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Compound Detail

CHEMBL5426983

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Cc1c(OCCNCCCF)ncc(F)c1[C@@H]1c2[nH]c3ccccc3c2C[C@@H](C)N1C[C@@H](C)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5426983
Phase Preclinical
Structure Type MOL
InChI Key JMHAEPDWKOSCPH-RYUVBPIJSA-N
5
Targets
15
Activities
2
Assay Types
23
PK Parameters
14
Publications
0
Known Names

Molecular Properties

500.6
MW (Da)
4.40
ALogP
5
HBA
3
HBD
90.5
PSA (Ų)
0.34
QED
1
Ro5 Violations
11
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H34F2N4O3
MW 500.59
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -0.32

Activity Summary

IC50 13 meas. best 9.8
Ki 2 meas. best 5.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Estrogen receptor
CHEMBL206
 IC50 9.8 8.8913 0.2 8
Unchecked
CHEMBL612545
 IC50 8.9 8.35 1.3 2
MCF7
CHEMBL387
 IC50 8.2 7.8 6.3 2
Estrogen receptor beta
CHEMBL242
 IC50 7.7 7.7 19.9 1
Unchecked
CHEMBL612545
 Ki 5.33 5.33 4700.0 1
Urotensin-2 receptor
CHEMBL3764
 Ki 5.11 5.11 7700.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 21.0 uL/min Rattus norvegicus
CL 2.0 uL/min Canis lupus familiaris
CL 2.4 uL/min Macaca mulatta
CL 30.0 mL.min-1.kg-1 Mus musculus
CL 58.0 mL.min-1.kg-1 Rattus norvegicus
CL 4.0 mL.min-1.kg-1 Canis lupus familiaris
CL 1.1 mL.min-1.kg-1 Macaca mulatta
F 45.0 % Mus musculus
F 19.0 % Rattus norvegicus
F 80.0 % Canis lupus familiaris
F 30.0 % Macaca mulatta
Fu 0.22 - Homo sapiens
Fu 0.26 - Mus musculus
Fu 0.37 - Rattus norvegicus
Fu 0.2 - Canis lupus familiaris
Fu 0.26 - Mus musculus
Fu 0.37 - Rattus norvegicus
Fu 0.2 - Canis lupus familiaris
Fu 0.44 - Macaca mulatta
T1/2 3.0 hr Mus musculus
T1/2 0.8 hr Rattus norvegicus
T1/2 63.0 hr Canis lupus familiaris
T1/2 1.2 hr Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Estrogen receptor IC50 = 0.1585 nM 9.8 Induction of ERalpha degradation in human MCF7 cells assessed as downregulation ... 36727211
Estrogen receptor IC50 = 0.3981 nM 9.4 Induction of ERalpha degradation in human MCF7 cells assessed as downregulation ... 36727211
Estrogen receptor IC50 = 0.49 nM 9.31 MCF-7 ER Down-Regulation Assay: The ability of compounds to down-regulate Estrog... -
Unchecked IC50 = 1.259 nM 8.9 Induction of ERbeta degradation in human MCF7 cells assessed as inhibition of es... 36727211
Estrogen receptor IC50 = 1.585 nM 8.8 Binding affinity to ERalpha (unknown origin) by LanthaScreen TR-FRET competitive... 36727211
Estrogen receptor IC50 = 1.8 nM 8.74 ERalpha Binding Assay: The ability of compounds to bind to isolated Estrogen Rec... -
Estrogen receptor IC50 = 1.8 nM 8.74 Binding Assay: ERα: The ability of compounds to bind to isolated Estrogen Recept... -
Estrogen receptor IC50 = 1.8 nM 8.74 ERalpha Binding Assay: The ability of compounds to bind to isolated Estrogen Rec... -
MCF7 IC50 = 6.31 nM 8.2 Antiproliferative activity against human MCF7 cells assessed as reduction in est... 36727211
Unchecked IC50 = 15.85 nM 7.8 Induction of ERbeta degradation in human MCF7 cells harbouring Y537S mutant asse... 36727211
Estrogen receptor beta IC50 = 19.95 nM 7.7 Binding affinity to ERbeta (unknown origin) by LanthaScreen TR-FRET competitive ... 36727211
Estrogen receptor IC50 = 25.12 nM 7.6 Induction of ERalpha degradation in human MCF7 cells assessed as reduction in po... 36727211
MCF7 IC50 = 39.81 nM 7.4 Antiproliferative activity against human MCF7 cells harbouring Y537S mutant asse... 36727211
Unchecked Ki = 4700.0 nM 5.33 Binding affinity to diltiazem site of calcium channel (unknown origin) 36727211
Urotensin-2 receptor Ki = 7700.0 nM 5.11 Binding affinity to urotensin 2 receptor (unknown origin) 36727211

Literature References

PubMed DOI Target Context # Activities
36727211 10.1021/acs.jmedchem.2c01964 ADMET 36
36727211 10.1021/acs.jmedchem.2c01964 Estrogen receptor 15
36727211 10.1021/acs.jmedchem.2c01964 Breast carcinoma cell 5
36727211 10.1021/acs.jmedchem.2c01964 Unchecked 4
36727211 10.1021/acs.jmedchem.2c01964 No relevant target 3
36727211 10.1021/acs.jmedchem.2c01964 MCF7 2
36727211 10.1021/acs.jmedchem.2c01964 Estrogen receptor beta 2
36727211 10.1021/acs.jmedchem.2c01964 Voltage-gated inwardly rectifying potassium channel KCNH2 1
36727211 10.1021/acs.jmedchem.2c01964 Cytochrome P450 1A2 1
36727211 10.1021/acs.jmedchem.2c01964 Cytochrome P450 2C19 1
36727211 10.1021/acs.jmedchem.2c01964 Cytochrome P450 2C9 1
36727211 10.1021/acs.jmedchem.2c01964 Cytochrome P450 2D6 1
36727211 10.1021/acs.jmedchem.2c01964 Cytochrome P450 3A4 1
36727211 10.1021/acs.jmedchem.2c01964 Urotensin-2 receptor 1

Data from ChEMBL 36 via Core Engine