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Compound Detail

CHEMBL3590106

ULIXERTINIB
🧪 Phase II
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🧪 Phase II
CC(C)Nc1cc(-c2c[nH]c(C(=O)N[C@H](CO)c3cccc(Cl)c3)c2)c(Cl)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3590106
Name ULIXERTINIB
Phase Phase II
Structure Type MOL
InChI Key KSERXGMCDHOLSS-LJQANCHMSA-N

Known Names

Bvd-523 BVD-ERK Ulixertinib VRT-752271
13
Targets
26
Activities
3
Assay Types
8
PK Parameters
20
Publications
4
Known Names
6
Indications
2
Mechanisms

Molecular Properties

433.3
MW (Da)
4.67
ALogP
4
HBA
4
HBD
90.0
PSA (Ų)
0.44
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -tinib

Extended Properties

Molecular Formula C21H22Cl2N4O2
MW 433.34
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.08

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
MAP kinase ERK1 inhibitor INHIBITOR Mitogen-activated protein kinase 3 ✓ ✓
MAP kinase ERK2 inhibitor INHIBITOR Mitogen-activated protein kinase 1 ✓ ✓

Indications

Neoplasms Uveal Melanoma Leukemia, Myeloid, Acute Myelodysplastic Syndromes Pancreatic Neoplasms Paraganglioma

Activity Summary

IC50 19 meas. best 10.52
Kd 6 meas. best 9.5
Ki 1 meas. best 10.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 10.52 7.356 0.0 5
Mitogen-activated protein kinase 1
CHEMBL4040
 Ki 10.4 10.4 0.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
 Kd 9.5 8.08 0.3 3
COLO 205
CHEMBL614561
 IC50 6.99 6.99 102.7 1
Mitogen-activated protein kinase; ERK1/ERK2
CHEMBL1907606
 IC50 6.85 6.3933 140.0 3
Mitogen-activated protein kinase 3
CHEMBL3385
 Kd 6.8 6.8 160.0 1
A-375
CHEMBL613859
 IC50 6.75 6.75 180.0 1
Unchecked
CHEMBL612545
 IC50 6.52 6.215 300.0 2
SK-CO-1
CHEMBL1075576
 IC50 6.45 6.45 356.0 1
Serine/threonine-protein kinase TAO1
CHEMBL5261
 Kd 6.41 6.41 388.0 1
BaF3
CHEMBL614524
 IC50 6.33 5.6833 468.0 3
SW-620
CHEMBL612262
 IC50 6.3 6.3 499.0 1
ASPC1
CHEMBL612588
 IC50 6.07 6.07 849.0 1
NCI-H23
CHEMBL614997
 IC50 6.0 6.0 1000.0 1
Serine/threonine-protein kinase D2
CHEMBL4900
 Kd 5.2 5.2 6336.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 113936.0 ng.hr.mL-1 Mus musculus
AUC 48848.0 ng.hr.mL-1 Mus musculus
Cmax 32.28 ug.mL-1 Mus musculus
Cmax 12.99 ug.mL-1 Mus musculus
Ka 7.5 10'-5/M/s Homo sapiens
Ka 1.3 10'-6/M/s Homo sapiens
T1/2 0.03333 hr Homo sapiens
T1/2 0.5833 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mitogen-activated protein kinase 1 IC50 = 0.03 nM 10.52 Inhibition of ERK2 (unknown origin) 26259804
Mitogen-activated protein kinase 1 Ki = 0.04 nM 10.4 Binding affinity to ERK2 (unknown origin) measured after 20 mins in presence of ... 36205714
Mitogen-activated protein kinase 1 Kd = 0.3162 nM 9.5 Binding affinity to MEK-activated phosphorylated biotinylated ERK2 (unknown orig... 31710489
Mitogen-activated protein kinase 1 Kd = 10.0 nM 8.0 Binding affinity to non-phosphorylated biotinylated ERK2 (unknown origin) by SPR... 31710489
Mitogen-activated protein kinase 1 IC50 = 10.6 nM 7.97 Inhibition of ERK2 (unknown origin) measured after 2 hr by ADP-glo assay 35450372
Mitogen-activated protein kinase 1 IC50 = 31.0 nM 7.51 Inhibition of ERK2 in human A375 cells harboring BRAF V600E mutant assessed as d... 28376306
COLO 205 IC50 = 102.7 nM 6.99 Antiproliferative activity against human COLO 205 cells assessed as reduction in... 35450372
Mitogen-activated protein kinase; ERK1/ERK2 IC50 = 140.0 nM 6.85 Inhibition of ERK1/2 in human A375 cells harboring B-RAF V600E mutant assessed a... 25977981
Mitogen-activated protein kinase; ERK1/ERK2 IC50 = 150.0 nM 6.82 Inhibition of ERK1/2 in human A375 cells assessed as inhibition of RSK phosphory... 31710489
Mitogen-activated protein kinase 3 Kd = 160.0 nM 6.8 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
A-375 IC50 = 180.0 nM 6.75 Antiproliferative activity against human A375 cells harboring B-RAF V600E mutant... 25977981
Mitogen-activated protein kinase 1 Kd = 183.0 nM 6.74 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
Unchecked IC50 = 300.0 nM 6.52 Inhibition of MAPK/ERK signaling pathway in human NCI-H1975 cells 38295689
SK-CO-1 IC50 = 356.0 nM 6.45 Antiproliferative activity against human SKCO1 cells harboring KRAS G12V mutant ... 28038940
Serine/threonine-protein kinase TAO1 Kd = 388.0 nM 6.41 Kinobeads (epsilon), multiple immobilized ATP-competitive broad spectrum kinase ... 29191878
BaF3 IC50 = 468.0 nM 6.33 Antiproliferative activity against mouse BA/F3 cells harboring KRAS G12D mutant ... 28038940
SW-620 IC50 = 499.0 nM 6.3 Antiproliferative activity against human SW620 cells harboring KRAS G12V mutant ... 28038940
ASPC1 IC50 = 849.0 nM 6.07 Antiproliferative activity against human AsPC1 cells harboring KRAS G12D mutant ... 28038940
NCI-H23 IC50 = 1000.0 nM 6.0 Antiproliferative activity against human NCI-H23 cells harboring KRAS G12C mutan... 28038940
Unchecked IC50 = 1240.0 nM 5.91 Antiproliferative activity against human SW156 cells harboring wild type KRAS af... 28038940

Literature References

PubMed DOI Target Context # Activities
31710489 10.1021/acs.jmedchem.9b01295 Mitogen-activated protein kinase 1 8
38613499 10.1021/acs.jmedchem.3c02392 Unchecked 7
35450372 10.1021/acsmedchemlett.2c00029 ADMET 5
29191878 10.1126/science.aan4368 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
28376306 10.1021/acs.jmedchem.7b00267 Mitogen-activated protein kinase 1 3
28038940 10.1016/j.bmc.2016.11.034 BaF3 3
25977981 10.1021/acs.jmedchem.5b00466 Mitogen-activated protein kinase 1 3
- 10.6019/CHEMBL5724709 U2OS 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
35450372 10.1021/acsmedchemlett.2c00029 COLO 205 2
- 10.6019/CHEMBL5724709 HEK-293T 2
28038940 10.1016/j.bmc.2016.11.034 Unchecked 2
31710489 10.1021/acs.jmedchem.9b01295 Mitogen-activated protein kinase; ERK1/ERK2 2
25977981 10.1021/acs.jmedchem.5b00466 No relevant target 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL5724709 Fibroblast 2
29191878 10.1126/science.aan4368 Acyl-CoA dehydrogenase family member 11 1
29191878 10.1126/science.aan4368 Acyl-CoA dehydrogenase family member 10 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1

Data from ChEMBL 36 via Core Engine