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Compound Detail

CHEMBL33899

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

Basic Information

ChEMBL ID CHEMBL33899
Phase Preclinical
Structure Type MOL
InChI Key HJQQVNIORAQATK-DDJBQNAASA-N
6
Targets
17
Activities
2
Assay Types
10
PK Parameters
20
Publications
0
Known Names

Molecular Properties

354.4
MW (Da)
6.15
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.43
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 C25H22O2
MW 354.45
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness 0.23

Activity Summary

IC50 13 meas. best 8.59
EC50 4 meas. best 7.24

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 IC50 8.59 6.6788 2.6 8
Estrogen receptor beta
CHEMBL242
 IC50 7.25 7.25 56.0 1
Ishikawa
CHEMBL614649
 EC50 7.24 7.24 58.0 1
Unchecked
CHEMBL612545
 IC50 6.58 6.58 260.0 1
MCF7
CHEMBL387
 IC50 6.53 6.27 295.1 2
MCF7
CHEMBL387
 EC50 6.52 6.52 300.0 1
Estrogen receptor
CHEMBL206
 EC50 6.41 6.41 390.0 2
Progesterone receptor
CHEMBL208
 IC50 5.4 5.4 3981.1 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 137000.0 ng.hr.mL-1 Mus musculus
CL 31.62 mL.min-1.g-1 Homo sapiens
CL 107.15 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 6.2 mL.min-1.kg-1 Mus musculus
CL 80.0 mL.min-1.kg-1 Rattus norvegicus
F 62.0 % Mus musculus
F 68.0 % Rattus norvegicus
Fu 0.002 - Homo sapiens
Fu 0.064 - Mus musculus
Fu 0.0001 - Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor IC50 = 2.6 nM 8.59 Inhibition of Fluormone-ES2 binding affinity to ERalpha (unknown origin) after 2... 31129450
Estrogen receptor IC50 = 3.236 nM 8.49 Binding affinity to ERalpha receptor (unknown origin) 26407012
Estrogen receptor IC50 = 39.0 nM 7.41 Displacement of [3H]17-beta-estradiol from human Estrogen receptor alpha 10673099
Estrogen receptor beta IC50 = 56.0 nM 7.25 Displacement of [3H]17-beta-estradiol from human Estrogen receptor beta 10673099
Ishikawa EC50 = 58.0 nM 7.24 Concentration of compound required to induce 50 % of the maximum stimulation of ... 8201587
Estrogen receptor IC50 = 264.0 nM 6.58 Induction of ERalpha degradation in human MCF7 cells after 18 to 24 hrs by Weste... 28296398
Unchecked IC50 = 260.0 nM 6.58 Displacement of [3H]-estradiol from recombinant human N-terminal His-tagged ERal... 28296398
MCF7 IC50 = 295.12 nM 6.53 Antiproliferative activity against human MCF7 cells 26407012
MCF7 EC50 = 300.0 nM 6.52 Inhibition of cell proliferation in human MCF7 cells after 7 days by laser scann... 25790336
Estrogen receptor EC50 = 390.0 nM 6.41 Induction of ERalpha degradation in human MCF7 cells in phenol red free RPMI med... 30587451
Estrogen receptor EC50 = 390.0 nM 6.41 Induction of estrogen receptor-alpha degradation in human MCF7 cells after 4 hrs... 25879485
Estrogen receptor IC50 = 654.0 nM 6.18 Antagonist effect on transcriptional activation in MCF-7 cells expressing estrog... 10673099
MCF7 IC50 = 985.0 nM 6.01 Cytotoxicity against human MCF7 cells assessed as cell viability after 5 days by... 25879485
Estrogen receptor IC50 = 1288.25 nM 5.89 Antagonist activity at ERalpha receptor in human MCF7 cells 26407012
Estrogen receptor IC50 = 4000.0 nM 5.4 Antagonist activity at ER alpha in human MCF7 cells assessed as inhibition of es... 25790336
Progesterone receptor IC50 = 3981.07 nM 5.4 Antagonist activity at progesterone receptor in human MCF cells assessed as estr... 26407012
Estrogen receptor IC50 = 12825.0 nM 4.89 Antagonist activity at ERalpha in human MCF7 cells assessed as inhibition of est... 28296398

Literature References

PubMed DOI Target Context # Activities
25879485 10.1021/acs.jmedchem.5b00054 Liver microsome 15
25879485 10.1021/acs.jmedchem.5b00054 ADMET 5
25790336 10.1021/acs.jmedchem.5b00066 Estrogen receptor 4
- 10.6019/CHEMBL3301361 ADMET 3
25879485 10.1021/acs.jmedchem.5b00054 Estrogen receptor 3
26407012 10.1021/acs.jmedchem.5b00984 Progesterone receptor 3
28296398 10.1021/acs.jmedchem.6b01468 Estrogen receptor 3
25790336 10.1021/acs.jmedchem.5b00066 Plasma 3
10673099 10.1016/s0960-894x(99)00648-4 Estrogen receptor 3
25790336 10.1021/acs.jmedchem.5b00066 Mus musculus 3
25790336 10.1021/acs.jmedchem.5b00066 Rattus norvegicus 3
30587451 10.1016/j.bmcl.2018.12.042 Estrogen receptor 2
25879485 10.1021/acs.jmedchem.5b00054 MCF7 2
25790336 10.1021/acs.jmedchem.5b00066 No relevant target 2
- 10.6019/CHEMBL3301361 No relevant target 2
8201587 10.1021/jm00037a002 Ishikawa 2
26407012 10.1021/acs.jmedchem.5b00984 Estrogen receptor 2
31129450 10.1016/j.ejmech.2019.05.023 Estrogen receptor 1
25790336 10.1021/acs.jmedchem.5b00066 Voltage-gated inwardly rectifying potassium channel KCNH2 1
25790336 10.1021/acs.jmedchem.5b00066 MCF7 1

Data from ChEMBL 36 via Core Engine