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Compound Detail

CHEMBL291931

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COc1ccc(Cc2cnc(N)nc2N)cc1OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL291931
Phase Preclinical
Structure Type MOL
InChI Key XARRNBRDTOCYPU-UHFFFAOYSA-N
5
Targets
15
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

336.4
MW (Da)
2.82
ALogP
6
HBA
2
HBD
96.3
PSA (Ų)
0.72
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 C19H20N4O2
MW 336.40
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -0.29

Activity Summary

IC50 8 meas. best 7.52
Ki 7 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 Ki 8.14 6.7825 7.2 4
Dihydrofolate reductase
CHEMBL4888
 Ki 7.66 7.66 21.9 1
Bifunctional dihydrofolate reductase-thymidylate synthase
CHEMBL1939
 IC50 7.52 6.06 30.0 7
Dihydrofolate reductase
CHEMBL2902
 Ki 6.91 6.91 123.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.4 5.4 4000.0 1
Dihydrofolate reductase
CHEMBL2575
 Ki 4.74 4.74 18197.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 7.2 nM 8.14 Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR) 14711307
Dihydrofolate reductase Ki = 21.88 nM 7.66 Inhibitory activity against Escherichia coli dihydrofolate reductase 1899453
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 = 50.0 nM 7.3 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Dihydrofolate reductase Ki = 123.03 nM 6.91 Inhibitory activity against Lactobacillus casei dihydrofolate reductase 2502631
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 143.4 nM 6.84 Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 250.0 nM 6.6 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 629.8 nM 6.2 Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase Ki = 1129.6 nM 5.95 Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 2620.0 nM 5.58 In vitro antimalarial activity relative to trimethoprim against Plasmodium falci... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 3830.0 nM 5.42 In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m... 14711307
Plasmodium falciparum IC50 = 4000.0 nM 5.4 Antimicrobial activity against Plasmodium falciparum 20185316
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 5730.0 nM 5.24 In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m... 14711307
Bifunctional dihydrofolate reductase-thymidylate synthase IC50 = 17480.0 nM 4.76 In vitro antimalarial activity against Plasmodium falciparum TM4/8.2 wtDHFR 14711307
Dihydrofolate reductase Ki = 18197.01 nM 4.74 Inhibitory activity against chicken liver dihydrofolate reductase 2502631

Literature References

PubMed DOI Target Context # Activities
14711307 10.1021/jm0303352 Bifunctional dihydrofolate reductase-thymidylate synthase 16
3276891 10.1021/jm00397a017 Escherichia coli 2
2502631 10.1021/jm00128a035 Dihydrofolate reductase 2
11495588 10.1021/jm000226c Dihydrofolate reductase 1
1507206 10.1021/jm00095a016 Dihydrofolate reductase 1
1899453 10.1021/jm00105a008 Dihydrofolate reductase 1
3276891 10.1021/jm00397a017 Dihydrofolate reductase 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