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Compound Detail

CHEMBL111589

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COc1cc2c(cc1/C(C)=C\C=C\C(C)=C\C(=O)O)C(C)(C)CCC2(C)C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL111589
Phase Preclinical
Structure Type MOL
InChI Key UPVFFMLTSPBEBW-TWHHPHDDSA-N
6
Targets
12
Activities
2
Assay Types
0
PK Parameters
6
Publications
0
Known Names

Molecular Properties

368.5
MW (Da)
6.03
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.51
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H32O3
MW 368.52
Aromatic Rings 1
Heavy Atoms 27
NP-Likeness 1.23

Activity Summary

EC50 6 meas. best 8.3
Ki 6 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor RXR-beta
CHEMBL1870
 Ki 8.7 8.7 2.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
 Ki 8.7 8.7 2.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
 Ki 8.4 8.4 4.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
 EC50 8.3 8.3 5.0 1
Retinoic acid receptor RXR-beta
CHEMBL1870
 EC50 8.1 8.1 8.0 1
Retinoic acid receptor beta
CHEMBL2008
 EC50 8.1 8.1 8.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
 EC50 8.05 8.05 9.0 1
Retinoic acid receptor gamma
CHEMBL2003
 EC50 7.77 7.77 17.0 1
Retinoic acid receptor alpha
CHEMBL2055
 EC50 7.4 7.4 40.0 1
Retinoic acid receptor alpha
CHEMBL2055
 Ki 6.51 6.51 306.0 1
Retinoic acid receptor beta
CHEMBL2008
 Ki 6.4 6.4 400.0 1
Retinoic acid receptor gamma
CHEMBL2003
 Ki 6.36 6.36 437.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor RXR-alpha Ki = 2.0 nM 8.7 Inhibition of [3H]targretin binding to Retinoid X receptor RXR alpha 8765503
Retinoic acid receptor RXR-beta Ki = 2.0 nM 8.7 Inhibition of [3H]-Targretin binding to Retinoid X receptor RXR beta 8765503
Retinoic acid receptor RXR-gamma Ki = 4.0 nM 8.4 Inhibition of [3H]targretin binding to Retinoid X receptor RXR gamma 8765503
Retinoic acid receptor RXR-alpha EC50 = 5.0 nM 8.3 Transcriptional ativation of Retinoid X receptor RXR alpha 8765503
Retinoic acid receptor RXR-beta EC50 = 8.0 nM 8.1 Transcriptional activation of Retinoid X receptor RXR beta 8765503
Retinoic acid receptor beta EC50 = 8.0 nM 8.1 Transcriptional activation of Retinoic acid receptor RAR beta 8765503
Retinoic acid receptor RXR-gamma EC50 = 9.0 nM 8.05 Transcriptional activation of Retinoid X receptor RXR gamma 8765503
Retinoic acid receptor gamma EC50 = 17.0 nM 7.77 Transcriptional activation of Retinoic acid receptor RAR gamma 8765503
Retinoic acid receptor alpha EC50 = 40.0 nM 7.4 Transcriptional activation of Retinoic acid receptor RAR alpha 8765503
Retinoic acid receptor alpha Ki = 306.0 nM 6.51 Inhibition of [3H]ATRA binding to Retinoic acid receptor RAR alpha 8765503
Retinoic acid receptor beta Ki = 400.0 nM 6.4 Inhibition of [3H]ATRA binding to Retinoic acid receptor RAR beta 8765503
Retinoic acid receptor gamma Ki = 437.0 nM 6.36 Inhibition of [3H]ATRA binding to Retinoic acid receptor RAR gamma 8765503

Literature References

PubMed DOI Target Context # Activities
8765503 10.1021/jm960311d Retinoic acid receptor RXR-alpha 2
8765503 10.1021/jm960311d Retinoic acid receptor RXR-beta 2
8765503 10.1021/jm960311d Retinoic acid receptor RXR-gamma 2
8765503 10.1021/jm960311d Retinoic acid receptor alpha 2
8765503 10.1021/jm960311d Retinoic acid receptor beta 2
8765503 10.1021/jm960311d Retinoic acid receptor gamma 2

Data from ChEMBL 36 via Core Engine