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Compound Detail

CHEMBL235191

TACEDINALINE
🧪 Phase III
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🧪 Phase III
CC(=O)Nc1ccc(C(=O)Nc2ccccc2N)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL235191
Name TACEDINALINE
Phase Phase III
Structure Type MOL
InChI Key VAZAPHZUAVEOMC-UHFFFAOYSA-N

Known Names

Acetyldinaline CI-994 GOE 5549 GOE-5549 PD 123654 PD-123654 Tacedinalina Tacedinaline
26
Targets
96
Activities
3
Assay Types
5
PK Parameters
20
Publications
8
Known Names
3
Indications
1
Mechanisms

Molecular Properties

269.3
MW (Da)
2.48
ALogP
3
HBA
3
HBD
84.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Year 2002

Extended Properties

Molecular Formula C15H15N3O2
MW 269.30
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -1.29

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histone deacetylase inhibitor INHIBITOR Histone deacetylase ✓ ✓

Indications

Lung Neoplasms Multiple Myeloma Pancreatic Neoplasms

Activity Summary

IC50 87 meas. best 7.41
Ki 7 meas. best 7.3
EC50 2 meas. best 5.42

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 1
CHEMBL325
 IC50 7.41 6.3444 39.0 18
Histone deacetylase 3
CHEMBL1829
 IC50 7.34 6.8925 46.0 4
Histone deacetylase 1
CHEMBL325
 Ki 7.3 6.57 50.0 2
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.13 6.635 74.0 2
Histone deacetylase 3
CHEMBL1829
 Ki 6.98 6.23 105.0 3
Unchecked
CHEMBL612545
 IC50 6.89 5.7833 130.0 6
Histone deacetylase 2
CHEMBL1937
 IC50 6.83 6.093 147.0 10
Histone deacetylase 2
CHEMBL1937
 Ki 6.72 6.19 190.0 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 6.72 6.72 190.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 5.84 5.84 1440.0 1
Histone deacetylase
CHEMBL2093865
 IC50 5.74 5.5725 1810.0 4
JeKo-1
CHEMBL4296445
 IC50 5.72 5.72 1900.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.55 5.55 2830.0 1
HL-60
CHEMBL383
 IC50 5.55 5.55 2800.0 1
Histone deacetylase
CHEMBL2093865
 EC50 5.42 5.42 3810.0 1
HCT-116
CHEMBL394
 IC50 5.4 5.1329 4000.0 7
MM1.S
CHEMBL4296471
 IC50 5.33 5.33 4700.0 1
NCI-H1299
CHEMBL612255
 IC50 5.17 4.7033 6790.0 3
LNCaP
CHEMBL612518
 IC50 5.13 5.13 7400.0 1
HCT-116
CHEMBL394
 EC50 5.08 5.08 8400.0 1
NIH3T3
CHEMBL614822
 IC50 5.04 5.04 9050.0 2
A-375
CHEMBL613859
 IC50 5.02 4.9675 9640.0 4
NCI-H460
CHEMBL396
 IC50 5.01 5.01 9700.0 1
HepG2
CHEMBL395
 IC50 5.0 4.82 10000.0 3
A549
CHEMBL392
 IC50 4.99 4.7783 10170.0 6
MDA-MB-231
CHEMBL400
 IC50 4.96 4.96 10900.0 1
MGC-803
CHEMBL3706566
 IC50 4.94 4.94 11600.0 2
MCF7
CHEMBL387
 IC50 4.88 4.88 13160.0 1
HeLa
CHEMBL399
 IC50 4.87 4.78 13430.0 3
SMMC-7721
CHEMBL613831
 IC50 4.85 4.81 14060.0 2
NCI-H661
CHEMBL1075544
 IC50 4.7 4.7 20000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.26 uL/min Homo sapiens
T1/2 23.1 hr Homo sapiens
T1/2 2.317 hr Homo sapiens
T1/2 0.8333 hr Homo sapiens
T1/2 3.333 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 1 IC50 = 39.0 nM 7.41 Inhibition of Histone Deacetylase Enzymatic Activity: The following non-trypsin ... -
Histone deacetylase 1 IC50 = 39.0 nM 7.41 Inhibition of Histone Deacetylase Enzymatic Activity: The following non-trypsin ... -
Histone deacetylase 1 IC50 = 41.0 nM 7.39 Inhibition of recombinant human full length C-terminal His/FALG-tagged HDAC1 exp... 30735902
Histone deacetylase 1 IC50 = 41.0 nM 7.39 IC50 Assay: IC50 measurements were conducted by BPS Biosciences (Table 1) or by ... -
Histone deacetylase 3 IC50 = 46.0 nM 7.34 Inhibition of recombinant human full length HDAC3 using FAM-labeled acetylated p... 30735902
Histone deacetylase 3 IC50 = 46.0 nM 7.34 IC50 Assay: IC50 measurements were conducted by BPS Biosciences (Table 1) or by ... -
Histone deacetylase 1 Ki = 50.0 nM 7.3 Inhibition of human HDAC1 20139990
Histone deacetylase 1 IC50 = 60.0 nM 7.22 Inhibition of human recombinant HDAC1 (1 to 482 residues) expressed in Baculovir... 28885834
Bromodomain-containing protein 4 IC50 = 74.0 nM 7.13 Inhibition of BRD4 BD2 (unknown origin) 34107385
Histone deacetylase 3 Ki = 105.0 nM 6.98 Binding affinity to HDAC3 (unknown origin) using Ac-LGKac-AMC as substrate asses... 37651268
Histone deacetylase 3 IC50 = 106.2 nM 6.97 Inhibition of HDAC3 (unknown origin) using Boc-Lys(acetyl)-AMC as substrate prei... 37948955
Histone deacetylase 1 IC50 = 130.0 nM 6.89 Inhibition of recombinant human C-terminal His/FLAG-tagged HDAC1 (1 to 482 resid... 32971411
Unchecked IC50 = 130.0 nM 6.89 Inhibition of HDAC3-SMRT (unknown origin) using Boc- (Ac)Lys-AMC as substrate pr... 35293758
Histone deacetylase 2 IC50 = 147.0 nM 6.83 Inhibition of recombinant human full length C-terminal FLAG-tagged HDAC2 express... 30735902
Histone deacetylase 2 IC50 = 147.0 nM 6.83 IC50 Assay: IC50 measurements were conducted by BPS Biosciences (Table 1) or by ... -
Histone deacetylase 2 Ki = 190.0 nM 6.72 Inhibition of human HDAC2 20139990
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) IC50 = 190.0 nM 6.72 Inhibition of human recombinant C-terminal His-tagged HDAC3 (1 to 428 residues)/... 32971411
Histone deacetylase 2 IC50 = 363.9 nM 6.44 Inhibition of HDAC2 (unknown origin) using Boc-Lys(acetyl)-AMC as substrate prei... 37948955
Histone deacetylase 1 IC50 = 394.2 nM 6.4 Inhibition of HDAC1 (unknown origin) using Boc-Lys(acetyl)-AMC as substrate prei... 37948955
Unchecked IC50 = 530.0 nM 6.28 Inhibition of HDAC1-CoREST-LSD1 (unknown origin) using Boc- (Ac)Lys-AMC as subst... 35293758

Literature References

PubMed DOI Target Context # Activities
31103900 10.1016/j.ejmech.2019.05.007 A549 29
37948955 10.1016/j.ejmech.2023.115915 JeKo-1 29
31003060 10.1016/j.ejmech.2019.04.017 SMMC-7721 26
28391133 10.1016/j.ejmech.2017.03.038 A549 17
30108928 10.1039/C7MD00476A A-375 15
32940035 10.1021/acs.jmedchem.0c01541 No relevant target 15
30258535 10.1021/acsmedchemlett.8b00099 Unchecked 13
31223439 10.1021/acsmedchemlett.8b00440 Histone deacetylase 6 10
35293758 10.1021/acs.jmedchem.1c02179 HCT-116 9
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 1 6
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 2 6
37651268 10.1021/acs.jmedchem.3c01160 Histone deacetylase 3 6
31223439 10.1021/acsmedchemlett.8b00440 Unchecked 6
28885834 10.1021/acs.jmedchem.7b00467 HCT-116 4
33691794 10.1186/s13148-021-01037-1 A549 4
32971411 10.1016/j.ejmech.2020.112800 Unchecked 4
31003060 10.1016/j.ejmech.2019.04.017 A549 4
31003060 10.1016/j.ejmech.2019.04.017 A-375 3
31103900 10.1016/j.ejmech.2019.05.007 HeLa 3
29202397 10.1016/j.ejmech.2017.08.041 HeLa 3

Data from ChEMBL 36 via Core Engine