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Compound Detail

CHEMBL14276

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COc1cc2c(cc1C(F)(F)F)N(C(=O)Nc1cc(F)cc(-c3cccnc3)c1)CC2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL14276
Phase Preclinical
Structure Type MOL
InChI Key RRJLJKRFFRZRAF-UHFFFAOYSA-N
8
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

431.4
MW (Da)
5.51
ALogP
3
HBA
1
HBD
54.5
PSA (Ų)
0.56
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H17F4N3O2
MW 431.39
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.63

Activity Summary

IC50 14 meas. best 8.0
Ki 3 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 9.0 9.0 1.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 8.0 8.0 10.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
 IC50 8.0 8.0 10.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
 Ki 6.9 6.9 125.9 1
Plasmodium falciparum
CHEMBL364
 IC50 6.37 5.76 430.0 9
Cytochrome P450 3A4
CHEMBL340
 IC50 5.05 5.05 9000.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 4.68 4.68 21000.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.55 4.55 28000.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.09 4.09 82000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2C Ki = 1.0 nM 9.0 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2C in HEK293 ... 10737744
5-hydroxytryptamine receptor 2C IC50 = 10.0 nM 8.0 Inhibition of human 5HT2c receptor expressed in CHO-K1 cells assessed as inhibit... 24900481
5-hydroxytryptamine receptor 2B Ki = 10.0 nM 8.0 Binding affinities towards human cloned 5-hydroxytryptamine 2B receptor in HEK29... 10737744
5-hydroxytryptamine receptor 2A Ki = 125.89 nM 6.9 Binding affinity towards human cloned 5-hydroxytryptamine receptor 2A in HEK293 ... 10737744
Plasmodium falciparum IC50 = 430.0 nM 6.37 Antiplasmodial activity against Plasmodium falciparum 3D7A assessed as inhibitio... 24900481
Plasmodium falciparum IC50 = 1000.0 nM 6.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1584.89 nM 5.8 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1584.89 nM 5.8 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1584.89 nM 5.8 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 1995.26 nM 5.7 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 2120.0 nM 5.67 Antiplasmodial activity against Plasmodium falciparum Dd2 assessed as inhibition... 24900481
Plasmodium falciparum IC50 = 2511.89 nM 5.6 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Cytochrome P450 3A4 IC50 = 9000.0 nM 5.05 Inhibition of heterologously expressed human cytochrome P450 3A4 10737744
Cytochrome P450 2D6 IC50 = 21000.0 nM 4.68 Inhibition of heterologously expressed human cytochrome P450 2D6 10737744
Cytochrome P450 1A2 IC50 = 28000.0 nM 4.55 Inhibition of heterologously expressed human cytochrome P450 1A2. 10737744
Cytochrome P450 2C9 IC50 = 82000.0 nM 4.09 Inhibition of heterologously expressed human cytochrome P450 2C9 10737744

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
24900481 10.1021/ml300008j Plasmodium falciparum 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
10737744 10.1021/jm990388c Cytochrome P450 3A4 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
24900481 10.1021/ml300008j 5-hydroxytryptamine receptor 2C 1
24900481 10.1021/ml300008j Unchecked 1
17417631 10.1038/nchembio873 Unchecked 1
10737744 10.1021/jm990388c 5-hydroxytryptamine receptor 2A 1
10737744 10.1021/jm990388c Cytochrome P450 2D6 1
10737744 10.1021/jm990388c Cytochrome P450 2C19 1
10737744 10.1021/jm990388c Cytochrome P450 2C9 1
10737744 10.1021/jm990388c Rattus norvegicus 1
10737744 10.1021/jm990388c Cytochrome P450 1A2 1
10737744 10.1021/jm990388c Serotonin receptor (2b and 2c) 1
10737744 10.1021/jm990388c Serotonin 2 receptors; 5-HT2a & 5-HT2c 1
10737744 10.1021/jm990388c 5-hydroxytryptamine receptor 2C 1
10737744 10.1021/jm990388c 5-hydroxytryptamine receptor 2B 1

Data from ChEMBL 36 via Core Engine