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Compound Detail

CHEMBL149791

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CCC(=C(c1ccc(O)cc1)c1ccc(O)cc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL149791
Phase Preclinical
Structure Type MOL
InChI Key BPKSDMHGDYTXLI-UHFFFAOYSA-N
4
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

316.4
MW (Da)
5.47
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.63
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H20O2
MW 316.40
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness 0.20

Activity Summary

EC50 6 meas. best 10.82
IC50 6 meas. best 10.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 EC50 10.82 9.91 0.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 10.3 10.3 0.1 1
Estrogen receptor
CHEMBL206
 IC50 10.22 8.84 0.1 3
Estrogen receptor beta
CHEMBL242
 EC50 6.51 6.51 306.9 3
Aromatase
CHEMBL1978
 IC50 4.6 4.6 24880.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor EC50 = 0.015 nM 10.82 Agonist activity at ER in human MCF7:WS8 cells assessed as increase in cell grow... 24805199
NON-PROTEIN TARGET EC50 = 0.05 nM 10.3 Estrogenic activity in human ERalpha expressing MCF7:WS8 cells assessed as stimu... 20334368
Estrogen receptor IC50 = 0.06 nM 10.22 Binding affinity to GST-tagged human ER alpha ligand-binding domain by TR-FRET a... 30940565
Estrogen receptor EC50 = 1.0 nM 9.0 Selective estrogen receptor down-regulator activity at FLAG-tagged ERalpha (unkn... 30940565
Estrogen receptor IC50 = 3.3 nM 8.48 Antagonist activity at FLAG-tagged ERalpha (unknown origin) expressed in HEK293 ... 30940565
Estrogen receptor IC50 = 15.0 nM 7.82 Antiestrogenic activity in MCF-7-2a cells as concentration required to reduce es... 12431063
Estrogen receptor beta EC50 = 306.9 nM 6.51 Displacement of fluorescent ES2 from human recombinant ERbeta after 2 hrs by flu... 23731360
Estrogen receptor beta EC50 = 306.9 nM 6.51 Displacement of fluorescent ES2 from recombinant human ERbeta after 2 hrs in abs... 27647367
Estrogen receptor beta EC50 = 307.0 nM 6.51 Displacement of ES2 from recombinant human ER-beta incubated for 2 hrs by fluore... 26704594
Aromatase IC50 = 24880.0 nM 4.6 Inhibition of human recombinant microsomal aromatase-mediated 7-methoxy-4-triflu... 23731360
Aromatase IC50 = 24880.0 nM 4.6 Inhibition of recombinant human microsomal CYP19 using MFC as substrate measured... 27647367
Aromatase IC50 = 24900.0 nM 4.6 Inhibition of recombinant human aromatase incubated for 30 mins using fluorometr... 26704594

Literature References

PubMed DOI Target Context # Activities
24805199 10.1021/jm500569h Estrogen receptor 8
30940565 10.1016/j.bmc.2019.03.042 Estrogen receptor 5
12431063 10.1021/jm0209230 Estrogen receptor 3
20334368 10.1021/jm901907u Estrogen receptor 3
26704594 10.1021/acs.jmedchem.5b01677 Estrogen receptor beta 2
27647367 10.1016/j.bmc.2016.08.064 Aromatase 2
23731360 10.1021/jm400364h Aromatase 2
20334372 10.1021/jm100047k Estrogen receptor beta 1
20334372 10.1021/jm100047k Estrogen receptor 1
20334368 10.1021/jm901907u NON-PROTEIN TARGET 1
20334372 10.1021/jm100047k Unchecked 1
15943467 10.1021/jm050251o No relevant target 1
23731360 10.1021/jm400364h Estrogen receptor 1
23731360 10.1021/jm400364h Estrogen receptor beta 1
15943467 10.1021/jm050251o Estrogen receptor beta 1
24805199 10.1021/jm500569h Unchecked 1
27647367 10.1016/j.bmc.2016.08.064 Estrogen receptor 1
15943467 10.1021/jm050251o Unchecked 1
27647367 10.1016/j.bmc.2016.08.064 Estrogen receptor beta 1
15943467 10.1021/jm050251o Estrogen receptor 1

Data from ChEMBL 36 via Core Engine