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Compound Detail

CHEMBL1235

DESETHYL AMODIAQUINE
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CCNCc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O

Basic Information

ChEMBL ID CHEMBL1235
Name DESETHYL AMODIAQUINE
Phase Preclinical
Structure Type MOL
InChI Key VRXFDHAGFYWGHT-UHFFFAOYSA-N

Known Names

N-Monodesethylamodiaquine (Deaq)
9
Targets
91
Activities
1
Assay Types
5
PK Parameters
20
Publications
1
Known Names

Molecular Properties

327.8
MW (Da)
4.45
ALogP
4
HBA
3
HBD
57.2
PSA (Ų)
0.61
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H18ClN3O
MW 327.82
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -0.83

Activity Summary

IC50 91 meas. best 8.35

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
IC50 8.35 7.3337 4.5 76
Cytochrome P450 2D6
CHEMBL289
IC50 5.19 5.19 6400.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.02 5.02 9500.0 1
Cytochrome P450 2C8
CHEMBL3721
IC50 4.7 4.7 20000.0 2
Cytochrome P450 3A4
CHEMBL340
IC50 4.62 4.4133 24000.0 3
Cytochrome P450 1A2
CHEMBL3356
IC50 4.55 4.55 28000.0 2
Heme
CHEMBL4651321
IC50 4.37 4.37 43000.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 4.27 4.27 54000.0 2
Cytochrome P450 2C9
CHEMBL3397
IC50 4.24 4.24 58000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.g-1 Mus musculus
CL 1.9 mL.min-1.g-1 Rattus norvegicus
CL 4.4 mL.min-1.g-1 Canis lupus familiaris
CL 1.6 mL.min-1.g-1 Macaca mulatta
CL 0.5 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 4.5 nM 8.35 In vitro inhibition of chloroquine-sensitive Plasmodium falciparum HB3 9046333
Plasmodium falciparum IC50 = 6.3 nM 8.2 Antimicrobial activity against Plasmodium falciparum harboring mdr1 N86Y/D1246Y/... 20065051
Plasmodium falciparum IC50 = 6.9 nM 8.16 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... -
Plasmodium falciparum IC50 = 8.3 nM 8.08 Antimalarial activity against Plasmodium falciparum assessed as parasite growth ... 19704124
Plasmodium falciparum IC50 = 16.0 nM 7.8 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 37163950
Plasmodium falciparum IC50 = 17.5 nM 7.76 Antiplasmodial activity against chloroquine-susceptible Plasmodium falciparum D6... 20329733
Plasmodium falciparum IC50 = 19.5 nM 7.71 Antiplasmodial activity against chloroquine-susceptible Plasmodium falciparum 3D... 20329733
Plasmodium falciparum IC50 = 20.0 nM 7.7 Antimalarial activity against Plasmodium falciparum IMT 10354 assessed as inhibi... 20547801
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum W2 assessed as incorporation... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT 8425 assessed as incorpo... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT 9881 assessed as incorpo... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT 10336 assessed as incorp... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT 10500 assessed as incorp... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT K14 assessed as incorpor... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT K2 assessed as incorpora... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT K4 assessed as incorpora... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT L1 assessed as incorpora... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT Vol assessed as incorpor... 19307369
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum D6 assessed as inhibition of... 20547801
Plasmodium falciparum IC50 = 23.0 nM 7.64 Antimalarial activity against Plasmodium falciparum IMT 16332 assessed as incorp... 19307369

Literature References

PubMed DOI Target Context # Activities
20329733 10.1021/jm9018383 Plasmodium falciparum 24
20547801 10.1128/aac.00183-10 Plasmodium falciparum 23
19307369 10.1128/aac.01462-08 Plasmodium falciparum 22
20065051 10.1128/aac.01412-09 Plasmodium falciparum 6
18779360 10.1128/aac.00673-07 Homo sapiens 5
19284751 10.1021/jm8012757 ADMET 3
19284751 10.1021/jm8012757 Liver microsomes 2
19284751 10.1021/jm8012757 Cytochrome P450 3A4 2
19704124 10.1128/aac.00610-09 Plasmodium falciparum 2
34782182 10.1016/j.ejmech.2021.113981 Plasmodium falciparum 2
- 10.1007/s00044-007-9025-8 Plasmodium falciparum 2
19222165 10.1021/jm8012618 Cytochrome P450 3A4 2
37163950 10.1016/j.ejmech.2023.115458 Plasmodium falciparum 2
19222165 10.1021/jm8012618 Plasmodium yoelii 1
19222165 10.1021/jm8012618 Cytochrome P450 2C19 1
19222165 10.1021/jm8012618 Homo sapiens 1
19222165 10.1021/jm8012618 Mus musculus 1
19284751 10.1021/jm8012757 Cytochrome P450 2C9 1
19284751 10.1021/jm8012757 Cytochrome P450 2C8 1
19284751 10.1021/jm8012757 Cytochrome P450 1A2 1

Data from ChEMBL 36 via Core Engine