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Compound Detail

CHEMBL147587

ISOQUINE
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CCN(CC)Cc1ccc(Nc2ccnc3cc(Cl)ccc23)cc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL147587
Name ISOQUINE
Phase Preclinical
Structure Type MOL
InChI Key QGFYFOHMBDMGBZ-UHFFFAOYSA-N
7
Targets
25
Activities
1
Assay Types
16
PK Parameters
20
Publications
0
Known Names

Molecular Properties

355.9
MW (Da)
5.18
ALogP
4
HBA
2
HBD
48.4
PSA (Ų)
0.64
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C20H22ClN3O
MW 355.87
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.23

Activity Summary

IC50 25 meas. best 8.37

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.37 7.8979 4.3 14
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.41 5.41 3900.0 1
Cytochrome P450 2D6
CHEMBL289
 IC50 5.16 5.16 7000.0 2
Cytochrome P450 2C8
CHEMBL3721
 IC50 4.89 4.89 13000.0 2
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.64 4.64 23000.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.41 4.41 39000.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.12 4.12 75000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 219.0 mL.min-1.kg-1 Mus musculus
CL 89.2 mL.min-1.kg-1 Rattus norvegicus
CL 41.0 mL.min-1.g-1 Mus musculus
CL 11.0 mL.min-1.g-1 Rattus norvegicus
CL 23.0 mL.min-1.g-1 Canis lupus familiaris
CL 21.0 mL.min-1.g-1 Macaca mulatta
CL 3.3 mL.min-1.g-1 Homo sapiens
CL 219.0 mL.min-1.kg-1 Mus musculus
CL 89.0 mL.min-1.kg-1 Rattus norvegicus
CL 151.0 mL.min-1.kg-1 Canis lupus familiaris
CL - - Macaca mulatta
F 21.0 % Mus musculus
F 17.0 % Rattus norvegicus
F 21.0 % Mus musculus
F 17.0 % Rattus norvegicus
F - % Macaca mulatta

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 4.3 nM 8.37 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Thai a... 17485145
Plasmodium falciparum IC50 = 5.4 nM 8.27 Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1R ... 17485145
Plasmodium falciparum IC50 = 6.01 nM 8.22 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 20466465
Plasmodium falciparum IC50 = 7.3 nM 8.14 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 aft... 17485145
Plasmodium falciparum IC50 = 7.8 nM 8.11 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 19284751
Plasmodium falciparum IC50 = 11.6 nM 7.94 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 19222165
Plasmodium falciparum IC50 = 12.65 nM 7.9 In vitro antimalarial activity against Plasmodium falciparum HB 14584944
Plasmodium falciparum IC50 = 12.6 nM 7.9 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum HB3 in... 19222165
Plasmodium falciparum IC50 = 17.63 nM 7.75 In vitro antimalarial activity against chloroquine-resistant Plasmodium falcipar... 14584944
Plasmodium falciparum IC50 = 17.6 nM 7.75 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 in ... 19222165
Plasmodium falciparum IC50 = 23.7 nM 7.62 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D10 as... 18562202
Plasmodium falciparum IC50 = 27.0 nM 7.57 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D10 ... 23145816
Plasmodium falciparum IC50 = 30.2 nM 7.52 Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 as ... 18562202
Plasmodium falciparum IC50 = 31.0 nM 7.51 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 i... 23145816
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 3900.0 nM 5.41 Inhibition of human cloned ERG 19222165
Cytochrome P450 2D6 IC50 = 7000.0 nM 5.16 Inhibition of human CYP2D6 19284751
Cytochrome P450 2D6 IC50 = 7000.0 nM 5.16 Inhibition of human recombinant CYP2D6 19222165
Cytochrome P450 2C8 IC50 = 13000.0 nM 4.89 Inhibition of human CYP2C8 19284751
Cytochrome P450 2C8 IC50 = 13000.0 nM 4.89 Inhibition of human recombinant CYP2C8 19222165
Cytochrome P450 1A2 IC50 = 23000.0 nM 4.64 Inhibition of human CYP1A2 19284751

Literature References

PubMed DOI Target Context # Activities
18562202 10.1016/j.bmc.2008.05.068 Plasmodium falciparum 4
19284751 10.1021/jm8012757 Plasmodium yoelii 4
23145816 10.1021/jm300831b Plasmodium falciparum 3
19222165 10.1021/jm8012618 Plasmodium falciparum 3
19222165 10.1021/jm8012618 Rhesus monkey 3
19284751 10.1021/jm8012757 ADMET 3
17485145 10.1016/j.ejmech.2007.03.008 Plasmodium falciparum 3
19284751 10.1021/jm8012757 Plasmodium berghei 2
19284751 10.1021/jm8012757 Mus musculus 2
19284751 10.1021/jm8012757 Rattus norvegicus 2
19284751 10.1021/jm8012757 Liver microsomes 2
19284751 10.1021/jm8012757 Cytochrome P450 3A4 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18562202 10.1016/j.bmc.2008.05.068 ADMET 2
19222165 10.1021/jm8012618 Cytochrome P450 3A4 2
19222165 10.1021/jm8012618 Rattus norvegicus 2
14584944 10.1021/jm030796n Plasmodium falciparum 2
19222165 10.1021/jm8012618 Plasmodium berghei 2
19222165 10.1021/jm8012618 Mus musculus 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1

Data from ChEMBL 36 via Core Engine