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Compound Detail

CHEMBL4745404

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N[C@H](C(=O)N1CC(CNc2ccc(F)cc2)C2(C1)CN(c1cc(F)cc(F)c1)C2)c1ccc(O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4745404
Phase Preclinical
Structure Type MOL
InChI Key KRGNGQPCSCNVFC-LYIYLXCWSA-N
2
Targets
21
Activities
1
Assay Types
9
PK Parameters
4
Publications
0
Known Names

Molecular Properties

496.5
MW (Da)
3.89
ALogP
5
HBA
3
HBD
81.8
PSA (Ų)
0.48
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H27F3N4O2
MW 496.53
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness -0.44

Activity Summary

IC50 21 meas. best 8.05

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 8.05 6.3917 8.9 18
Plasmodium falciparum
CHEMBL364
 IC50 7.57 7.0067 27.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 1489.59 ng.hr.mL-1 Mus musculus
CL 33.7 mL.min-1.kg-1 Mus musculus
CL 2155.0 mL.min-1.kg-1 Mus musculus
F 1.0 % Mus musculus
T1/2 2.5 hr Homo sapiens
T1/2 2.5 hr Rattus norvegicus
T1/2 2.5 hr Mus musculus
T1/2 8.0 hr Mus musculus
Vd 23.5 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 8.9 nM 8.05 Binding affinity to CARL E1104K mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 26.3 nM 7.58 Binding affinity to wild type CARL in multidrug-resistant Plasmodium falciparum ... 33573376
Plasmodium falciparum IC50 = 27.0 nM 7.57 Antiplasmodial activity against asexual stage (V) Plasmodium falciparum NF54 gam... 33573376
Unchecked IC50 = 39.5 nM 7.4 Binding affinity to CARL 11072V mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 63.7 nM 7.2 Binding affinity to CARL A1122E mutant in multidrug-resistant Plasmodium falcipa... 33573376
Plasmodium falciparum IC50 = 75.0 nM 7.12 Antiplasmodial activity against multidrug-sensitive Plasmodium falciparum NF54 t... 33573376
Unchecked IC50 = 90.5 nM 7.04 Binding affinity to CARL V1053G mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 98.0 nM 7.01 Binding affinity to CARL L1073Q mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 151.9 nM 6.82 Binding affinity to wild type CARL in multidrug-resistant Plasmodium falciparum ... 33573376
Unchecked IC50 = 351.3 nM 6.45 Binding affinity to CARL 11072V mutant in multidrug-resistant Plasmodium falcipa... 33573376
Plasmodium falciparum IC50 = 471.0 nM 6.33 Antiplasmodial activity against asexual stage (V) Plasmodium falciparum NF54 gam... 33573376
Unchecked IC50 = 914.4 nM 6.04 Binding affinity to CARL V1053G mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 967.1 nM 6.01 Binding affinity to CARL E1104K mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 1101.8 nM 5.96 Binding affinity to CARL I1139K mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 1373.5 nM 5.86 Binding affinity to CARL M1050I mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 1450.3 nM 5.84 Binding affinity to CARL L1108W mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 1692.7 nM 5.77 Binding affinity to CARL M1050I mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 1820.6 nM 5.74 Binding affinity to CARL L1108W mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 2610.8 nM 5.58 Binding affinity to CARL A1122E mutant in multidrug-resistant Plasmodium falcipa... 33573376
Unchecked IC50 = 3935.0 nM 5.41 Binding affinity to CARL L1073Q mutant in multidrug-resistant Plasmodium falcipa... 33573376

Literature References

PubMed DOI Target Context # Activities
33573376 10.1021/acs.jmedchem.1c00034 Unchecked 35
33573376 10.1021/acs.jmedchem.1c00034 Plasmodium falciparum 19
33573376 10.1021/acs.jmedchem.1c00034 ADMET 15
33573376 10.1021/acs.jmedchem.1c00034 No relevant target 1

Data from ChEMBL 36 via Core Engine