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Compound Detail

CHEMBL22139

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CCCOc1cc(Cc2cnc(N)nc2N)ccc1OCc1cc(OC)c(OC)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL22139
Phase Preclinical
Structure Type MOL
InChI Key PYIOFTJOOJKVOH-UHFFFAOYSA-N
4
Targets
20
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

454.5
MW (Da)
3.63
ALogP
9
HBA
2
HBD
124.0
PSA (Ų)
0.45
QED
0
Ro5 Violations
11
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H30N4O5
MW 454.53
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -0.19

Activity Summary

IC50 13 meas. best 7.7
Ki 7 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.4 8.2686 0.4 7
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.7 6.265 20.0 8
Plasmodium falciparum
CHEMBL364
 IC50 6.82 6.82 150.0 1
Vero
CHEMBL391
 IC50 4.89 4.89 13000.0 1
BC
CHEMBL613535
 IC50 4.25 4.25 56000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.4 nM 9.4 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1.6 nM 8.8 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.5 nM 8.46 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 5.6 nM 8.25 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 20.0 nM 7.7 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 30.0 nM 7.52 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
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 = 105.6 nM 6.98 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 150.0 nM 6.82 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Plasmodium falciparum IC50 = 150.0 nM 6.82 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 258.6 nM 6.59 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4300.0 nM 5.37 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4290.0 nM 5.37 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 7700.0 nM 5.11 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 9750.0 nM 5.01 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307
Vero IC50 = 13000.0 nM 4.89 Cytotoxicity by the selective inhibition against African green monkey kidney fib... 11881993
BC IC50 = 56000.0 nM 4.25 Cytotoxicity against human breast cancer cells. 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