activities
28131777 10.1016/j.ejmech.2017.01.026 DU-145 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
12699388 10.1021/jm020471r Mus musculus 4
26580420 10.1021/acs.jmedchem.5b01312 No relevant target 3
26580420 10.1021/acs.jmedchem.5b01312 Tubulin 2
26580420 10.1021/acs.jmedchem.5b01312 NON-PROTEIN TARGET 2
12699388 10.1021/jm020471r MES-SA/Dx5 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
33132173 10.1016/j.bmcl.2020.127635 Paracentrotus lividus 2
28131777 10.1016/j.ejmech.2017.01.026 Unchecked 2
31047749 10.1016/j.bmcl.2019.04.035 A2780 2
19743863 10.1021/jm900476c MDA-MB-231 1
19682911 10.1016/j.bmc.2009.07.048 L1210 1
19682911 10.1016/j.bmc.2009.07.048 NON-PROTEIN TARGET 1
19743863 10.1021/jm900476c Unchecked 1
36970141 10.1039/d2md00442a Unchecked 1
12699388 10.1021/jm020471r P388 1
12699388 10.1021/jm020471r MCF7 1
12699388 10.1021/jm020471r HepG2 1

Data from ChEMBL 36 via Core Engine