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Compound Detail

CHEMBL1096380

PLINABULIN
🧪 Phase III
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🧪 Phase III
CC(C)(C)c1[nH]cnc1/C=c1\[nH]c(=O)/c(=C/c2ccccc2)[nH]c1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1096380
Name PLINABULIN
Phase Phase III
Structure Type MOL
InChI Key UNRCMCRRFYFGFX-TYPNBTCFSA-N

Known Names

NPI-2358 Plinabulin Plinabulina Plinabuline
27
Targets
78
Activities
4
Assay Types
10
PK Parameters
20
Publications
4
Known Names
5
Indications
1
Mechanisms

Molecular Properties

336.4
MW (Da)
0.74
ALogP
3
HBA
3
HBD
94.4
PSA (Ų)
0.64
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -bulin; -nab-
USAN Year 2009

Extended Properties

Molecular Formula C19H20N4O2
MW 336.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness 0.24

Mechanism of Action

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

Indications

Carcinoma, Non-Small-Cell Lung Neutropenia Multiple Myeloma Small Cell Lung Carcinoma Neoplasms

Activity Summary

IC50 61 meas. best 8.48
EC50 9 meas. best 9.0
Kd 7 meas. best 6.0
Ki 1 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 9.0 8.05 1.0 9
Jurkat
CHEMBL397
 IC50 8.48 8.48 3.3 1
A549
CHEMBL392
 IC50 8.46 8.0425 3.5 4
BXPC-3
CHEMBL614530
 IC50 8.37 8.1167 4.3 3
HepG2
CHEMBL395
 IC50 8.32 8.32 4.8 1
U-937
CHEMBL612794
 IC50 8.22 8.195 6.0 2
HCT-116
CHEMBL394
 IC50 8.22 8.14 6.0 2
K562
CHEMBL385
 IC50 8.2 8.15 6.3 2
HT-29
CHEMBL384
 IC50 8.18 7.88 6.6 7
HeLa
CHEMBL399
 IC50 8.08 7.955 8.4 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.05 7.665 9.0 10
HL-60
CHEMBL383
 IC50 8.0 7.915 10.0 2
MCF7
CHEMBL387
 IC50 8.0 7.81 10.0 3
HUVEC
CHEMBL613979
 IC50 8.0 7.98 10.0 2
NCI-H1975
CHEMBL614348
 IC50 7.99 7.975 10.2 2
DU-145
CHEMBL613508
 IC50 7.85 7.85 14.0 1
NCI-H460
CHEMBL396
 IC50 7.58 7.535 26.2 4
NCI-H446
CHEMBL612440
 IC50 7.36 7.36 44.2 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 6.28 6.28 530.0 1
Tubulin
CHEMBL2111354
 Kd 6.0 5.9775 1000.0 4
Unchecked
CHEMBL612545
 Kd 6.0 6.0 1000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 5.91 5.91 1240.0 1
Unchecked
CHEMBL612545
 IC50 5.88 5.88 1310.0 1
Tubulin
CHEMBL2111354
 IC50 5.75 5.75 1800.0 1
Tubulin
CHEMBL2094134
 IC50 5.62 5.62 2400.0 1
Tubulin
CHEMBL2094134
 Ki 5.5 5.5 3200.0 1
Cytochrome P450 2C19
CHEMBL3622
 IC50 5.37 5.37 4230.0 1
Tubulin
CHEMBL2094134
 Kd 5.19 5.095 6400.0 2
Mitogen-activated protein kinase 10
CHEMBL4092
 IC50 5.17 5.17 6800.0 1
RAF proto-oncogene serine/threonine-protein kinase
CHEMBL1906
 IC50 5.05 5.05 8900.0 1
Cyclin-dependent kinase 1/cyclin B1
CHEMBL1907602
 IC50 5.0 5.0 10100.0 1
Tyrosine-protein kinase Lyn
CHEMBL2258
 IC50 4.96 4.96 11100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 720.76 ng.hr.mL-1 Rattus norvegicus
AUC 723.08 ng.hr.mL-1 Rattus norvegicus
CL 121.0 mL.min-1.kg-1 Rattus norvegicus
CL 23356.9 mL.min-1.g-1 Rattus norvegicus
Cmax 14976.22 nM Rattus norvegicus
MRT 0.5 hr Rattus norvegicus
T1/2 1.13 hr Rattus norvegicus
T1/2 0.989 hr Rattus norvegicus
Tmax 0.02 hr Rattus norvegicus
Vd 11.39 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET EC50 = 1.0 nM 9.0 Cytotoxicity against human PC3 cells assessed as reduction in cell viability mea... -
Jurkat IC50 = 3.3 nM 8.48 Cytotoxicity against human Jurkat cells assessed as decrease in cell viability a... 28228362
A549 IC50 = 3.5 nM 8.46 Cytotoxicity in human A549 cells assessed as reduction in cell viability incubat... 30910474
BXPC-3 IC50 = 4.28 nM 8.37 Antiproliferative activity against human BxPC3 cells after 72 hrs by sulforhodam... 29571653
HepG2 IC50 = 4.8 nM 8.32 Antiproliferative activity against human HepG2 cells assessed as reduction in ce... 31759826
A549 IC50 = 5.5 nM 8.26 Cytotoxicity against human A549 cells assessed as reduction in cell viability me... 27318124
BXPC-3 IC50 = 5.8 nM 8.24 Cytotoxicity against human BxPC3 cells assessed as reduction in cell viability i... 32278711
HCT-116 IC50 = 6.0 nM 8.22 Antiproliferative activity against human HCT116 cells assessed as reduction in c... 31759826
U-937 IC50 = 6.0 nM 8.22 Cytotoxicity against human U937 cells assessed as reduction in cell viability af... 24960627
K562 IC50 = 6.3 nM 8.2 Cytotoxicity against human K562 cells assessed as reduction in cell viability me... 27318124
NON-PROTEIN TARGET EC50 = 6.4 nM 8.19 Antiproliferative activity against human mitoxantrone-sensitive HL60 cells -
HT-29 IC50 = 6.6 nM 8.18 Cytotoxicity against human HT-29 cells assessed as reduction in cell viability a... 32278711
U-937 IC50 = 6.8 nM 8.17 Cytotoxicity against human U-937 cells assessed as reduction in cell viability m... 27318124
K562 IC50 = 8.0 nM 8.1 Cytotoxicity against human K562 cells assessed as reduction in cell viability af... 24960627
NON-PROTEIN TARGET EC50 = 8.17 nM 8.09 Antiproliferative activity against human mitoxantrone-resistant HL60/MX2 cells -
HeLa IC50 = 8.4 nM 8.08 Cytotoxicity against human HeLa cells assessed as reduction in cell viability me... 27318124
NON-PROTEIN TARGET EC50 = 8.5 nM 8.07 Antiproliferative activity against taxol-sensitive human MES-SA cells expressing... -
HCT-116 IC50 = 8.8 nM 8.06 Antiproliferative activity against human HCT-116 cells assessed as cell growth i... 37301522
NON-PROTEIN TARGET IC50 = 9.0 nM 8.05 Cytotoxicity against human BGC823 cells assessed as reduction in cell viability ... 24960627
HeLa IC50 = 9.0 nM 8.05 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 31759826

Literature References

PubMed DOI Target Context # Activities
30119994 10.1016/j.bmc.2018.08.009 ADMET 22
27318124 10.1016/j.ejmech.2016.06.002 U-937 11
30910474 10.1016/j.bmc.2019.03.035 A549 11
28228362 10.1016/j.bmcl.2017.01.096 Rattus norvegicus 9
22185476 10.1021/jm2009088 HeLa 9
30910474 10.1016/j.bmc.2019.03.035 NCI-H1975 7
22185476 10.1021/jm2009088 DU-145 4
25313318 10.1021/ml5001883 HeLa 3
22185476 10.1021/jm2009088 Unchecked 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 3
25313318 10.1021/ml5001883 Tubulin 2
28528081 10.1016/j.bmc.2017.04.024 Liver carboxylesterase 2
30910474 10.1016/j.bmc.2019.03.035 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
28228362 10.1016/j.bmcl.2017.01.096 Unchecked 2
24960627 10.1016/j.ejmech.2014.06.030 NON-PROTEIN TARGET 2
22185476 10.1021/jm2009088 HUVEC 2
37301522 10.1016/j.bmcl.2023.129370 Tubulin beta 2
22185476 10.1021/jm2009088 Mus musculus 1
21835627 10.1016/j.bmc.2011.07.017 HT-29 1

Data from ChEMBL 36 via Core Engine