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Compound Detail

CHEMBL418971

BISPHENOL A
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CC(C)(c1ccc(O)cc1)c1ccc(O)cc1

Basic Information

ChEMBL ID CHEMBL418971
Name BISPHENOL A
Phase Preclinical
Structure Type MOL
InChI Key IISBACLAFKSPIT-UHFFFAOYSA-N
15
Targets
39
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

228.3
MW (Da)
3.42
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.83
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C15H16O2
MW 228.29
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness 0.07

Activity Summary

IC50 25 meas. best 8.31
Ki 6 meas. best 6.19
EC50 5 meas. best 6.54
Kd 3 meas. best 8.26

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen-related receptor gamma
CHEMBL4245
IC50 8.31 8.31 4.9 1
Estrogen-related receptor gamma
CHEMBL4245
Kd 8.26 8.26 5.5 1
Estrogen receptor
CHEMBL206
EC50 6.54 6.1367 290.0 3
Estrogen receptor
CHEMBL206
IC50 6.31 6.0725 490.0 4
Estrogen receptor
CHEMBL206
Ki 6.19 6.19 649.0 1
Estrogen receptor beta
CHEMBL242
IC50 6.17 6.115 670.0 2
Estrogen receptor beta
CHEMBL242
EC50 6.12 6.04 757.0 2
Polyunsaturated fatty acid lipoxygenase ALOX15
CHEMBL4358
IC50 5.88 5.88 1304.0 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2
CHEMBL3585237
IC50 5.7 5.7 2000.0 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL4693
IC50 5.7 5.7 2000.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 5.6 5.6 2516.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 5.27 5.27 5420.0 1
Androgen receptor
CHEMBL1871
IC50 5.23 5.23 5900.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 4.97 4.97 10798.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 4.82 4.82 15108.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 4.78 4.78 16483.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 4.78 4.78 16620.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 4.72 4.72 19015.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 4.69 4.69 20325.0 1
Androgen receptor
CHEMBL3072
Ki 4.65 4.65 22531.0 1
Androgen receptor
CHEMBL3072
IC50 4.47 4.3 33796.0 2
Voltage-dependent L-type calcium channel subunit alpha-1C
CHEMBL2529
IC50 4.46 4.46 35000.0 1
Voltage-dependent N-type calcium channel subunit alpha-1B
CHEMBL3637936
IC50 4.46 4.46 35000.0 1
HT-22
CHEMBL614316
IC50 4.01 4.01 97000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen-related receptor gamma IC50 = 4.91 nM 8.31 Binding affinity to human ERRgamma 28882502
Estrogen-related receptor gamma Kd = 5.5 nM 8.26 Binding affinity to human ERR gamma -
Estrogen receptor EC50 = 290.0 nM 6.54 Agonist activity at estrogen receptor in human MCF7 cells assessed as ERE-mediat... 26905830
Estrogen receptor IC50 = 490.0 nM 6.31 Competitive Binding Assay: Competitive binding assays were performed by incubati... -
Estrogen receptor IC50 = 504.0 nM 6.3 Binding affinity to GST-tagged human ER alpha ligand-binding domain by TR-FRET a... 30940565
Estrogen receptor Ki = 649.0 nM 6.19 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
Estrogen receptor beta IC50 = 670.0 nM 6.17 Competitive Binding Assay: Competitive binding assays were performed by incubati... -
Estrogen receptor beta EC50 = 757.0 nM 6.12 Agonist activity at ERbeta (unknown origin) expressed in human HeLa cells assess... 31879182
Estrogen receptor EC50 = 797.0 nM 6.1 Agonist activity at ERalpha (unknown origin) expressed in human HeLa cells asses... 31879182
Estrogen receptor beta IC50 = 870.0 nM 6.06 Displacement of [3H]17-beta estradiol from GST-fused human recombinant ERbeta li... 31879182
Estrogen receptor IC50 = 904.0 nM 6.04 Displacement of [3H]17-beta estradiol from GST-fused human recombinant ERalpha l... 31879182
Estrogen receptor beta EC50 = 1100.0 nM 5.96 Agonist activity at human Gal4-ERbeta by reporter gene assay 23768907
Polyunsaturated fatty acid lipoxygenase ALOX15 IC50 = 1304.0 nM 5.88 DRUGMATRIX: Lipoxygenase 15-LO enzyme inhibition (substrate: Linoleic acid) -
Estrogen receptor EC50 = 1689.0 nM 5.77 Selective estrogen receptor down-regulator activity at FLAG-tagged ERalpha (unkn... 30940565
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 IC50 = 2000.0 nM 5.7 Inhibition of rabbit skeletal muscle microsomes SERCA1a by enzyme-coupled method 32030976
Sarcoplasmic/endoplasmic reticulum calcium ATPase 2 IC50 = 2000.0 nM 5.7 Inhibition of rat cerebellar microsomes SERCA2b by enzyme-coupled method 32030976
Estrogen receptor IC50 = 2271.0 nM 5.64 DRUGMATRIX: Estrogen ERalpha radioligand binding (ligand: [3H] Estradiol) -
5-hydroxytryptamine receptor 6 Ki = 2516.0 nM 5.6 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
5-hydroxytryptamine receptor 6 IC50 = 5420.0 nM 5.27 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
Androgen receptor IC50 = 5900.0 nM 5.23 Antagonist activity at human pSG5-AR assessed as inhibition of dihydrotestostero... 23768907

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 864
- 10.6019/CHEMBL5724801 U2OS 320
- 10.6019/CHEMBL5724801 Fibroblast 320
- 10.6019/CHEMBL5724801 HEK-293T 320
- 10.6019/CHEMBL5303304 Fibroblast 5
30940565 10.1016/j.bmc.2019.03.042 Estrogen receptor 5
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
31879182 10.1016/j.bmc.2019.115274 Estrogen receptor beta 3
23768907 10.1016/j.bmcl.2013.05.067 Estrogen receptor 2
32030976 10.1021/acs.jmedchem.9b01509 Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 2
24630694 10.1016/j.bmc.2014.02.025 Estrogen receptor 2
- 10.6019/CHEMBL5303304 U2OS 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
24266771 10.1021/jm401291q GTPase KRas 2
24266771 10.1021/jm401291q GTP-binding protein Rheb 2
23768907 10.1016/j.bmcl.2013.05.067 Estrogen receptor beta 2
21353727 10.1016/j.ejmech.2011.01.069 Unchecked 2
31879182 10.1016/j.bmc.2019.115274 Estrogen receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
9288164 10.1021/jm970023x B16 2

Data from ChEMBL 36 via Core Engine