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Compound Detail

CHEMBL3819601

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Cc1nc(N)nc(N)c1OCCCOc1cc(Cl)c(Cl)cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3819601
Phase Preclinical
Structure Type MOL
InChI Key KNUBCZHIBGZRJT-UHFFFAOYSA-N
4
Targets
12
Activities
2
Assay Types
2
PK Parameters
7
Publications
0
Known Names

Molecular Properties

377.7
MW (Da)
3.76
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.59
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H15Cl3N4O2
MW 377.66
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.79

Activity Summary

IC50 6 meas. best 6.64
Ki 6 meas. best 9.31

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.31 8.604 0.5 5
Dihydrofolate reductase
CHEMBL202
 Ki 7.32 7.32 47.6 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 6.64 6.64 229.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.64 5.764 230.0 5

Pharmacokinetic Data

Parameter Value Units Species
F 83.0 % Rattus norvegicus
F 83.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.49 nM 9.31 Inhibition of Plasmodium falciparum TM4/8.2 wild type DHFR NCSI haplotype assess... 30613332
Unchecked Ki = 2.61 nM 8.58 Inhibition of Plasmodium falciparum W2 DHFR IRNI haplotype N51I/C59R/S108N tripl... 30613332
Unchecked Ki = 3.15 nM 8.5 Inhibition of Plasmodium falciparum K1CB1 DHFR NRNI haplotype C59R/S108N double ... 30613332
Unchecked Ki = 4.21 nM 8.38 Inhibition of Plasmodium falciparum CSL-2 DHFR NRNL haplotype C59R/S108N/I164L t... 30613332
Unchecked Ki = 5.59 nM 8.25 Inhibition of Plasmodium falciparum V1/S DHFR IRNL haplotype N51I/C59R/S108N/I16... 30613332
Dihydrofolate reductase Ki = 47.6 nM 7.32 Inhibition of human DHFR assessed as reduction in NADPH consumption by spectroph... 30613332
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 229.0 nM 6.64 Inhibition of Plasmodium falciparum DHFR 29111368
Plasmodium falciparum IC50 = 230.0 nM 6.64 Antiplasmodial activity against Plasmodium falciparum TM4/8.2 harboring wild typ... 30613332
Plasmodium falciparum IC50 = 1920.0 nM 5.72 Antiplasmodial activity against Plasmodium falciparum K1CB1 harboring DHFR NRNI ... 30613332
Plasmodium falciparum IC50 = 2270.0 nM 5.64 Antiplasmodial activity against Plasmodium falciparum W2 harboring DHFR IRNI hap... 30613332
Plasmodium falciparum IC50 = 3500.0 nM 5.46 Antiplasmodial activity against Plasmodium falciparum V1/S harboring DHFR IRNL h... 30613332
Plasmodium falciparum IC50 = 4400.0 nM 5.36 Antiplasmodial activity against Plasmodium falciparum CSL-2 harboring DHFR NRNL ... 30613332

Literature References

PubMed DOI Target Context # Activities
30613332 10.1021/acsmedchemlett.8b00389 Unchecked 7
30613332 10.1021/acsmedchemlett.8b00389 Plasmodium falciparum 5
- 10.1039/C6MD00084C Rattus norvegicus 1
29111368 10.1016/j.bmc.2017.10.017 Bifunctional dihydrofolate reductase-thymidylate synthase 1
30108934 10.1039/C7MD00637C Rattus norvegicus 1
30613332 10.1021/acsmedchemlett.8b00389 Dihydrofolate reductase 1
30613332 10.1021/acsmedchemlett.8b00389 Vero 1

Data from ChEMBL 36 via Core Engine