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Compound Detail

CHEMBL4454693

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CCc1nc(N)nc(N)c1OCCCOc1ccc(-c2c(N)nc(N)nc2CC)cc1.Cl.Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4454693
Phase Preclinical
Structure Type MOL
InChI Key WYOSQZWZDHJADR-UHFFFAOYSA-N
Parent Compound CHEMBL4462726
Active Moiety CHEMBL4462726
3
Targets
11
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

424.5
MW (Da)
2.24
ALogP
10
HBA
4
HBD
174.1
PSA (Ų)
0.37
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H30Cl2N8O2
MW 497.43
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -0.40

Activity Summary

Ki 6 meas. best 9.51
IC50 5 meas. best 7.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.51 8.816 0.3 5
Dihydrofolate reductase
CHEMBL202
 Ki 7.7 7.7 20.2 1
Plasmodium falciparum
CHEMBL364
 IC50 7.2 5.866 63.0 5

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.31 nM 9.51 Inhibition of Plasmodium falciparum TM4/8.2 wild type DHFR NCSI haplotype assess... 30613332
Unchecked Ki = 0.74 nM 9.13 Inhibition of Plasmodium falciparum W2 DHFR IRNI haplotype N51I/C59R/S108N tripl... 30613332
Unchecked Ki = 1.1 nM 8.96 Inhibition of Plasmodium falciparum K1CB1 DHFR NRNI haplotype C59R/S108N double ... 30613332
Unchecked Ki = 5.72 nM 8.24 Inhibition of Plasmodium falciparum CSL-2 DHFR NRNL haplotype C59R/S108N/I164L t... 30613332
Unchecked Ki = 5.8 nM 8.24 Inhibition of Plasmodium falciparum V1/S DHFR IRNL haplotype N51I/C59R/S108N/I16... 30613332
Dihydrofolate reductase Ki = 20.2 nM 7.7 Inhibition of human DHFR assessed as reduction in NADPH consumption by spectroph... 30613332
Plasmodium falciparum IC50 = 63.0 nM 7.2 Antiplasmodial activity against Plasmodium falciparum TM4/8.2 harboring wild typ... 30613332
Plasmodium falciparum IC50 = 1840.0 nM 5.74 Antiplasmodial activity against Plasmodium falciparum K1CB1 harboring DHFR NRNI ... 30613332
Plasmodium falciparum IC50 = 2350.0 nM 5.63 Antiplasmodial activity against Plasmodium falciparum W2 harboring DHFR IRNI hap... 30613332
Plasmodium falciparum IC50 = 3950.0 nM 5.4 Antiplasmodial activity against Plasmodium falciparum CSL-2 harboring DHFR NRNL ... 30613332
Plasmodium falciparum IC50 = 4400.0 nM 5.36 Antiplasmodial activity against Plasmodium falciparum V1/S harboring DHFR IRNL h... 30613332

Literature References

PubMed DOI Target Context # Activities
30613332 10.1021/acsmedchemlett.8b00389 Unchecked 7
30613332 10.1021/acsmedchemlett.8b00389 Plasmodium falciparum 5
30613332 10.1021/acsmedchemlett.8b00389 Dihydrofolate reductase 1
30613332 10.1021/acsmedchemlett.8b00389 Vero 1

Data from ChEMBL 36 via Core Engine