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Compound Detail

CHEMBL587606

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Br.CC1(C)NC(N)=NC(=N)N1OCCCSc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL587606
Phase Preclinical
Structure Type MOL
InChI Key AEJSISLMUQBCIK-UHFFFAOYSA-N
Parent Compound CHEMBL580950
Active Moiety CHEMBL580950
4
Targets
14
Activities
2
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

307.4
MW (Da)
1.99
ALogP
5
HBA
3
HBD
86.7
PSA (Ų)
0.55
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 C14H22BrN5OS
MW 388.33
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.43

Activity Summary

IC50 7 meas. best 9.28
Ki 7 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 9.52 9.27 0.3 6
Plasmodium falciparum
CHEMBL364
 IC50 9.28 8.24 0.5 6
Dihydrofolate reductase
CHEMBL202
 Ki 4.54 4.54 29100.0 1
Vero
CHEMBL391
 IC50 4.2 4.2 63800.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 0.3 nM 9.52 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N mutant expressed in Esc... 32294614
Unchecked Ki = 0.4 nM 9.4 Inhibition of Plasmodium falciparum DHFR C59R/S108N/I164L mutant expressed in Es... 32294614
Unchecked Ki = 0.5 nM 9.3 Inhibition of Plasmodium falciparum DHFR expressed in Escherichia coli BL21 usin... 32294614
Unchecked Ki = 0.5 nM 9.3 Inhibition of Plasmodium falciparum DHFR N51I/C59R/S108N/I164L mutant expressed ... 32294614
Plasmodium falciparum IC50 = 0.52 nM 9.28 Antimalarial activity against Plasmodium falciparum TM4/8.2 infected in human er... 32294614
Plasmodium falciparum IC50 = 0.58 nM 9.24 Antimalarial activity against Plasmodium falciparum T9/94 RC17 harboring DHFR A1... 32294614
Unchecked Ki = 0.8 nM 9.1 Inhibition of Plasmodium falciparum DHFR C59R/S108T mutant expressed in Escheric... 32294614
Unchecked Ki = 1.0 nM 9.0 Inhibition of Plasmodium falciparum DHFR A16V/S108T mutant expressed in Escheric... 32294614
Plasmodium falciparum IC50 = 4.8 nM 8.32 Antimalarial activity against Plasmodium falciparum K1CB1 harboring DHFR C59R/S1... 32294614
Plasmodium falciparum IC50 = 9.9 nM 8.0 Antimalarial activity against Plasmodium falciparum W2 harboring DHFR N51I/C59R/... 32294614
Plasmodium falciparum IC50 = 39.0 nM 7.41 Antimalarial activity against Plasmodium falciparum CsI-2 harboring DHFR C59R/S1... 32294614
Plasmodium falciparum IC50 = 64.0 nM 7.19 Antimalarial activity against Plasmodium falciparum V1/S harboring DHFR N51I/C59... 32294614
Dihydrofolate reductase Ki = 29100.0 nM 4.54 Inhibition of human DHFR expressed in Escherichia coli BL21 using DHF as substra... 32294614
Vero IC50 = 63800.0 nM 4.2 Cytotoxicity against African green monkey Vero cells assessed as reduction in ce... 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 Unchecked 1
20485427 10.1038/nature09107 HepG2 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