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Compound Detail

CHEMBL492399

VERUBULIN
🧪 Phase II
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🧪 Phase II
COc1ccc(N(C)c2nc(C)nc3ccccc23)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL492399
Name VERUBULIN
Phase Phase II
Structure Type MOL
InChI Key SNHCRNMVYDHVDT-UHFFFAOYSA-N

Known Names

Azixa MPC-6827 MX-128495 Verubulin Verubulina Verubuline
26
Targets
57
Activities
3
Assay Types
8
PK Parameters
20
Publications
6
Known Names
3
Indications
1
Mechanisms

Molecular Properties

279.3
MW (Da)
3.71
ALogP
4
HBA
0
HBD
38.2
PSA (Ų)
0.73
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -bulin
USAN Year 2010

Extended Properties

Molecular Formula C17H17N3O
MW 279.34
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -1.10

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin disrupting agent DISRUPTING AGENT Tubulin ✓ ✓

Indications

Glioblastoma Brain Neoplasms Neoplasms

Activity Summary

IC50 46 meas. best 9.15
EC50 10 meas. best 8.7
Kd 1 meas. best 4.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A-375
CHEMBL613859
 IC50 9.15 9.15 0.7 1
Unchecked
CHEMBL612545
 IC50 9.15 7.4313 0.7 8
A-431
CHEMBL614069
 IC50 9.05 9.05 0.9 1
M14
CHEMBL614317
 IC50 9.0 9.0 1.0 1
HeLa
CHEMBL399
 IC50 8.82 8.438 1.5 5
MDA-MB-435
CHEMBL614697
 IC50 8.77 8.77 1.7 1
SNU-398
CHEMBL614454
 EC50 8.7 8.7 2.0 1
T47D
CHEMBL614361
 EC50 8.7 8.7 2.0 5
Unchecked
CHEMBL612545
 EC50 8.68 8.68 2.1 1
SK-OV-3
CHEMBL614925
 IC50 8.66 8.58 2.2 3
Epidermal growth factor receptor
CHEMBL203
 IC50 8.55 8.55 2.8 1
U-251
CHEMBL615022
 IC50 8.55 8.55 2.8 1
RKO
CHEMBL614879
 IC50 8.52 8.41 3.0 2
A549
CHEMBL392
 IC50 8.52 8.4067 3.0 3
HCT-116
CHEMBL394
 EC50 8.52 8.52 3.0 1
HCT-116
CHEMBL394
 IC50 8.4 8.28 4.0 4
HepG2
CHEMBL395
 IC50 8.34 8.29 4.6 4
Platelet-derived growth factor receptor beta
CHEMBL1913
 IC50 8.25 8.25 5.6 1
NCI-H1299
CHEMBL612255
 EC50 8.22 8.185 6.0 2
MDA-MB-231
CHEMBL400
 IC50 8.1 8.1 8.0 2
MGC-803
CHEMBL3706566
 IC50 8.1 8.1 8.0 1
LoVo
CHEMBL614721
 IC50 8.1 8.1 8.0 1
Vascular endothelial growth factor receptor 2
CHEMBL279
 IC50 8.08 8.08 8.4 1
A549/CDDP
CHEMBL4483225
 IC50 8.05 8.05 9.0 1
MCF7
CHEMBL387
 IC50 7.96 7.96 11.0 1
L02
CHEMBL4296457
 IC50 7.89 7.89 13.0 1
BJ
CHEMBL614358
 IC50 7.82 7.82 15.0 1
Chorioallantoic membrane
CHEMBL2367390
 IC50 5.55 5.55 2800.0 1
Unchecked
CHEMBL612545
 Kd 4.32 4.32 48400.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 11459.0 ng/ml Mus musculus
AUC 686.0 ng/ml Mus musculus
CL 51.8 mL.min-1.g-1 Homo sapiens
CL 232.3 mL.min-1.g-1 Rattus norvegicus
CL 1231.0 mL.min-1.g-1 Mus musculus
T1/2 0.4 hr Homo sapiens
T1/2 0.2 hr Rattus norvegicus
T1/2 0.05 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 0.7 nM 9.15 Antiproliferative activity against human A375/TxR cells assessed as inhibition o... 34406768
A-375 IC50 = 0.7 nM 9.15 Antiproliferative activity against human A-375 cells assessed as inhibition of c... 34406768
A-431 IC50 = 0.9 nM 9.05 Cytotoxicity against human A-431 cells assessed as reduction in cell viability b... 33647840
M14 IC50 = 1.0 nM 9.0 Antiproliferative activity against human M14 cells assessed as inhibition of cel... 34406768
Unchecked IC50 = 1.2 nM 8.92 Antiproliferative activity against human LCC6MDR cells assessed as inhibition of... 34406768
Unchecked IC50 = 1.4 nM 8.85 Antiproliferative activity against human MDA-MB-231/TxR cells assessed as inhibi... 34406768
HeLa IC50 = 1.5 nM 8.82 Cytotoxicity against human HeLa cells over expressing WT-beta3 assessed as reduc... 33647840
MDA-MB-435 IC50 = 1.7 nM 8.77 Antiproliferative activity against human MDA-MB-435 cells assessed as reduction ... 33647840
HeLa IC50 = 2.0 nM 8.7 Cytotoxicity against human HeLa cells assessed as reduction in cell viability by... 33647840
T47D EC50 = 2.0 nM 8.7 Induction of apoptosis in human T47D cells assessed as caspase cascade activatio... -
T47D EC50 = 2.0 nM 8.7 Induction of apoptosis in human T47D cells assessed as caspase cascade activatio... -
T47D EC50 = 2.0 nM 8.7 Induction of apoptosis in human T47D cells assessed as caspase activation 20188546
T47D EC50 = 2.0 nM 8.7 Induction of apoptosis in human T47D cells assessed as caspase activation after ... 19464890
T47D EC50 = 2.0 nM 8.7 Induction of apoptosis in human T47D cells assessed as caspase activation after ... 19296653
SNU-398 EC50 = 2.0 nM 8.7 Induction of apoptosis in human SNU398 cells assessed as caspase activation afte... 19296653
Unchecked EC50 = 2.1 nM 8.68 Induction of microtubule depolymerization in rat A10 cells incubated for over ni... 33647840
SK-OV-3 IC50 = 2.2 nM 8.66 Cytotoxicity against human SK-OV-3 cells assessed as reduction in cell viability... 33647840
SK-OV-3 IC50 = 2.6 nM 8.59 Cytotoxicity against human SK-OV-3 cells over expressing MDR1-6/6 assessed as re... 33647840
Epidermal growth factor receptor IC50 = 2.8 nM 8.55 Inhibition of EGFR in human A431 cells preincubated for 60 mins followed by EGF ... 33647840
U-251 IC50 = 2.8 nM 8.55 Cytotoxicity against human U-251 cells assessed as reduction in cell viability b... 33647840

Literature References

PubMed DOI Target Context # Activities
19296653 10.1021/jm801315b T47D 10
29509413 10.1021/acs.jmedchem.8b00128 Unchecked 9
34406768 10.1021/acs.jmedchem.1c01202 ADMET 6
27213819 10.1021/acs.jmedchem.6b00158 ADMET 4
34406768 10.1021/acs.jmedchem.1c01202 Unchecked 4
33647840 10.1016/j.bmc.2021.116061 Unchecked 4
33647840 10.1016/j.bmc.2021.116061 Platelet-derived growth factor receptor beta 3
19296653 10.1021/jm801315b MX1 3
33647840 10.1016/j.bmc.2021.116061 Vascular endothelial growth factor receptor 2 3
20188546 10.1016/j.bmcl.2010.01.155 T47D 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
29509413 10.1021/acs.jmedchem.8b00128 A549 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
33647840 10.1016/j.bmc.2021.116061 SK-OV-3 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
33647840 10.1016/j.bmc.2021.116061 Chorioallantoic membrane 2
33647840 10.1016/j.bmc.2021.116061 HeLa 2
33647840 10.1016/j.bmc.2021.116061 Epidermal growth factor receptor 2
19296653 10.1021/jm801315b Jurkat 2
19296653 10.1021/jm801315b SNU-398 2

Data from ChEMBL 36 via Core Engine