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Compound Detail

CHEMBL21395

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CCOc1cc(Cc2cnc(N)nc2N)ccc1OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL21395
Phase Preclinical
Structure Type MOL
InChI Key QBQZTCRZECEEGK-UHFFFAOYSA-N
7
Targets
22
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

350.4
MW (Da)
3.21
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.68
QED
0
Ro5 Violations
7
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 -0.47

Activity Summary

IC50 12 meas. best 7.16
Ki 10 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 9.1 7.8471 0.8 7
Dihydrofolate reductase type 1
CHEMBL2627
 Ki 7.35 7.35 44.7 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.16 5.8138 70.0 8
Dihydrofolate reductase
CHEMBL2902
 Ki 6.51 6.51 309.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.3 6.3 500.0 1
Dihydrofolate reductase
CHEMBL2575
 Ki 4.74 4.74 18197.0 1
KB
CHEMBL398
 IC50 4.33 4.33 47000.0 1
BC
CHEMBL613535
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.8 nM 9.1 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 0.9 nM 9.05 Inhibition of the wild-type dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 7.1 nM 8.15 Inhibition of the S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 9.7 nM 8.01 Inhibition of the C59R+S108N mutant of dihydrofolate reductase (DHFR) 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 9.7 nM 8.01 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Dihydrofolate reductase type 1 Ki = 44.67 nM 7.35 Inhibitory activity against Escherichia coli dihydrofolate reductase 1899453
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 70.0 nM 7.16 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 120.0 nM 6.92 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 120.0 nM 6.92 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Dihydrofolate reductase Ki = 309.03 nM 6.51 Inhibitory activity against Lactobacillus casei dihydrofolate reductase 2502631
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 431.4 nM 6.37 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 470.0 nM 6.33 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Plasmodium falciparum IC50 = 500.0 nM 6.3 In vitro antiplasmodial activity (IC50) against Plasmodium falciparum wtTM4/8.2 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 570.0 nM 6.24 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 14360.0 nM 4.84 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 16600.0 nM 4.78 Antiplasmodial activity IC50 against Plasmodium falciparum K1CB1 DHFR double-mut... 11881993
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 16470.0 nM 4.78 In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 16590.0 nM 4.78 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Dihydrofolate reductase Ki = 18197.01 nM 4.74 Inhibitory activity against chicken liver dihydrofolate reductase 2502631
KB IC50 = 47000.0 nM 4.33 Cytotoxicity against human epidermoid carcinoma KB cell. 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 4
11881993 10.1021/jm010131q NON-PROTEIN TARGET 4
3934385 10.1021/jm00150a026 Escherichia coli 2
2502631 10.1021/jm00128a035 Dihydrofolate reductase 2
11495588 10.1021/jm000226c Dihydrofolate reductase 1
1899453 10.1021/jm00105a008 Dihydrofolate reductase type 1 1
1507206 10.1021/jm00095a016 Dihydrofolate reductase 1
11881993 10.1021/jm010131q Vero 1
11881993 10.1021/jm010131q KB 1
11881993 10.1021/jm010131q BC 1
2502631 10.1021/jm00128a035 No relevant target 1
20185316 10.1016/j.bmc.2010.01.068 Plasmodium falciparum 1

Data from ChEMBL 36 via Core Engine