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Compound Detail

CHEMBL4448852

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C[C@@H]1Cc2c(ccc3[nH]ncc23)[C@@H](c2c(F)cc(/C=C/C(=O)O)cc2F)N1CC(C)(C)F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4448852
Phase Preclinical
Structure Type MOL
InChI Key DAENOLUGFUWJQG-ZAKKQHHBSA-N
4
Targets
9
Activities
1
Assay Types
12
PK Parameters
11
Publications
0
Known Names

Molecular Properties

443.5
MW (Da)
5.02
ALogP
3
HBA
2
HBD
69.2
PSA (Ų)
0.54
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H24F3N3O2
MW 443.47
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.35

Activity Summary

IC50 9 meas. best 10.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
G-protein coupled estrogen receptor 1
CHEMBL5872
 IC50 10.4 10.4 0.0 1
Estrogen receptor
CHEMBL206
 IC50 9.6 9.15 0.3 6
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.6 5.6 2500.0 1
Cytochrome P450 3A4
CHEMBL340
 IC50 4.89 4.89 13000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 368.08 ng.hr.mL-1 Rattus norvegicus
AUC 1419.1 ng.hr.mL-1 Canis lupus familiaris
CL 23.0 mL.min-1.kg-1 Rattus norvegicus
CL 5.9 mL.min-1.kg-1 Canis lupus familiaris
F 31.0 % Rattus norvegicus
F 45.0 % Canis lupus familiaris
Fu 0.0083 - Rattus norvegicus
Fu 0.0058 - Homo sapiens
Fu 0.0095 - Mus musculus
Fu 0.0032 - Canis lupus familiaris
T1/2 1.2 hr Rattus norvegicus
T1/2 6.1 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
G-protein coupled estrogen receptor 1 IC50 = 0.04 nM 10.4 Biological Assay: The compounds of the present invention have an inhibition effe... -
Estrogen receptor IC50 = 0.2512 nM 9.6 Induction of ERalpha degradation in human MCF7 cells after 18 to 24 hrs by in mu... 30640465
Estrogen receptor IC50 = 0.2512 nM 9.6 Induction of ERalpha degradation in human MCF7 cells assessed as reduction in ER... 30640465
Estrogen receptor IC50 = 0.3162 nM 9.5 Binding affinity to recombinant human GST-tagged ERalpha LBD expressed in baculo... 30640465
Estrogen receptor IC50 = 0.7943 nM 9.1 Induction of ERalpha degradation in human MCF7 cells assessed as reduction in ER... 30640465
Estrogen receptor IC50 = 1.0 nM 9.0 Antagonist activity at ERalpha in human MCF7 cells assessed as inhibition of est... 30640465
Estrogen receptor IC50 = 7.943 nM 8.1 Induction of ERalpha degradation in human MCF7 cells assessed as reduction in ER... 30640465
Cytochrome P450 2C9 IC50 = 2500.0 nM 5.6 Inhibition of CYP2C9 in human liver microsomes 30640465
Cytochrome P450 3A4 IC50 = 13000.0 nM 4.89 Inhibition of CYP3A4 in human liver microsomes 30640465

Literature References

PubMed DOI Target Context # Activities
30640465 10.1021/acs.jmedchem.8b01837 ADMET 23
30640465 10.1021/acs.jmedchem.8b01837 Estrogen receptor 9
30640465 10.1021/acs.jmedchem.8b01837 No relevant target 4
30640465 10.1021/acs.jmedchem.8b01837 Mus musculus 3
30640465 10.1021/acs.jmedchem.8b01837 MCF7 1
30640465 10.1021/acs.jmedchem.8b01837 Cytochrome P450 2C9 1
30640465 10.1021/acs.jmedchem.8b01837 Cytochrome P450 3A4 1
30640465 10.1021/acs.jmedchem.8b01837 Voltage-gated inwardly rectifying potassium channel KCNH2 1
30640465 10.1021/acs.jmedchem.8b01837 Cytochrome P450 1A2 1
30640465 10.1021/acs.jmedchem.8b01837 Cytochrome P450 2C19 1
30640465 10.1021/acs.jmedchem.8b01837 Cytochrome P450 2D6 1

Data from ChEMBL 36 via Core Engine