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Compound Detail

CHEMBL588619

CINCHONINE
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C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL588619
Name CINCHONINE
Phase Preclinical
Structure Type MOL
InChI Key KMPWYEUPVWOPIM-QAMTZSDWSA-N

Known Names

(8r,9s)-cinchonine (9s)-cinchonan-9-ol Cinchonan-9-ol, (9s)- D-cinchonine NSC-6176
3
Targets
17
Activities
3
Assay Types
0
PK Parameters
20
Publications
5
Known Names

Molecular Properties

294.4
MW (Da)
3.16
ALogP
3
HBA
1
HBD
36.4
PSA (Ų)
0.88
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula C19H22N2O
MW 294.40
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness 0.88

Activity Summary

IC50 14 meas. best 8.3
EC50 2 meas. best 7.02
Ki 1 meas. best 4.68

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.3 7.0111 5.0 9
Plasmodium falciparum
CHEMBL364
 EC50 7.02 6.99 95.3 2
Cytochrome P450 2D6
CHEMBL289
 IC50 5.75 5.75 1800.0 1
Cytochrome P450 2D6
CHEMBL289
 Ki 4.68 4.68 21000.0 1
Heme
CHEMBL4651321
 IC50 4.64 4.64 23000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antiplasmodial activity against Plasmodium falciparum 3D7 infected in RBCs by fi... 20547797
Plasmodium falciparum IC50 = 21.0 nM 7.68 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... -
Plasmodium falciparum IC50 = 22.0 nM 7.66 Antimalarial activity against chloroquine sensitive Plasmodium falciparum HB3 af... 22512909
Plasmodium falciparum IC50 = 51.0 nM 7.29 In vitro inhibition of parasite development of Plasmodium falciparum W2 in human... 11992775
Plasmodium falciparum IC50 = 56.0 nM 7.25 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 ass... -
Plasmodium falciparum IC50 = 82.0 nM 7.09 Antimalarial activity against chloroquine resistant Plasmodium falciparum Dd2 af... 22512909
Plasmodium falciparum EC50 = 95.3 nM 7.02 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Plasmodium falciparum EC50 = 110.0 nM 6.96 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum IC50 = 220.0 nM 6.66 In vitro antimalarial activity against Plasmodium falciparum W2 in human erythro... 11992775
Plasmodium falciparum IC50 = 292.5 nM 6.53 Antiplasmodial activity against Plasmodium falciparum 3D7 assessed as reduction ... 26063305
Cytochrome P450 2D6 IC50 = 1800.0 nM 5.75 Inhibitory concentration against cytochrome P450 2D6 15481972
Cytochrome P450 2D6 Ki = 21000.0 nM 4.68 Binding affinity for cytochrome P450 2D6 15481972
Plasmodium falciparum IC50 = 23000.0 nM 4.64 Antimicrobial activity against Plasmodium falciparum 20185316
Heme IC50 = 23000.0 nM 4.64 Inhibition of heme polymerization in Plasmodium falciparum after 15 min by liqui... -

Literature References

PubMed DOI Target Context # Activities
20485427 10.1038/nature09107 Plasmodium falciparum 4
23816880 10.1016/j.ejmech.2013.06.004 Unchecked 3
- 10.1007/s00044-007-9025-8 Plasmodium falciparum 2
15481972 10.1021/jm049934e Cytochrome P450 2D6 2
26063305 10.1016/j.ejmech.2015.05.044 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
11992775 10.1016/s0960-894x(02)00173-7 Plasmodium falciparum 2
22846917 10.1016/j.bmcl.2012.06.062 Trichomonas vaginalis 2
22512909 10.1016/j.bmc.2012.03.042 Unchecked 2
22512909 10.1016/j.bmc.2012.03.042 Plasmodium falciparum 2
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1
22846917 10.1016/j.bmcl.2012.06.062 ADMET 1
22846917 10.1016/j.bmcl.2012.06.062 Spermatozoa 1
20547797 10.1128/aac.00431-10 Plasmodium falciparum 1
18579783 10.1073/pnas.0802982105 Huh-7 1
18579783 10.1073/pnas.0802982105 Unchecked 1
20485427 10.1038/nature09107 Unchecked 1
1710653 10.1021/np50073a012 Human immunodeficiency virus type 1 reverse transcriptase 1

Data from ChEMBL 36 via Core Engine