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Compound Detail

CHEMBL22138

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Nc1ncc(Cc2ccc(OCc3ccccc3)c(OCc3ccccc3)c2)c(N)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22138
Phase Preclinical
Structure Type MOL
InChI Key KYJSISOHUNITEJ-UHFFFAOYSA-N
2
Targets
17
Activities
2
Assay Types
0
PK Parameters
4
Publications
0
Known Names

Molecular Properties

412.5
MW (Da)
4.39
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.45
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H24N4O2
MW 412.49
Aromatic Rings 4
Heavy Atoms 31
NP-Likeness -0.28

Activity Summary

IC50 10 meas. best 7.22
Ki 7 meas. best 8.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.77 7.3914 1.7 7
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.22 5.745 60.0 8
Plasmodium falciparum
CHEMBL364
 IC50 5.52 5.515 3000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.7 nM 8.77 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.7 nM 8.77 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 14.5 nM 7.84 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 60.0 nM 7.22 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 60.2 nM 7.22 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 60.2 nM 7.22 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 110.0 nM 6.96 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 470.0 nM 6.33 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 491.2 nM 6.31 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2454.0 nM 5.61 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
Plasmodium falciparum IC50 = 3100.0 nM 5.51 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3120.0 nM 5.51 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 6750.0 nM 5.17 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 8130.0 nM 5.09 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 14600.0 nM 4.84 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 14580.0 nM 4.84 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307

Literature References

PubMed DOI Target Context # Activities
14711307 10.1021/jm0303352 Bifunctional dihydrofolate reductase-thymidylate synthase 16
11881993 10.1021/jm010131q Bifunctional dihydrofolate reductase-thymidylate synthase 9
11881993 10.1021/jm010131q Plasmodium falciparum 2
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine