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Compound Detail

CHEMBL1180

O-DEMETHYLATED ADAPALENE
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O=C(O)c1ccc2cc(-c3ccc(O)c(C45CC6CC(CC(C6)C4)C5)c3)ccc2c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1180
Name O-DEMETHYLATED ADAPALENE
Phase Preclinical
Structure Type MOL
InChI Key LDGIHZJOIQSHPB-UHFFFAOYSA-N
24
Targets
33
Activities
3
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

398.5
MW (Da)
6.38
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.54
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H26O3
MW 398.50
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness 0.25

Activity Summary

IC50 25 meas. best 6.89
EC50 5 meas. best 7.31
Ki 3 meas. best 7.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor gamma
CHEMBL2003
 EC50 7.31 7.305 49.0 2
Retinoic acid receptor gamma
CHEMBL2003
 Ki 7.11 7.11 77.0 1
OVCAR-3
CHEMBL614213
 IC50 6.89 6.89 130.0 1
Retinoic acid receptor beta
CHEMBL2008
 EC50 6.65 6.65 226.0 2
DU-145
CHEMBL613508
 IC50 6.55 6.55 280.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.52 6.3133 300.0 3
LNCaP
CHEMBL612518
 IC50 6.5 6.5 320.0 1
ADMET
CHEMBL612558
 IC50 6.48 6.48 330.0 1
IGROV-1
CHEMBL613984
 IC50 6.46 6.46 350.0 3
NB-4
CHEMBL614188
 IC50 6.4 6.4 400.0 2
Me665/2/21
CHEMBL614339
 IC50 6.38 6.38 420.0 1
PC-3
CHEMBL390
 IC50 6.37 6.37 430.0 1
NCI-H460
CHEMBL396
 IC50 6.37 6.37 430.0 1
U2OS
CHEMBL615023
 IC50 6.36 6.36 440.0 1
LoVo
CHEMBL614721
 IC50 6.31 6.31 490.0 1
A-431
CHEMBL614069
 IC50 6.29 6.29 510.0 1
GBM
CHEMBL614570
 IC50 6.26 6.26 550.0 1
HCT-116
CHEMBL394
 IC50 6.17 6.17 680.0 1
SAOS-2
CHEMBL614894
 IC50 6.17 6.17 670.0 1
QGY-7703
CHEMBL4296490
 IC50 5.62 5.62 2380.0 1
Retinoic acid receptor beta
CHEMBL2008
 Ki 5.61 5.61 2480.0 1
HepG2
CHEMBL395
 IC50 5.53 5.53 2930.0 1
SMMC-7721
CHEMBL613831
 IC50 5.28 5.28 5250.0 1
Retinoic acid receptor alpha
CHEMBL2055
 Ki 5.19 5.19 6500.0 1
L02
CHEMBL4296457
 IC50 5.0 5.0 10080.0 1
Unchecked
CHEMBL612545
 EC50 4.92 4.92 11900.0 1

Pharmacokinetic Data

Parameter Value Units Species
Fu 0.0001 - Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor gamma EC50 = 49.0 nM 7.31 Agonist activity at GAL4 DNA-binding domain-tagged RARgamma (unknown origin) lig... 29706423
Retinoic acid receptor gamma EC50 = 50.0 nM 7.3 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
Retinoic acid receptor gamma Ki = 77.0 nM 7.11 Binding affinity to retinoic acid receptor (RAR) gamma using [3H]CD 367 as radio... 8544175
OVCAR-3 IC50 = 130.0 nM 6.89 Antiproliferative activity against human OVCAR3 cell 21548569
Retinoic acid receptor beta EC50 = 226.0 nM 6.65 Agonist activity at GAL4 DNA-binding domain-tagged RARbeta (unknown origin) liga... 29706423
Retinoic acid receptor beta EC50 = 226.0 nM 6.65 Affinity On-target Cellular interaction: (Reporter gene assay (HEK293T cells)) E... -
DU-145 IC50 = 280.0 nM 6.55 Antiproliferative effect of compound on DU145 cell line expressing mutant p53 12620066
NON-PROTEIN TARGET IC50 = 300.0 nM 6.52 Antiproliferative activity against HMVE cells 17489579
LNCaP IC50 = 320.0 nM 6.5 Antiproliferative effect of compound on LNcaP cell line expressing wild-type p53 12620066
ADMET IC50 = 330.0 nM 6.48 Growth inhibition of HMVE cells after 72 hrs by alamar blue method 18759424
IGROV-1 IC50 = 350.0 nM 6.46 Antiproliferative effect of compound on IGROV-1 cell line expressing wild-type p... 12620066
IGROV-1 IC50 = 350.0 nM 6.46 Concentration of compound required for inhibition of (IGROV-1) human ovarian car... 16033272
IGROV-1 IC50 = 350.0 nM 6.46 Concentration of compound required for inhibition of (IGROV-1) human ovarian car... 16033272
NB-4 IC50 = 400.0 nM 6.4 Concentration of compound required for inhibition of (NB4) human promyelocytic l... 16033272
NB-4 IC50 = 400.0 nM 6.4 Concentration of compound required for inhibition of (NB4) human promyelocytic l... 16033272
Me665/2/21 IC50 = 420.0 nM 6.38 Antiproliferative effect of compound on Me665/2/21 cell line expressing mutant p... 12620066
PC-3 IC50 = 430.0 nM 6.37 Antiproliferative effect of compound on PC3 cell line 12620066
NCI-H460 IC50 = 430.0 nM 6.37 Antiproliferative effect of compound on H460 cell line expressing wild-type p53 12620066
U2OS IC50 = 440.0 nM 6.36 Antiproliferative effect of compound on U2OS cell line expressing wild-type p53 12620066
LoVo IC50 = 490.0 nM 6.31 Antiproliferative effect of compound on LoVo cell line expressing wild-type p53 12620066

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 346
- 10.6019/CHEMBL4689842 Fibroblast 345
- 10.6019/CHEMBL4689842 U2OS 344
32184975 10.1021/acsmedchemlett.9b00159 Staphylococcus aureus 7
12620066 10.1021/jm025593y IGROV-1 4
16033272 10.1021/jm049440h IGROV-1 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
32171615 10.1016/j.bmcl.2020.127099 Staphylococcus aureus 4
22136251 10.1021/jm2011436 MDA-MB-231 4
12620066 10.1021/jm025593y DU-145 4
- 10.6019/CHEMBL5724696 TERT-RPE1 4
17489579 10.1021/jm0613323 Unchecked 2
29706423 10.1016/j.bmcl.2018.04.036 Unchecked 2
21548569 10.1021/jm200051z Retinoic acid receptor alpha 2
21548569 10.1021/jm200051z Unchecked 2
15214780 10.1021/jm030524k NCI-H460 2
15214780 10.1021/jm030524k MDA-MB-231 2
15214780 10.1021/jm030524k HL-60 2
21548569 10.1021/jm200051z Retinoic acid receptor gamma 2
18759424 10.1021/jm800456k ADMET 2

Data from ChEMBL 36 via Core Engine