Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL2170177

Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
COc1ccc(Cn2ccc3ccc(C(=O)NO)cc32)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2170177
Phase Preclinical
Structure Type MOL
InChI Key AJRGHIGYPXNABY-UHFFFAOYSA-N
25
Targets
100
Activities
4
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

296.3
MW (Da)
2.82
ALogP
4
HBA
2
HBD
63.5
PSA (Ų)
0.57
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H16N2O3
MW 296.33
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -1.12

Activity Summary

IC50 93 meas. best 8.39
Kd 4 meas. best 8.51
EC50 2 meas. best 5.75
Ki 1 meas. best 5.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histone deacetylase 8
CHEMBL3192
 Kd 8.51 6.89 3.1 3
Histone deacetylase 8
CHEMBL3192
 IC50 8.39 7.5129 4.0 31
Histone deacetylase 7
CHEMBL2716
 IC50 8.0 8.0 10.0 1
Histone deacetylase 8
CHEMBL3797017
 Kd 6.43 6.43 367.0 1
Histone deacetylase 8
CHEMBL3797017
 IC50 6.36 6.36 435.6 3
Histone deacetylase 11
CHEMBL3310
 IC50 6.32 6.32 482.0 1
NCI-N87
CHEMBL614197
 IC50 5.82 5.82 1500.0 1
Unchecked
CHEMBL612545
 IC50 5.79 5.4175 1630.0 4
Histone deacetylase 2
CHEMBL1937
 IC50 5.76 5.135 1740.0 2
Hepatitis C virus
CHEMBL379
 EC50 5.75 5.75 1800.0 1
K562
CHEMBL385
 IC50 5.7 5.68 2010.0 2
A549
CHEMBL392
 IC50 5.7 5.1267 2000.0 3
Histone deacetylase 8
CHEMBL3192
 Ki 5.7 5.7 2000.0 1
SH-SY5Y
CHEMBL614910
 IC50 5.62 5.62 2380.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 5.54 5.1969 2900.0 13
MCF7
CHEMBL387
 IC50 5.53 5.53 2980.0 1
BE(2)-C
CHEMBL4483229
 IC50 5.51 5.105 3100.0 2
DOHH-2
CHEMBL2366181
 IC50 5.5 5.5 3140.0 1
Histone deacetylase 1
CHEMBL325
 IC50 5.42 5.0691 3800.0 11
Jurkat
CHEMBL397
 IC50 5.35 5.35 4500.0 2
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2)
CHEMBL2111363
 IC50 5.15 4.675 7100.0 2
MOLT-4
CHEMBL614177
 IC50 5.03 5.03 9400.0 1
Histone deacetylase 4
CHEMBL3524
 IC50 5.0 5.0 10000.0 1
HEL
CHEMBL613888
 IC50 4.97 4.97 10800.0 1
Polyamine deacetylase HDAC10
CHEMBL5103
 IC50 4.89 4.792 13000.0 5
MDA-MB-231
CHEMBL400
 IC50 4.79 4.79 16080.0 1
PC-3
CHEMBL390
 IC50 4.72 4.72 19200.0 1
HCT-116
CHEMBL394
 IC50 4.66 4.66 21900.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6946.0 ng.hr.mL-1 Mus musculus
Cmax 57600.0 nM Mus musculus
MRT 0.45 hr Mus musculus
T1/2 3.3 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histone deacetylase 8 Kd = 3.1 nM 8.51 Binding affinity to His-tagged recombinant human HDAC8 by SPR assay 32672458
Histone deacetylase 8 IC50 = 4.03 nM 8.39 Inhibition of N-terminal His-tagged full length human HDAC8 expressed in baculov... 32672458
Histone deacetylase 8 IC50 = 6.6 nM 8.18 Inhibition of recombinant HDAC8 (unknown origin) expressed in Escherichia coli u... 28835796
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of human recombinant HDAC8 using fluor de Lys as substrate preincubat... 23010266
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of recombinant HDAC8 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-... 26937828
Histone deacetylase 7 IC50 = 10.0 nM 8.0 Inhibition of HDAC7 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-4... 28453994
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) preincubated for 15 mins followed by acetyl... 29505935
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) after 15 mins by fluorescence assay 25240614
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC-8 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-... -
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-4... 28771357
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-4... 27774131
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-4... 30594678
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of HDAC8 (unknown origin) assessed as release of fluorogenic AMC pre-... 37429084
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of human recombinant HDAC8 37429084
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of human HDAC8 using acetyl-Gly-Ala-(N-acetyl-Lys)-amino-4-methylcoum... 18256683
Histone deacetylase 8 IC50 = 10.0 nM 8.0 Inhibition of human recombinant HDAC8 using H2N-Arg-His-Lys(Ac)-Lys(Ac)-AMC as s... 34392190
Histone deacetylase 8 IC50 = 12.0 nM 7.92 Inhibition of human recombinant HDAC8 after 30 mins using fluorogenic substrate ... 30004697
Histone deacetylase 8 IC50 = 12.0 nM 7.92 Inhibition of HDAC8 (unknown origin) measured by fluorometry assay 35797900
Histone deacetylase 8 IC50 = 18.3 nM 7.74 HDAC Inhibition Assay: All histone deacetylases were purchased from BPS Bioscien... -
Histone deacetylase 8 IC50 = 24.0 nM 7.62 Inhibition of recombinant human HDAC8 using Boc-Lys (trifluoroacetyl)-AMC as sub... 34006099

Literature References

PubMed DOI Target Context # Activities
36516047 10.1021/acs.jmedchem.2c00739 A549 18
18256683 10.1038/leu.2008.9 Jurkat 17
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
28109947 10.1016/j.ejmech.2016.12.032 Unchecked 12
30347148 10.1021/acs.jmedchem.8b01087 Histone deacetylase 8 12
- 10.6019/CHEMBL4689842 U2OS 10
32672458 10.1021/acs.jmedchem.0c01025 Unchecked 10
18256683 10.1038/leu.2008.9 J.gamma1 8
30347148 10.1021/acs.jmedchem.8b01087 Unchecked 8
29150330 10.1016/j.ejmech.2017.10.076 U-937 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
18256683 10.1038/leu.2008.9 Unchecked 6
29505935 10.1016/j.ejmech.2018.02.065 Unchecked 5
36516047 10.1021/acs.jmedchem.2c00739 Histone deacetylase 8 5
28771357 10.1021/acs.jmedchem.7b00115 Unchecked 5
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
29190092 10.1021/acs.jmedchem.7b01447 Histone deacetylase 8 4
32672458 10.1021/acs.jmedchem.0c01025 Histone deacetylase 8 4

Data from ChEMBL 36 via Core Engine