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Compound Detail

CHEMBL2393130

APABETALONE
🧪 Phase III
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🧪 Phase III
COc1cc(OC)c2c(=O)[nH]c(-c3cc(C)c(OCCO)c(C)c3)nc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2393130
Name APABETALONE
Phase Phase III
Structure Type MOL
InChI Key NETXMUIMUZJUTB-UHFFFAOYSA-N

Known Names

Apabetalona Apabetalone RVX-000222 RVX-208 RVX000222
17
Targets
126
Activities
4
Assay Types
1
PK Parameters
20
Publications
5
Known Names
6
Indications
1
Mechanisms

Molecular Properties

370.4
MW (Da)
2.60
ALogP
6
HBA
2
HBD
93.7
PSA (Ų)
0.69
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2016

Extended Properties

Molecular Formula C20H22N2O5
MW 370.41
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bromodomain and extra-terminal motif (BET) inhibitor INHIBITOR Bromodomain and extra-terminal motif (BET) ✓ ✓

Indications

Coronary Disease Diabetes Mellitus Hypertension, Pulmonary Severe Acute Respiratory Syndrome Fabry Disease Kidney Failure, Chronic

Activity Summary

IC50 75 meas. best 7.4
Kd 48 meas. best 6.89
Ki 2 meas. best 6.87
EC50 1 meas. best 5.17

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.4 6.094 40.0 30
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 6.89 6.3128 130.0 29
Bromodomain-containing protein 4
CHEMBL1163125
 Ki 6.87 6.405 135.0 2
Bromodomain-containing protein 3
CHEMBL1795186
 Kd 6.72 5.9586 190.0 7
Bromodomain-containing protein 2
CHEMBL1293289
 Kd 6.69 5.882 206.0 10
Bromodomain-containing protein 3
CHEMBL1795186
 IC50 6.69 5.7942 203.0 12
Bromodomain-containing protein 2
CHEMBL1293289
 IC50 6.61 5.9217 246.0 6
Bromodomain testis-specific protein
CHEMBL1795185
 IC50 6.16 5.7333 696.0 6
Bromodomain testis-specific protein
CHEMBL1795185
 Kd 6.15 5.735 708.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 5.77 5.77 1689.0 1
Unchecked
CHEMBL612545
 IC50 5.76 4.9 1730.0 4
MV4-11
CHEMBL613835
 IC50 5.35 5.35 4480.0 1
MOLM-14
CHEMBL3706570
 EC50 5.17 5.17 6700.0 1
SK-OV-3
CHEMBL614925
 IC50 5.15 5.15 7050.0 1
OCI-AML-3
CHEMBL4296479
 IC50 5.14 5.14 7170.0 1
ES-2
CHEMBL5058622
 IC50 5.1 5.1 8010.0 1
OCI-AML2
CHEMBL2366220
 IC50 5.08 5.08 8310.0 1
SW626
CHEMBL1075593
 IC50 5.07 5.07 8450.0 1
HCT-116
CHEMBL394
 IC50 4.89 4.89 12830.0 1
OVCAR-3
CHEMBL614213
 IC50 4.77 4.77 16890.0 1
NRK-49F
CHEMBL614203
 IC50 4.38 4.38 42000.0 1
A549
CHEMBL392
 IC50 4.28 4.28 53100.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 293.2 - Chlorocebus sabaeus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 4 IC50 = 40.0 nM 7.4 Displacement of tetra-acetylated histone H4 peptide from recombinant human N-ter... 31789032
Bromodomain-containing protein 4 IC50 = 43.8 nM 7.36 Inhibition of BRD4 bromodomain 2 (unknown origin) incubated for 30 mins by ELISA 31257080
Bromodomain-containing protein 4 IC50 = 67.0 nM 7.17 Inhibition of human BRD4 bromo domain 2 28765013
Bromodomain-containing protein 4 IC50 = 100.0 nM 7.0 Inhibition of biotinylated H4 K5,8,12,16Ac peptide binding to GST-tagged BRD4 br... 30926312
Bromodomain-containing protein 4 Kd = 130.0 nM 6.89 Inhibition of human 6x-His-tagged BRD4 bromodomain 2 expressed in Escherichia co... 30253095
Bromodomain-containing protein 4 IC50 = 132.0 nM 6.88 Binding affinity human BRD4 BD2 incubated for 1 hr by TR-FRET assay 34982556
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to human BRD4 BD2 by isothermal calorimetry analysis 32324999
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to BRD4 BD2 (unknown origin) 33460833
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to BRD4 BD2 (unknown origin) by ITC analysis 38295759
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to human BRD4 BD2 assessed as dissociation constant by isotherm... 38295759
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to BRD4 BD2 (unknown origin) by isothermal titration calorimetr... 34731760
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to human BRD4 BD2 assessed as dissociation constant by ITC anal... 35544982
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to N-terminal His-tagged BRD4 BD2 (unknown origin) by isotherma... 32691591
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Binding affinity to recombinant BRD4 BD2 (unknown origin) incubated for 1 hr by ... 32255647
Bromodomain-containing protein 4 Kd = 135.0 nM 6.87 Inhibition of recombinant human His6-tagged BRD4 bromodomain 2 expressed in Esch... 28195723
Bromodomain-containing protein 4 Ki = 135.0 nM 6.87 Inhibition of his6-tagged BRD4 BD2 (unknown origin) (1 to 477 residues) assessed... 37478496
Bromodomain-containing protein 4 IC50 = 135.0 nM 6.87 Inhibition of BRD4 BD2 (unknown origin) after 1 hr by TR-FRET assay 29649741
Bromodomain-containing protein 4 IC50 = 135.0 nM 6.87 Plate-Based Time-Resolved Fluorescence Energy Transfer (TR-FRET) Assays: Determi... -
Bromodomain-containing protein 4 Kd = 140.0 nM 6.85 Binding affinity to human BRD4 bromodomain 2 expressed in Escherichia coli BL21 ... 26367539
Bromodomain-containing protein 4 Kd = 140.0 nM 6.85 Binding affinity to BRD4 bromodomain 2 (unknown origin) by isothermal titration ... 26572217

Literature References

PubMed DOI Target Context # Activities
23644195 10.1016/j.ejmech.2013.03.062 ADMET 64
23644195 10.1016/j.ejmech.2013.03.062 Liver microsomes 7
29649741 10.1016/j.ejmech.2018.04.006 Bromodomain-containing protein 4 6
32255647 10.1021/acs.jmedchem.0c00035 Bromodomain-containing protein 4 6
26367539 10.1021/acs.jmedchem.5b01135 Bromodomain-containing protein 2 5
30926312 10.1016/j.bmc.2019.03.037 Bromodomain-containing protein 4 5
30253095 10.1021/acs.jmedchem.8b01248 Bromodomain-containing protein 4 5
29649741 10.1016/j.ejmech.2018.04.006 Mus musculus 5
33691794 10.1186/s13148-021-01037-1 A549 4
38295759 10.1021/acs.jmedchem.3c01837 Bromodomain-containing protein 4 4
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
26367539 10.1021/acs.jmedchem.5b01135 Bromodomain-containing protein 4 4
29172540 10.1021/acs.jmedchem.7b00275 MCF7 3
29172540 10.1021/acs.jmedchem.7b00275 MDA-MB-231 3
30926312 10.1016/j.bmc.2019.03.037 Unchecked 3
32153186 10.1021/acs.jmedchem.9b02178 HCT-116 3
27266999 10.1016/j.ejmech.2016.05.057 NON-PROTEIN TARGET 3
28765013 10.1016/j.bmcl.2017.07.054 Bromodomain-containing protein 4 3
31789032 10.1021/acs.jmedchem.9b01010 Bromodomain-containing protein 4 3
32353859 10.1038/s41586-020-2286-9 SARS-CoV-2 3

Data from ChEMBL 36 via Core Engine