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Compound Detail

CHEMBL528489

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Br.CC1(C)NC(N)=NC(=N)N1OCCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL528489
Phase Preclinical
Structure Type MOL
InChI Key WHDZLWUOXFYAMG-UHFFFAOYSA-N
Parent Compound CHEMBL535224
Active Moiety CHEMBL535224
4
Targets
13
Activities
2
Assay Types
0
PK Parameters
11
Publications
0
Known Names

Molecular Properties

261.3
MW (Da)
1.05
ALogP
4
HBA
3
HBD
86.7
PSA (Ų)
0.76
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C13H20BrN5O
MW 342.24
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 0.15

Activity Summary

Ki 7 meas. best 8.96
IC50 6 meas. best 7.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.96 8.34 1.1 6
Plasmodium falciparum
CHEMBL364
 IC50 7.52 6.842 30.0 5
Vero
CHEMBL391
 IC50 4.92 4.92 12000.0 1
Dihydrofolate reductase
CHEMBL202
 Ki 4.37 4.37 42900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 1.1 nM 8.96 Inhibition of Plasmodium falciparum DHFR expressed in Escherichia coli BL21 usin... 32294614
Unchecked Ki = 2.0 nM 8.7 Inhibition of Plasmodium falciparum DHFR C59R/S108T mutant expressed in Escheric... 32294614
Unchecked Ki = 2.9 nM 8.54 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N mutant expressed in Esc... 32294614
Unchecked Ki = 7.1 nM 8.15 Inhibition of Plasmodium falciparum DHFR A16V/S108T mutant expressed in Escheric... 32294614
Unchecked Ki = 12.0 nM 7.92 Inhibition of Plasmodium falciparum DHFR C59R/S108N/I164L mutant expressed in Es... 32294614
Unchecked Ki = 17.0 nM 7.77 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N/I164L mutant expressed ... 32294614
Plasmodium falciparum IC50 = 30.0 nM 7.52 Antimalarial activity against Plasmodium falciparum TM4/8.2 infected in human er... 32294614
Plasmodium falciparum IC50 = 39.0 nM 7.41 Antimalarial activity against Plasmodium falciparum K1CB1 harboring DHFR C59R/S1... 32294614
Plasmodium falciparum IC50 = 240.0 nM 6.62 Antimalarial activity against Plasmodium falciparum W2 harboring DHFR N51I/C59R/... 32294614
Plasmodium falciparum IC50 = 300.0 nM 6.52 Antimalarial activity against Plasmodium falciparum CsI-2 harboring DHFR C59R/S1... 32294614
Plasmodium falciparum IC50 = 720.0 nM 6.14 Antimalarial activity against Plasmodium falciparum V1/S harboring DHFR N51I/C59... 32294614
Vero IC50 = 12000.0 nM 4.92 Cytotoxicity against African green monkey Vero cells assessed as reduction in ce... 32294614
Dihydrofolate reductase Ki = 42900.0 nM 4.37 Inhibition of human DHFR expressed in Escherichia coli BL21 using DHF as substra... 32294614

Literature References

PubMed DOI Target Context # Activities
32294614 10.1016/j.ejmech.2020.112263 Unchecked 9
32294614 10.1016/j.ejmech.2020.112263 Plasmodium falciparum 6
20485427 10.1038/nature09107 Plasmodium falciparum 4
32294614 10.1016/j.ejmech.2020.112263 ADMET 3
20485427 10.1038/nature09107 HepG2 1
20485427 10.1038/nature09107 Unchecked 1
- 10.6019/CHEMBL3433997 Solute carrier family 2, facilitated glucose transporter member 1 1
- 10.6019/CHEMBL3433997 Hexose transporter 1 1
- 10.6019/CHEMBL3433997 Glucose transporter 1
32294614 10.1016/j.ejmech.2020.112263 Dihydrofolate reductase 1
32294614 10.1016/j.ejmech.2020.112263 Vero 1

Data from ChEMBL 36 via Core Engine