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Compound Detail

CHEMBL22901

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CCOc1cc(Cc2cnc(N)nc2N)ccc1OCc1cc(OC)c(OC)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22901
Phase Preclinical
Structure Type MOL
InChI Key UZYFAUNKCDIOLM-UHFFFAOYSA-N
3
Targets
20
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

440.5
MW (Da)
3.24
ALogP
9
HBA
2
HBD
124.0
PSA (Ų)
0.49
QED
0
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C23H28N4O5
MW 440.50
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.23

Activity Summary

IC50 13 meas. best 8.0
Ki 7 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.52 8.5186 0.3 7
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 8.0 6.2138 10.0 8
Plasmodium falciparum
CHEMBL364
 IC50 7.16 7.16 70.0 1
Vero
CHEMBL391
 IC50 4.47 4.47 34000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.3 nM 9.52 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.3 nM 9.52 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.8 nM 8.74 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 2.2 nM 8.66 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 10.0 nM 8.0 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 24.7 nM 7.61 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 40.0 nM 7.4 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 70.0 nM 7.16 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Plasmodium falciparum IC50 = 70.0 nM 7.16 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 110.0 nM 6.96 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 119.3 nM 6.92 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 5000.0 nM 5.3 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 5010.0 nM 5.3 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 13150.0 nM 4.88 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 19450.0 nM 4.71 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307
Vero IC50 = 34000.0 nM 4.47 Cytotoxicity by the selective inhibition against African green monkey kidney fib... 11881993

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 5
11881993 10.1021/jm010131q NON-PROTEIN TARGET 3
11881993 10.1021/jm010131q Dihydrofolate reductase 1
11881993 10.1021/jm010131q Vero 1
11881993 10.1021/jm010131q KB 1
11881993 10.1021/jm010131q BC 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine