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Compound Detail

CHEMBL120123

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COc1cc(Cc2c(C)nc(N)nc2N)ccc1OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL120123
Phase Preclinical
Structure Type MOL
InChI Key XUXCUUNKVTWVAK-UHFFFAOYSA-N
2
Targets
12
Activities
2
Assay Types
0
PK Parameters
2
Publications
0
Known Names

Molecular Properties

350.4
MW (Da)
3.13
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.71
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 C20H22N4O2
MW 350.42
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.48

Activity Summary

IC50 8 meas. best 7.7
Ki 4 meas. best 8.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.47 7.4325 3.4 4
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.7 5.8671 20.0 7
Plasmodium falciparum
CHEMBL364
 IC50 5.52 5.52 3000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 3.4 nM 8.47 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 20.0 nM 7.7 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 66.3 nM 7.18 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 89.5 nM 7.05 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 93.4 nM 7.03 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 180.0 nM 6.75 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 1030.0 nM 5.99 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2850.0 nM 5.54 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Plasmodium falciparum IC50 = 3000.0 nM 5.52 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 4820.0 nM 5.32 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 6840.0 nM 5.17 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 25240.0 nM 4.6 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
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine