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Compound Detail

CHEMBL35228

PYRONARIDINE
🧪 Phase III
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🧪 Phase III
COc1ccc2nc3cc(Cl)ccc3c(Nc3cc(CN4CCCC4)c(O)c(CN4CCCC4)c3)c2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL35228
Name PYRONARIDINE
Phase Phase III
Structure Type MOL
InChI Key DJUFPMUQJKWIJB-UHFFFAOYSA-N

Known Names

Malaridine Pironaridina Pyronaridine
16
Targets
70
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
6
Indications

Molecular Properties

518.1
MW (Da)
6.09
ALogP
7
HBA
2
HBD
73.8
PSA (Ų)
0.23
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product

Extended Properties

Molecular Formula C29H32ClN5O2
MW 518.06
Aromatic Rings 4
Heavy Atoms 37
NP-Likeness -0.83

Indications

Malaria Malaria, Falciparum Severe Acute Respiratory Syndrome Conjunctivitis, Allergic Infections Schistosomiasis haematobia

Activity Summary

IC50 62 meas. best 9.14
EC50 7 meas. best 7.8
Kd 1 meas. best 5.13

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.14 9.14 0.7 1
Plasmodium falciparum
CHEMBL364
 IC50 9.1 7.7271 0.8 38
HEK293
CHEMBL614818
 IC50 8.75 6.0071 1.8 7
Plasmodium vivax
CHEMBL613013
 IC50 8.62 8.535 2.4 4
Plasmodium malariae
CHEMBL613257
 IC50 8.39 8.25 4.1 2
Plasmodium falciparum
CHEMBL364
 EC50 7.8 6.7114 16.0 7
Ebolavirus
CHEMBL4434621
 IC50 6.09 6.09 820.0 1
Vero 76
CHEMBL4296509
 IC50 5.89 5.89 1300.0 1
SH-SY5Y
CHEMBL614910
 IC50 5.77 5.77 1700.0 1
Hemozoin
CHEMBL613898
 IC50 5.66 5.66 2200.0 1
HeLa
CHEMBL399
 IC50 5.51 5.51 3100.0 1
SK-N-AS
CHEMBL1075578
 IC50 5.46 5.46 3450.0 1
Jurkat
CHEMBL397
 IC50 5.4 5.4 4000.0 1
HT-1080
CHEMBL614580
 IC50 5.37 5.37 4230.0 1
DNA topoisomerase 2
CHEMBL1741266
 IC50 5.26 5.26 5500.0 1
Unchecked
CHEMBL612545
 Kd 5.13 5.13 7340.0 1
Heme
CHEMBL4651321
 IC50 4.19 4.19 64000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.72 nM 9.14 Antimalarial activity against Plasmodium ovale ring stage infected in red blood ... 20937779
Plasmodium falciparum IC50 = 0.8 nM 9.1 Inhibitory concentration against Plasmodium falciparum W2 infected erythrocytes 8182707
Plasmodium falciparum IC50 = 1.0 nM 9.0 Inhibitory concentration against Plasmodium falciparum D6 infected erythrocytes 8182707
Plasmodium falciparum IC50 = 1.6 nM 8.8 Antimalarial activity against Plasmodium falciparum at the ring stage infected i... 20876370
HEK293 IC50 = 1.79 nM 8.75 Cytotoxicity against HEK293 cells assessed as cell viability after 72 hrs by res... 26651537
Plasmodium falciparum IC50 = 1.92 nM 8.72 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 20876370
Plasmodium vivax IC50 = 2.4 nM 8.62 Antimalarial activity against Plasmodium vivax with >50% parasites at ring stage... 20876370
Plasmodium vivax IC50 = 2.5 nM 8.6 Antimalarial activity against Plasmodium vivax at the ring stage infected in hum... 20876370
Plasmodium vivax IC50 = 2.58 nM 8.59 Antimalarial activity against Plasmodium vivax infected in human erythrocytes as... 20876370
Plasmodium falciparum IC50 = 2.7 nM 8.57 Inhibitory concentration IC50 against Plasmodium falciparum K1 by [3H]hypoxanthi... 8182707
Plasmodium falciparum IC50 = 3.2 nM 8.49 OSM: Inhibition of Plasmodium falciparum 3D7 growth. IC50 values determined from... -
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum 3D7 ... 26651537
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 28001067
Plasmodium falciparum IC50 = 3.6 nM 8.44 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 32067457
Plasmodium malariae IC50 = 4.1 nM 8.39 Antimalarial activity against Plasmodium malariae ring stage infected in red blo... 20937779
Plasmodium vivax IC50 = 4.7 nM 8.33 Antimalarial activity against Plasmodium vivax trophozoites infected in human er... 20876370
Plasmodium falciparum IC50 = 5.7 nM 8.24 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... -
Plasmodium falciparum IC50 = 6.0 nM 8.22 Antimalarial activity against Plasmodium falciparum KT1 gametocytes 23075290
Plasmodium falciparum IC50 = 7.0 nM 8.15 Antimalarial activity against Plasmodium falciparum 3D7 after 72 hrs by DAPI sta... 30537832
Plasmodium falciparum IC50 = 7.4 nM 8.13 Antimalarial activity against synchronous ring stage of Plasmodium falciparum 3D... 34058708

Literature References

PubMed DOI Target Context # Activities
8182707 10.1021/jm00036a014 Plasmodium falciparum 4
20876370 10.1128/aac.00801-10 Plasmodium vivax 4
30537832 10.1021/acs.jmedchem.8b01310 HEK293 3
20876370 10.1128/aac.00801-10 Plasmodium falciparum 3
28080063 10.1021/acs.jmedchem.6b01673 Plasmodium falciparum 3
15194484 10.1016/j.bbrc.2004.05.099 ATP-dependent translocase ABCB1 3
23075290 10.1021/jm3005898 Plasmodium falciparum 3
36208544 10.1016/j.bmc.2022.117043 SH-SY5Y 3
23927763 10.1021/jm4004279 Plasmodium falciparum 3
28001067 10.1021/acs.jnatprod.6b00759 Plasmodium falciparum 2
8182707 10.1021/jm00036a014 Jurkat 2
26651537 10.1021/acs.jnatprod.5b00581 Plasmodium falciparum 2
28400231 10.1016/j.bmcl.2017.03.065 Plasmodium falciparum 2
29969262 10.1021/acs.jnatprod.8b00154 Plasmodium falciparum 2
30245402 10.1016/j.ejmech.2018.09.018 Plasmodium falciparum 2
30865443 10.1021/acs.jnatprod.8b00956 Plasmodium falciparum 2
- 10.1007/s00044-007-9025-8 Plasmodium falciparum 2
- 10.6019/CHEMBL2113921 Plasmodium falciparum 2
30537832 10.1021/acs.jmedchem.8b01310 Plasmodium falciparum 2
20937779 10.1128/aac.01122-10 Plasmodium malariae 2

Data from ChEMBL 36 via Core Engine