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Compound Detail

CHEMBL42314

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C/C(=C/C=C/C(C)=C/C(=O)O)c1cc(C(C)(C)C)cc(C(C)(C)C)c1OCC(F)F

Basic Information

ChEMBL ID CHEMBL42314
Phase Preclinical
Structure Type MOL
InChI Key BHIBZAZKKARFIM-XRYBSMBUSA-N
13
Targets
24
Activities
3
Assay Types
7
PK Parameters
20
Publications
0
Known Names

Molecular Properties

420.5
MW (Da)
6.92
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.38
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H34F2O3
MW 420.54
Aromatic Rings 1
Heavy Atoms 30
NP-Likeness 0.31

Activity Summary

Ki 17 meas. best 8.82
EC50 4 meas. best 8.52
IC50 3 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor RXR-alpha
CHEMBL2061
Ki 8.82 8.415 1.5 4
RXR alpha/PPAR gamma
CHEMBL2111394
EC50 8.52 8.515 3.0 2
Retinoic acid receptor RXR-alpha
CHEMBL4431
Ki 8.52 8.52 3.0 1
Retinoic acid receptor RXR-beta
CHEMBL1870
Ki 8.4 8.075 4.0 2
Retinoic acid receptor RXR-alpha
CHEMBL2061
IC50 8.1 8.1 8.0 1
Retinoic acid receptor RXR-alpha
CHEMBL4431
IC50 8.1 8.1 8.0 1
Retinoic acid receptor RXR-beta
CHEMBL2805
Ki 8.05 8.05 9.0 1
Retinoic acid receptor RXR-alpha
CHEMBL2061
EC50 7.96 7.96 11.0 1
Retinoic acid receptor RXR-gamma
CHEMBL4277
Ki 7.92 7.92 12.0 1
Retinoic acid receptor RXR-gamma
CHEMBL2004
Ki 7.41 7.245 39.0 2
Retinoic acid receptor alpha
CHEMBL2055
Ki 7.27 7.27 54.0 1
Unchecked
CHEMBL612545
EC50 6.88 6.88 131.5 1
Retinoic acid receptor alpha
CHEMBL2269
Ki 5.56 5.56 2745.0 1
Retinoic acid receptor beta
CHEMBL2008
Ki 5.33 5.175 4687.0 2
Peroxisome proliferator-activated receptor gamma
CHEMBL4797
Ki 5.25 5.25 5590.0 1
Retinoic acid receptor gamma
CHEMBL2003
Ki 5.0 5.0 10000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3800.0 ng.hr.mL-1 Mus musculus
AUC 2090.0 ng.hr.mL-1 Mus musculus
Cmax 1807.2 nM Mus musculus
Cmax 1810.0 nM Mus musculus
Cmax 1.2 ug hr ml-1 Mus musculus
Tmax 1.0 hr Mus musculus
Tmax 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor RXR-alpha Ki = 1.5 nM 8.82 Binding affinity against RXR alpha receptor using [3H]9-cis-RA as radioligand in... 14592510
Retinoic acid receptor RXR-alpha Ki = 2.7 nM 8.57 Inhibition of 3[H]9-cis-retinoic acid binding to Retinoic acid receptor RXR-alph... 12951091
RXR alpha/PPAR gamma EC50 = 3.0 nM 8.52 Transcriptional activity against RXR:PPAR-gamma synergy was determined in vitro 12801232
Retinoic acid receptor RXR-alpha Ki = 3.0 nM 8.52 Binding affinity for Retinoic acid receptor RXR-alpha was determined by competin... 12954061
Retinoic acid receptor RXR-alpha Ki = 3.0 nM 8.52 Binding affinity against Retinoic acid receptor RXR-alpha was determined in vitr... 12801232
RXR alpha/PPAR gamma EC50 = 3.1 nM 8.51 Synergistic activation of BRL-49653 mediated PPAR gamma and retinoid X receptor ... 12951091
Retinoic acid receptor RXR-beta Ki = 4.0 nM 8.4 Displacement of [3H]9-cis-RA from RXR beta receptor in CV-1 cells 14592510
Retinoic acid receptor RXR-alpha IC50 = 8.0 nM 8.1 In vitro transcriptional activation in CV-1 cells expressing RXR-alpha 12954061
Retinoic acid receptor RXR-alpha IC50 = 8.0 nM 8.1 Inhibitory activity against Retinoic acid receptor RXR-alpha antagonist was dete... 12801232
Retinoic acid receptor RXR-beta Ki = 9.0 nM 8.05 Binding affinity for Retinoic acid receptor RXR-beta was determined by competing... 12954061
Retinoic acid receptor RXR-alpha EC50 = 11.0 nM 7.96 Transcriptional activation in CV-1 cells expressing Retinoic X receptor alpha 15006411
Retinoic acid receptor RXR-gamma Ki = 12.0 nM 7.92 Binding affinity for Retinoic acid receptor RXR-gamma was determined by competin... 12954061
Retinoic acid receptor RXR-alpha Ki = 18.0 nM 7.75 Binding affinity against Retinoic acid receptor RXR-alpha by [3H]9-cis-RA displa... 15006411
Retinoic acid receptor RXR-beta Ki = 18.0 nM 7.75 Displacement of [3H]9-cis-RA from Retinoic X receptor beta 15006411
Retinoic acid receptor RXR-gamma Ki = 39.0 nM 7.41 Displacement of [3H]9-cis-RA from retinoic X receptor gamma 15006411
Retinoic acid receptor alpha Ki = 54.0 nM 7.27 Binding affinity against RAR alpha receptor using [3H]ATRA as radioligand in CV-... 14592510
Retinoic acid receptor RXR-gamma Ki = 84.0 nM 7.08 Binding affinity against RXR gamma receptor using [3H]9-cis-RA as radioligand in... 14592510
Unchecked EC50 = 131.5 nM 6.88 In vitro evaluation against RXR-alpha/PPAR-gamma in CV-1 cells by cotransfection... 12954061
Retinoic acid receptor alpha Ki = 2745.0 nM 5.56 Binding affinity for Retinoic acid receptor alpha was determined by competing wi... 12954061
Retinoic acid receptor beta Ki = 4687.0 nM 5.33 Binding affinity for Retinoic acid receptor beta was determined by competing wit... 12954061

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL4689842 Fibroblast 7
15006411 10.1016/j.bmcl.2003.12.089 Retinoic acid receptor RXR-alpha 5
12801232 10.1021/jm020340q Retinoic acid receptor RXR-alpha 5
12954061 10.1021/jm020401k Retinoic acid receptor RXR-alpha 5
12954061 10.1021/jm020401k Unchecked 4
14592510 10.1016/j.bmcl.2003.08.048 Mus musculus 4
12951091 10.1016/s0960-894x(03)00703-0 Retinoic acid receptor RXR-alpha 3
12951091 10.1016/s0960-894x(03)00703-0 Mus musculus 3
12801232 10.1021/jm020340q Unchecked 2
12801232 10.1021/jm020340q Mus musculus 2
12801232 10.1021/jm020340q RXR alpha/PPAR gamma 2
15006411 10.1016/j.bmcl.2003.12.089 Retinoic acid receptor RXR-gamma 2
15006411 10.1016/j.bmcl.2003.12.089 Retinoic acid receptor RXR-beta 2
12951091 10.1016/s0960-894x(03)00703-0 RXR alpha/PPAR gamma 2
12954061 10.1021/jm020401k Rattus norvegicus 2
12801232 10.1021/jm020340q Rattus norvegicus 2
12951091 10.1016/s0960-894x(03)00703-0 Unchecked 1
- 10.6019/CHEMBL5060014 Transcription intermediary factor 1-alpha 1

Data from ChEMBL 36 via Core Engine