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Compound Detail

CHEMBL442016

ADAROTENE
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O=C(O)/C=C/c1ccc(-c2ccc(O)c(C34CC5CC(CC(C5)C3)C4)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL442016
Name ADAROTENE
Phase Preclinical
Structure Type MOL
InChI Key QAWBIEIZDDIEMW-FPYGCLRLSA-N
19
Targets
27
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

374.5
MW (Da)
5.62
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.68
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H26O3
MW 374.48
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.45

Activity Summary

IC50 24 meas. best 7.09
EC50 3 meas. best 7.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NB-4
CHEMBL614188
 IC50 7.09 7.09 82.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.0 6.6 100.0 3
A2780
CHEMBL614004
 IC50 7.0 7.0 100.0 1
DU-145
CHEMBL613508
 IC50 7.0 7.0 100.0 1
ADMET
CHEMBL612558
 IC50 7.0 7.0 100.0 1
Unchecked
CHEMBL612545
 EC50 7.0 6.85 100.0 2
LNCaP
CHEMBL612518
 IC50 6.92 6.92 120.0 1
A-431
CHEMBL614069
 IC50 6.92 6.76 120.0 2
LoVo
CHEMBL614721
 IC50 6.82 6.82 150.0 1
GBM
CHEMBL614570
 IC50 6.75 6.75 180.0 1
NCI-H460
CHEMBL396
 IC50 6.72 6.71 190.0 2
Retinoic acid receptor beta
CHEMBL2008
 EC50 6.7 6.7 200.0 1
PC-3
CHEMBL390
 IC50 6.68 6.68 210.0 1
IGROV-1
CHEMBL613984
 IC50 6.64 6.64 230.0 3
Me665/2/21
CHEMBL614339
 IC50 6.6 6.6 250.0 1
SAOS-2
CHEMBL614894
 IC50 6.6 6.6 250.0 1
U2OS
CHEMBL615023
 IC50 6.58 6.58 260.0 1
HCT-116
CHEMBL394
 IC50 6.5 6.5 320.0 1
Pup--protein ligase
CHEMBL5169231
 IC50 4.75 4.75 17900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NB-4 IC50 = 82.0 nM 7.09 Concentration of compound required for inhibition of (NB4) human promyelocytic l... 16033272
NB-4 IC50 = 82.0 nM 7.09 Antiproliferative activity against human NB4 cells after 72 hrs 17512204
Unchecked EC50 = 100.0 nM 7.0 Effective concentration against retinoic acid receptor gamma in COS-7 cells co-e... 16033272
A2780 IC50 = 100.0 nM 7.0 Antiproliferative effect of compound on A2780/DX cell line 12620066
DU-145 IC50 = 100.0 nM 7.0 Antiproliferative effect of compound on DU145 cell line expressing mutant p53 12620066
NON-PROTEIN TARGET IC50 = 100.0 nM 7.0 Antiproliferative activity against HMVE cells 17489579
ADMET IC50 = 100.0 nM 7.0 Growth inhibition of HMVE cells after 72 hrs by alamar blue method 18759424
LNCaP IC50 = 120.0 nM 6.92 Antiproliferative effect of compound on LNcaP cell line expressing wild-type p53 12620066
A-431 IC50 = 120.0 nM 6.92 Antiproliferative activity against human A431 cells incubated for 24 hrs drug ex... 22365912
LoVo IC50 = 150.0 nM 6.82 Antiproliferative effect of compound on LoVo cell line expressing wild-type p53 12620066
GBM IC50 = 180.0 nM 6.75 Antiproliferative effect of compound on GBM cell line expressing mutant p53 12620066
NCI-H460 IC50 = 190.0 nM 6.72 Antiproliferative effect of compound on H460 cell line expressing wild-type p53 12620066
Unchecked EC50 = 200.0 nM 6.7 Effective concentration against retinoic acid receptor alpha in COS-7 cells co-e... 16033272
NCI-H460 IC50 = 200.0 nM 6.7 Antiproliferative activity against human NCI-H460 cells incubated for 24 hrs dru... 22365912
Retinoic acid receptor beta EC50 = 200.0 nM 6.7 Effective concentration against retinoic acid receptor beta in COS-7 cells co-ex... 16033272
PC-3 IC50 = 210.0 nM 6.68 Antiproliferative effect of compound on PC3 cell line 12620066
IGROV-1 IC50 = 230.0 nM 6.64 Antiproliferative effect of compound on IGROV-1 cell line expressing wild-type p... 12620066
IGROV-1 IC50 = 230.0 nM 6.64 Concentration of compound required for inhibition of (IGROV-1) human ovarian car... 16033272
IGROV-1 IC50 = 230.0 nM 6.64 Antiproliferative activity against human IGROV1 cells after 72 hrs 17512204
A-431 IC50 = 250.0 nM 6.6 Antiproliferative effect of compound on A431 cell line expressing mutant p53 12620066

Literature References

PubMed DOI Target Context # Activities
35926511 10.1021/acs.jmedchem.2c00289 Pup--protein ligase 9
22365912 10.1016/j.bmc.2012.01.042 Mus musculus 5
22365912 10.1016/j.bmc.2012.01.042 No relevant target 5
17512204 10.1016/j.bmc.2007.04.057 IGROV-1 4
22136251 10.1021/jm2011436 MDA-MB-231 4
12620066 10.1021/jm025593y IGROV-1 4
12620066 10.1021/jm025593y DU-145 4
16033272 10.1021/jm049440h Unchecked 3
22365912 10.1016/j.bmc.2012.01.042 NCI-H460 3
18759424 10.1021/jm800456k MDA-MB-231 2
18759424 10.1021/jm800456k ADMET 2
15214780 10.1021/jm030524k NCI-H460 2
22136251 10.1021/jm2011436 Unchecked 2
21548569 10.1021/jm200051z Retinoic acid receptor gamma 2
21548569 10.1021/jm200051z Unchecked 2
18759424 10.1021/jm800456k Unchecked 2
21548569 10.1021/jm200051z Retinoic acid receptor beta 2
15214780 10.1021/jm030524k MDA-MB-231 2
16033272 10.1021/jm049440h IGROV-1 2
15214780 10.1021/jm030524k HL-60 2

Data from ChEMBL 36 via Core Engine