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Compound Detail

CHEMBL18331

PIRENPERONE
🧪 Phase II
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🧪 Phase II
Cc1nc2ccccn2c(=O)c1CCN1CCC(C(=O)c2ccc(F)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL18331
Name PIRENPERONE
Phase Phase II
Structure Type MOL
InChI Key HXCNRYXBZNHDNE-UHFFFAOYSA-N

Known Names

NSC-760095 Pirenperona Pirenperone R-47,465 R-47465
8
Targets
22
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names

Molecular Properties

393.5
MW (Da)
3.28
ALogP
5
HBA
0
HBD
54.7
PSA (Ų)
0.62
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral
USAN Stem -perone
USAN Year 1981

Extended Properties

Molecular Formula C23H24FN3O2
MW 393.46
Aromatic Rings 3
Heavy Atoms 29
NP-Likeness -1.87

Activity Summary

IC50 14 meas. best 8.74
Ki 7 meas. best 9.52
Kd 1 meas. best 5.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serotonin 2 (5-HT2) receptor
CHEMBL2093870
 Ki 9.52 9.26 0.3 2
Rattus norvegicus
CHEMBL376
 Ki 9.33 8.89 0.5 2
Rattus norvegicus
CHEMBL376
 IC50 8.74 8.445 1.8 2
5-hydroxytryptamine receptor 2C
CHEMBL225
 Ki 7.22 7.22 60.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
 Ki 5.77 5.77 1700.0 1
5-hydroxytryptamine receptor 1A
CHEMBL214
 Kd 5.6 5.6 2511.9 1
Plasmodium falciparum
CHEMBL364
 IC50 5.36 5.07 4350.0 8
5-hydroxytryptamine receptor 1B
CHEMBL3459
 Ki 5.18 5.18 6600.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 4.52 4.52 29990.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serotonin 2 (5-HT2) receptor Ki = 0.3 nM 9.52 Evaluated for the binding affinity to rat cortical membranes at 5-hydroxytryptam... 3543362
Rattus norvegicus Ki = 0.47 nM 9.33 Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti... 3746815
Serotonin 2 (5-HT2) receptor Ki = 1.0 nM 9.0 Binding affinity to 5-hydroxytryptamine 2 receptor in rat frontal cortical membr... 3543362
Rattus norvegicus IC50 = 1.82 nM 8.74 Compound was evaluated for its activity at membrane-bound receptor (M+L+P fracti... 3746815
Rattus norvegicus Ki = 3.54 nM 8.45 Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solu... 3746815
Rattus norvegicus IC50 = 7.079 nM 8.15 Compound was evaluated for its activity at solubilized receptor (CHAPS/salt-solu... 3746815
5-hydroxytryptamine receptor 2C Ki = 60.0 nM 7.22 Evaluated for the binding affinity to porcine choroid plexus at 5-hydroxytryptam... 3543362
5-hydroxytryptamine receptor 1A Ki = 1700.0 nM 5.77 Evaluated for the binding affinity to hippocampus striatal membranes at 5-hydrox... 3543362
5-hydroxytryptamine receptor 1A Kd = 2511.89 nM 5.6 Binding affinity to 5HT1A receptor 19754201
Plasmodium falciparum IC50 = 4350.0 nM 5.36 DNDI: Malaria in Vitro, 72 hour -
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
5-hydroxytryptamine receptor 1B Ki = 6600.0 nM 5.18 Binding affinity (Ki) to rat cortical membranes at 5-HT1B binding site by using ... 3543362
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910
Trypanosoma brucei rhodesiense IC50 = 29990.0 nM 4.52 DNDI: HAT in Vitro, 72 hour -

Literature References

PubMed DOI Target Context # Activities
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
3746815 10.1021/jm00159a017 Rattus norvegicus 4
3543362 10.1021/jm00384a001 Serotonin 2 (5-HT2) receptor 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL3392926 Leishmania donovani 2
- 10.6019/CHEMBL3392926 NON-PROTEIN TARGET 2
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
- 10.1101/2020.04.03.023846 SARS-CoV-2 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
- 10.6019/CHEMBL3392926 Trypanosoma cruzi 1
- 10.6019/CHEMBL3392926 Plasmodium falciparum 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
3543362 10.1021/jm00384a001 Serotonin 1 (5-HT1) receptor 1
17417631 10.1038/nchembio873 Unchecked 1
19754201 10.1021/jm901096y 5-hydroxytryptamine receptor 1A 1
18262683 10.1016/j.ejmech.2007.12.025 Cavia porcellus 1
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 2C 1
3543362 10.1021/jm00384a001 5-hydroxytryptamine receptor 1B 1

Data from ChEMBL 36 via Core Engine