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Compound Detail

CHEMBL195515

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CC/C(=C(\c1ccc(O)cc1)c1ccc(/C=C/C(=O)O)cc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL195515
Phase Preclinical
Structure Type MOL
InChI Key SCVIEONTACSLJA-YGCRUXFTSA-N

Known Names

GW7604
6
Targets
25
Activities
3
Assay Types
4
PK Parameters
20
Publications
1
Known Names

Molecular Properties

370.4
MW (Da)
5.86
ALogP
2
HBA
2
HBD
57.5
PSA (Ų)
0.42
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H22O3
MW 370.45
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness 0.37

Activity Summary

IC50 20 meas. best 9.84
Ki 3 meas. best 8.6
EC50 2 meas. best 8.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 IC50 9.84 8.1045 0.1 11
Estrogen receptor
CHEMBL2093866
 IC50 8.9 8.9 1.3 1
Estrogen receptor
CHEMBL206
 EC50 8.77 8.77 1.7 2
Estrogen receptor
CHEMBL206
 Ki 8.6 8.085 2.5 2
Estrogen receptor beta
CHEMBL242
 IC50 8.52 7.9167 3.0 3
MCF7
CHEMBL387
 IC50 8.34 8.32 4.6 2
Unchecked
CHEMBL612545
 IC50 8.04 7.895 9.2 2
Estrogen receptor beta
CHEMBL242
 Ki 8.0 8.0 10.0 1
Progesterone receptor
CHEMBL208
 IC50 7.92 7.92 12.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 13000.0 ng.hr.mL-1 Mus musculus
AUC 228.2 ng/g.hr Mus musculus
AUC 169.3 ng/g.hr Mus musculus
Fu 0.0009 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor IC50 = 0.1445 nM 9.84 Binding affinity to ERalpha receptor (unknown origin) 26407012
Estrogen receptor IC50 = 0.15 nM 9.82 Binding affinity to ER alpha (unknown origin) by LanthaScreen TR-FRET competitiv... 25790336
Estrogen receptor IC50 = 1.259 nM 8.9 pIC50 for 1 nM estradiol-induced Ishikawa cell proliferation 15771467
Estrogen receptor EC50 = 1.7 nM 8.77 Induction of ERalpha degradation in human MCF7 cells in phenol red free RPMI med... 30587451
Estrogen receptor EC50 = 1.7 nM 8.77 Induction of estrogen receptor-alpha degradation in human MCF7 cells after 4 hrs... 25879485
Estrogen receptor Ki = 2.512 nM 8.6 Binding affinity for human estrogen receptor alpha 15771467
Estrogen receptor beta IC50 = 3.0 nM 8.52 Displacement of [3H]-E2 from estrogen receptor-beta (unknown origin) by scintill... 25879485
Estrogen receptor beta IC50 = 3.77 nM 8.42 Displacement of fluorescent-labelled E2 from recombinant human GST-tagged ERbeta... 32169784
MCF7 IC50 = 4.6 nM 8.34 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 30587451
MCF7 IC50 = 5.0 nM 8.3 Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by... 25879485
Estrogen receptor IC50 = 5.35 nM 8.27 Displacement of fluorescent-labelled E2 from recombinant human GST-tagged ERalph... 32169784
Estrogen receptor IC50 = 6.0 nM 8.22 Displacement of [3H]-E2 from estrogen receptor-alpha (unknown origin) by scintil... 25879485
Estrogen receptor IC50 = 6.761 nM 8.17 Antagonist activity at ERalpha receptor in human MCF7 cells 26407012
Estrogen receptor IC50 = 7.0 nM 8.15 Suppression of ER alpha in human MCF7 cells after 24 hrs by immunostaining analy... 25790336
Estrogen receptor IC50 = 7.0 nM 8.15 Induction of ERalpha degradation in human MCF7 cells after 18 to 24 hrs by Weste... 28296398
Unchecked IC50 = 9.2 nM 8.04 Displacement of [3H]-estradiol from recombinant human N-terminal His-tagged ERal... 28296398
Estrogen receptor beta Ki = 10.0 nM 8.0 Binding affinity for human estrogen receptor beta 15771467
Estrogen receptor IC50 = 12.0 nM 7.92 Antagonist activity at ER alpha in human MCF7 cells assessed as inhibition of es... 25790336
Progesterone receptor IC50 = 12.02 nM 7.92 Antagonist activity at progesterone receptor in human MCF cells assessed as estr... 26407012
Unchecked IC50 = 18.0 nM 7.75 Antagonist activity at estrogen receptor in human MCF7 cells assessed as inhibit... 25879485

Literature References

PubMed DOI Target Context # Activities
32169784 10.1016/j.ejmech.2020.112191 Estrogen receptor 6
32169784 10.1016/j.ejmech.2020.112191 Estrogen receptor beta 5
25790336 10.1021/acs.jmedchem.5b00066 Estrogen receptor 4
25879485 10.1021/acs.jmedchem.5b00054 Estrogen receptor 4
15771467 10.1021/jm040154f Estrogen receptor 4
32787092 10.1021/acs.jmedchem.0c00868 ADMET 3
28296398 10.1021/acs.jmedchem.6b01468 Estrogen receptor 3
26407012 10.1021/acs.jmedchem.5b00984 Progesterone receptor 3
30587451 10.1016/j.bmcl.2018.12.042 Estrogen receptor 2
25879485 10.1021/acs.jmedchem.5b00054 MCF7 2
26407012 10.1021/acs.jmedchem.5b00984 Estrogen receptor 2
32169784 10.1016/j.ejmech.2020.112191 MCF7 2
25879485 10.1021/acs.jmedchem.5b00054 Estrogen receptor beta 1
28296398 10.1021/acs.jmedchem.6b01468 Unchecked 1
25879485 10.1021/acs.jmedchem.5b00054 Unchecked 1
25879485 10.1021/acs.jmedchem.5b00054 Mus musculus 1
25790336 10.1021/acs.jmedchem.5b00066 Hepatocyte 1
25790336 10.1021/acs.jmedchem.5b00066 Plasma 1
25790336 10.1021/acs.jmedchem.5b00066 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37163948 10.1016/j.ejmech.2023.115422 Estrogen receptor 1

Data from ChEMBL 36 via Core Engine