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Compound Detail

CHEMBL4447340

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CC1=C(c2cccc(O)c2)[C@H](c2ccc(OCCN3CC(CF)C3)cc2)Oc2ccc(O)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4447340
Phase Preclinical
Structure Type MOL
InChI Key KJAAPZIFCQQQKX-NDEPHWFRSA-N
7
Targets
18
Activities
2
Assay Types
25
PK Parameters
20
Publications
0
Known Names

Molecular Properties

461.5
MW (Da)
5.44
ALogP
5
HBA
2
HBD
62.2
PSA (Ų)
0.49
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H28FNO4
MW 461.53
Aromatic Rings 3
Heavy Atoms 34
NP-Likeness 0.03

Activity Summary

IC50 16 meas. best 10.52
EC50 2 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 IC50 10.52 10.1413 0.0 8
MCF7
CHEMBL387
 IC50 10.0 9.74 0.1 3
T47D
CHEMBL614361
 IC50 9.54 9.54 0.3 1
MCF7
CHEMBL387
 EC50 9.52 9.52 0.3 2
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 6.41 6.41 390.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 5.52 5.52 3000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.5 5.5 3200.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.34 5.34 4600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 6900.0 ng.hr.mL-1 Mus musculus
AUC 160.0 ng.hr.mL-1 Rattus norvegicus
CL 60.0 mL.min-1.kg-1 Rattus norvegicus
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 45.0 mL.min-1.kg-1 Rattus norvegicus
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 45.0 mL.min-1.kg-1 Rattus norvegicus
CL 100.0 mL.min-1.kg-1 Rattus norvegicus
CL 85.0 mL.min-1.kg-1 Rattus norvegicus
CL 81.0 mL.min-1.kg-1 Rattus norvegicus
CL 24.0 mL.min-1.kg-1 Canis lupus familiaris
CL 17.0 mL.min-1.kg-1 Macaca fascicularis
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 46.0 mL.min-1.kg-1 Rattus norvegicus
CL 85.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 2058.37 nM Mus musculus
F 10.0 % Rattus norvegicus
F 10.0 % Rattus norvegicus
F 16.0 % Rattus norvegicus
F 16.0 % Rattus norvegicus
F 23.0 % Canis lupus familiaris
F 5.0 % Macaca fascicularis
F 17.0 % Rattus norvegicus
Fu 0.00019 - Mus musculus
T1/2 6.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor IC50 = 0.03 nM 10.52 Induction of ERalpha degradation in human MCF7 cells after 4 hrs by FITC/Hoechst... 31311734
Estrogen receptor IC50 = 0.03 nM 10.52 Induction of ERalpha degradation in human MCF7 cells after 4 hrs by Alexafluor-4... 30732944
Estrogen receptor IC50 = 0.03 nM 10.52 Induction of ERalpha degradation in human MCF7 cells after 4 hrs by FITC/Hoechst... 32551022
Estrogen receptor IC50 = 0.07 nM 10.15 Breast Cancer Cell Viability Assay: MCF-7 cells were adjusted to a concentration... -
Estrogen receptor IC50 = 0.1 nM 10.0 Induction of ERalpha degradation in human MCF7 cells assessed as decrease in ERa... 30655946
MCF7 IC50 = 0.1 nM 10.0 Antiproliferative activity against human MCF7 cells after 5 days by CellTiter-Gl... 30655946
Estrogen receptor IC50 = 0.1 nM 10.0 Antagonist activity at estrogen receptor in human T47D cells incubated for 18 hr... 34251202
Estrogen receptor IC50 = 0.1 nM 10.0 Degradation of ER alpha in human MCF7 cells 35567964
MCF7 IC50 = 0.2 nM 9.7 Antiproliferative activity against human MCF7 cells after 3 days by CellTiter-Gl... 30732944
T47D IC50 = 0.29 nM 9.54 Antiproliferative activity against human T47D cells assessed as reduction in cel... 32551022
MCF7 EC50 = 0.3 nM 9.52 Antiproliferative activity against human MCF-7 cells incubated for 72 hrs by Cel... 34251202
MCF7 IC50 = 0.3 nM 9.52 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 32551022
MCF7 EC50 = 0.3 nM 9.52 Antiproliferative activity against human MCF7 cells after 72 hrs by Celltiter-Gl... 31311734
Estrogen receptor IC50 = 0.38 nM 9.42 Induction of ERalpha degradation in human T47D cells 32551022
Sodium-dependent dopamine transporter IC50 = 390.0 nM 6.41 Inhibition of dopamine transporter (unknown origin) 30655946
Cytochrome P450 2C8 IC50 = 3000.0 nM 5.52 Inhibition of CYP2C8 (unknown origin) 30655946
Cytochrome P450 2C9 IC50 = 3200.0 nM 5.5 Inhibition of CYP2C9 (unknown origin) 30655946
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 4600.0 nM 5.34 Inhibition of human ERG by patch clamp method 30655946

Literature References

PubMed DOI Target Context # Activities
30655946 10.1021/acsmedchemlett.8b00414 ADMET 10
31311734 10.1016/j.bmcl.2019.07.013 ADMET 8
32551022 10.1021/acsmedchemlett.0c00224 ADMET 6
34251202 10.1021/acs.jmedchem.1c00847 ADMET 5
32551022 10.1021/acsmedchemlett.0c00224 Estrogen receptor 5
34251202 10.1021/acs.jmedchem.1c00847 Unchecked 4
34251202 10.1021/acs.jmedchem.1c00847 Estrogen receptor 4
30655946 10.1021/acsmedchemlett.8b00414 Progesterone receptor 4
31746603 10.1021/acs.jmedchem.9b01580 T47D 3
30655946 10.1021/acsmedchemlett.8b00414 Estrogen receptor 3
34251202 10.1021/acs.jmedchem.1c00847 MCF7 2
30655946 10.1021/acsmedchemlett.8b00414 Mineralocorticoid receptor 2
30655946 10.1021/acsmedchemlett.8b00414 Glucocorticoid receptor 2
37377342 10.1021/acs.jmedchem.3c00136 Unchecked 2
34251202 10.1021/acs.jmedchem.1c00847 No relevant target 2
30655946 10.1021/acsmedchemlett.8b00414 MCF7 2
30732944 10.1016/j.bmcl.2019.01.036 Estrogen receptor 2
30655946 10.1021/acsmedchemlett.8b00414 Unchecked 2
31311734 10.1016/j.bmcl.2019.07.013 Estrogen receptor 2
30732944 10.1016/j.bmcl.2019.01.036 ADMET 2

Data from ChEMBL 36 via Core Engine