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Compound Detail

CHEMBL275311

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C/C(=C\c1ccc(C(=O)O)cc1)c1ccc2c(c1)C(C)(C)CCC2(C)C

Basic Information

ChEMBL ID CHEMBL275311
Phase Preclinical
Structure Type MOL
InChI Key FOIVPCKZDPCJJY-JQIJEIRASA-N
11
Targets
45
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

348.5
MW (Da)
6.29
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.66
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C24H28O2
MW 348.49
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.37

Activity Summary

EC50 24 meas. best 9.74
IC50 11 meas. best 10.22
Ki 6 meas. best 9.3
Kd 4 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mus musculus
CHEMBL375
IC50 10.22 10.22 0.1 2
Retinoic acid receptor alpha
CHEMBL2055
EC50 9.74 7.8013 0.2 8
Retinoic acid receptor beta
CHEMBL2008
Ki 9.3 8.9667 0.5 3
Retinoic acid receptor gamma
CHEMBL2003
EC50 8.7 8.5114 2.0 7
Retinoic acid receptor beta
CHEMBL2008
EC50 8.52 8.4257 3.0 7
Retinoic acid receptor gamma
CHEMBL2003
Ki 8.3 8.3 5.0 1
Retinoic acid receptor beta
CHEMBL2008
IC50 8.3 8.3 5.0 1
Retinoic acid receptor beta
CHEMBL2008
Kd 8.3 8.3 5.0 1
Retinoic acid receptor alpha
CHEMBL2055
Ki 7.68 7.68 21.0 1
Retinoic acid receptor gamma
CHEMBL2003
IC50 7.58 7.58 26.0 1
Retinoic acid receptor gamma
CHEMBL2003
Kd 7.58 7.58 26.0 2
Retinoic acid receptor alpha
CHEMBL2055
IC50 7.44 7.44 36.0 1
Retinoic acid receptor alpha
CHEMBL2055
Kd 7.44 7.44 36.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.43 5.43 3700.0 1
Unchecked
CHEMBL612545
IC50 5.36 4.905 4400.0 2
Cytochrome P450 26A1
CHEMBL5141
IC50 5.25 5.25 5600.0 1
Nuclear receptor ROR-gamma
CHEMBL1741186
EC50 5.05 5.05 9000.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
EC50 5.0 5.0 10000.0 1
Plasmodium falciparum
CHEMBL364
IC50 4.8 4.8 15848.9 1
Unchecked
CHEMBL612545
Ki 4.35 4.35 45000.0 1
HL-60
CHEMBL383
IC50 4.34 4.34 46000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mus musculus IC50 = 0.06 nM 10.22 Inhibition of Chondrogenesis in day 11 embryonic limb bud cells 8784454
Mus musculus IC50 = 0.06 nM 10.22 In vitro inhibition of chondrogenesis in mouse embryo limb bud cells 7636843
Retinoic acid receptor alpha EC50 = 0.18 nM 9.74 Agonist activity at human RARalpha expressed in HEK293 cells by luciferase repor... 25305688
Retinoic acid receptor beta Ki = 0.5 nM 9.3 Binding affinity towards cRAR-beta-2 receptor by displacing 0.82 nM 3[H]all-tran... -
Retinoic acid receptor beta Ki = 0.5 nM 9.3 Binding affinity towards cRAR-beta-2 receptor by displacing 1.1 nM 3[H]-9-cis-RA -
Retinoic acid receptor gamma EC50 = 2.0 nM 8.7 Agonist activity for retinoic acid receptor RAR gamma in transcriptional activat... -
Retinoic acid receptor gamma EC50 = 2.0 nM 8.7 Binding affinity against retinoic Acid gamma receptors co-transfected into CV-1 ... 8308867
Retinoic acid receptor gamma EC50 = 2.0 nM 8.7 Transactivation potency for Retinoic acid receptor gamma -
Retinoic acid receptor gamma EC50 = 2.4 nM 8.62 Transcriptional activation for RAR gamma receptor -
Retinoic acid receptor gamma EC50 = 2.4 nM 8.62 Transcriptional activation of retinoic acid receptor RAR gamma -
Retinoic acid receptor gamma EC50 = 2.4 nM 8.62 Transcriptional activation of Retinoic acid receptor RAR gamma 7636843
Retinoic acid receptor beta EC50 = 3.0 nM 8.52 Transactivation potency for Retinoic acid receptor beta -
Retinoic acid receptor beta EC50 = 3.0 nM 8.52 Binding affinity against retinoic Acid beta receptors co-transfected into CV-1 c... 8308867
Retinoic acid receptor beta EC50 = 3.0 nM 8.52 Agonist activity for retinoic acid receptor RAR beta in transcriptional activati... -
Retinoic acid receptor beta EC50 = 4.0 nM 8.4 Transcriptional activation for RAR beta receptor -
Retinoic acid receptor beta EC50 = 4.0 nM 8.4 Transcriptional activation of retinoic acid receptor RAR beta -
Retinoic acid receptor beta EC50 = 4.0 nM 8.4 Transcriptional activation of Retinoic acid receptor RAR beta 7636843
Retinoic acid receptor gamma Ki = 5.0 nM 8.3 Binding affinity to retinoic acid receptor (RAR) gamma using [3H]CD 367 as radio... 8544175
Retinoic acid receptor beta Kd = 5.0 nM 8.3 Binding affinity for Retinoic acid receptor beta -
Retinoic acid receptor beta IC50 = 5.0 nM 8.3 Binding affinity against retinoic Acid beta receptor using [3H]- -9-cis-Retinoic... 8308867

Literature References

PubMed DOI Target Context # Activities
9357524 10.1021/jm970196m Mus musculus 60
8230100 10.1021/jm00073a013 C3H 10T1/2 20
9357524 10.1021/jm970196m Rattus norvegicus 12
6208361 10.1021/jm00377a022 Unchecked 12
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
9357524 10.1021/jm970196m ADMET 6
6208361 10.1021/jm00377a022 Mus musculus 6
34812616 10.1021/acs.jmedchem.1c01547 Unchecked 5
6208361 10.1021/jm00377a022 Cricetinae gen. sp. 4
15261282 10.1016/j.bmcl.2004.06.002 NB-4 4
10201840 10.1016/s0960-894x(99)00077-3 Mus musculus 4
24900875 10.1021/ml400521f Retinoic acid receptor RXR-beta 4
19938842 10.1021/jm901309r No relevant target 3
19938842 10.1021/jm901309r Beta-lactoglobulin 3
2738885 10.1021/jm00127a018 Oryctolagus cuniculus 3
- 10.1016/S0960-894X(97)00420-4 Retinoic acid receptor beta 2
10890153 10.1016/s0960-894x(00)00244-4 Retinoic acid receptor alpha 2
10890153 10.1016/s0960-894x(00)00244-4 Retinoic acid receptor gamma 2
10890153 10.1016/s0960-894x(00)00244-4 Retinoic acid receptor RXR-alpha 2
8410972 10.1021/jm00070a003 Retinoic acid receptor beta 2

Data from ChEMBL 36 via Core Engine