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Compound Detail

CHEMBL1630

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CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1630
Phase Preclinical
Structure Type MOL
InChI Key KBTNVJNLEFHBSO-UHFFFAOYSA-N
Parent Compound CHEMBL682
Active Moiety CHEMBL682

Known Names

TCMDC-123932
19
Targets
144
Activities
4
Assay Types
30
PK Parameters
20
Publications
1
Known Names

Molecular Properties

355.9
MW (Da)
5.18
ALogP
4
HBA
2
HBD
48.4
PSA (Ų)
0.60
QED
1
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H23Cl2N3O
MW 392.33
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.16

Activity Summary

IC50 139 meas. best 9.0
EC50 3 meas. best 7.99
Kd 1 meas. best 4.28
Ki 1 meas. best 7.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 9.0 7.9199 1.0 86
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.37 8.37 4.3 1
Plasmodium vivax
CHEMBL613013
 IC50 8.11 7.8227 7.8 15
Plasmodium falciparum
CHEMBL364
 EC50 7.99 7.9433 10.3 3
Plasmodium malariae
CHEMBL613257
 IC50 7.72 7.69 19.1 2
Histamine N-methyltransferase
CHEMBL2190
 Ki 7.72 7.72 19.0 1
Unchecked
CHEMBL612545
 IC50 6.07 4.698 850.0 10
Leishmania amazonensis
CHEMBL612877
 IC50 6.02 6.02 950.0 1
Leishmania donovani
CHEMBL367
 IC50 5.85 5.85 1400.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.62 5.62 2400.0 1
Cytochrome P450 2C8
CHEMBL3721
 IC50 5.57 5.57 2700.0 2
Cytochrome P450 2D6
CHEMBL289
 IC50 5.21 5.21 6100.0 2
No relevant target
CHEMBL2362975
 IC50 5.17 5.17 6800.0 1
Heme
CHEMBL4651321
 IC50 4.82 4.495 15000.0 2
Cytochrome P450 1A2
CHEMBL3356
 IC50 4.82 4.82 15000.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.55 4.55 28000.0 2
Heparanase
CHEMBL3921
 Kd 4.28 4.28 52600.0 1
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.21 4.21 62000.0 2
Cytochrome P450 2C19
CHEMBL3622
 IC50 4.07 4.07 85000.0 1
KB
CHEMBL398
 IC50 4.05 4.05 90000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 28.9 ng.hr.mL-1 Homo sapiens
AUC 39.3 ng.hr.mL-1 Homo sapiens
AUC 11242.0 ng.hr.mL-1 Homo sapiens
AUC 14770.0 ng.hr.mL-1 Homo sapiens
AUC 154.0 ng.hr.mL-1 Homo sapiens
AUC 8437.0 ng.hr.mL-1 Homo sapiens
AUC 149.0 ng/ml Homo sapiens
AUC 62.0 ng/ml Homo sapiens
AUC 38516.0 ng.hr.mL-1 Homo sapiens
CL 50.0 mL.min-1.g-1 Mus musculus
CL 9.9 mL.min-1.g-1 Rattus norvegicus
CL 12.0 mL.min-1.g-1 Canis lupus familiaris
CL 29.0 mL.min-1.g-1 Macaca mulatta
CL 9.8 mL.min-1.g-1 Homo sapiens
Cmax 14.61 nM Homo sapiens
Cmax 660.35 nM Homo sapiens
Cmax 3329.87 nM Homo sapiens
Ka 1.1 10^5/M Homo sapiens
Ka 2.0 10^4/M Homo sapiens
Ka 0.62 10^4M Homo sapiens
Ka 13.8 10'-4/M Homo sapiens
Ka 8.39 10'-4/M Homo sapiens
Ka 4.59 10'-4/M Homo sapiens
Ka 7.31 10'-4/M Homo sapiens
Ka 11.36 10'-4/M Homo sapiens
T1/2 3.3 hr Homo sapiens
T1/2 60.0 hr Homo sapiens
T1/2 2.0 hr Homo sapiens
T1/2 104.0 hr Homo sapiens
Tmax 47.9 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 1.0 nM 9.0 Antiplasmodial activity chloroquine-sensitive Plasmodium falciparum 3D7 infected... 23896611
Plasmodium falciparum IC50 = 2.0 nM 8.7 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 as... 21135175
Plasmodium falciparum IC50 = 2.15 nM 8.67 Antimalarial activity against chloroquine-susceptible Plasmodium falciparum 3D7 ... 19811859
Plasmodium falciparum IC50 = 2.47 nM 8.61 In vitro inhibitory activity against chloroquine-sensitive Plasmodium falciparum... 10425085
Plasmodium falciparum IC50 = 3.7 nM 8.43 In vitro inhibition of chloroquine-sensitive Plasmodium falciparum HB3 9046333
NON-PROTEIN TARGET IC50 = 4.3 nM 8.37 Antimalarial activity against Plasmodium ovale ring stage infected in red blood ... 20937779
Plasmodium falciparum IC50 = 4.5 nM 8.35 Antimalarial activity against Plasmodium falciparum GC03 18341274
Plasmodium falciparum IC50 = 4.6 nM 8.34 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Thai a... 17485145
Plasmodium falciparum IC50 = 4.6 nM 8.34 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum THAI/T... 18226428
Plasmodium falciparum IC50 = 4.7 nM 8.33 Antimalarial activity against Plasmodium falciparum PH3 18341274
Plasmodium falciparum IC50 = 4.8 nM 8.32 Antimalarial activity after 24 hrs against chloroquine-resistant Plasmodium falc... 18226428
Plasmodium falciparum IC50 = 4.8 nM 8.32 Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1R ... 17485145
Plasmodium falciparum IC50 = 4.9 nM 8.31 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum 3D7 in... 22182577
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antimalarial activity against Plasmodium falciparum assessed as parasites growth... 21135175
Plasmodium falciparum IC50 = 5.0 nM 8.3 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum W2 i... 22749280
Plasmodium falciparum IC50 = 5.5 nM 8.26 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum HB3 19284751
Plasmodium falciparum IC50 = 5.7 nM 8.24 Antimalarial activity against ring stage of Plasmodium falciparum assessed as pa... 21135175
Plasmodium falciparum IC50 = 5.7 nM 8.24 Antimalarial activity against Plasmodium falciparum infected in human erythrocyt... 20876370
Plasmodium falciparum IC50 = 5.9 nM 8.23 Antimalarial activity against Plasmodium falciparum HB3 18341274
Plasmodium falciparum IC50 = 6.1 nM 8.21 Antimalarial activity against Plasmodium falciparum DD2 18341274

Literature References

PubMed DOI Target Context # Activities
20065053 10.1128/aac.01161-09 Homo sapiens 22
22658498 10.1016/j.ejmech.2012.05.007 Albumin 12
17404003 10.1128/aac.01479-06 Plasmodium falciparum 12
19841149 10.1128/aac.00679-09 Homo sapiens 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23586757 10.1021/jm400282d Unchecked 10
20485428 10.1038/nature09099 Plasmodium falciparum 9
19284751 10.1021/jm8012757 Plasmodium falciparum 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
11495593 10.1021/jm010842o MRC5 7
22182577 10.1016/j.bmc.2011.11.053 Plasmodium falciparum 7
18180357 10.1128/aac.01334-07 Plasmodium vivax 7
18341274 10.1021/jm701435h Plasmodium falciparum 7
11495593 10.1021/jm010842o ADMET 5
21135175 10.1128/aac.01220-10 Plasmodium falciparum 5
18316523 10.1128/aac.01478-07 Plasmodium falciparum 5
3712383 10.1021/jm00156a009 Plasmodium berghei 5
18779360 10.1128/aac.00673-07 Homo sapiens 5
19284751 10.1021/jm8012757 Mus musculus 5
19284751 10.1021/jm8012757 ADMET 5

Data from ChEMBL 36 via Core Engine