Compound Detail

CHEMBL274031

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Nc1ncc(Cc2cccc(OCc3ccccc3)c2)c(N)n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL274031
Phase	Preclinical
Structure Type	MOL
InChI Key	PUMGLGGVAIIWCB-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

306.4

MW (Da)

2.81

ALogP

HBA

HBD

87.0

PSA (Å²)

0.76

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C18H18N4O
MW	306.37
Aromatic Rings	3
Heavy Atoms	23
NP-Likeness	-0.52

Activity Summary

Ki 12 meas. best 8.2

IC50 9 meas. best 7.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL1939	Ki	8.2	6.945	6.3	4
Dihydrofolate reductase CHEMBL202	Ki	7.96	6.9625	11.0	4
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL1939	IC50	7.52	5.9029	30.0	7
Dihydrofolate reductase CHEMBL1809	Ki	6.99	6.99	102.3	1
Dihydrofolate reductase CHEMBL4888	Ki	6.99	6.99	102.3	1
Dihydrofolate reductase CHEMBL2902	Ki	6.15	6.15	708.0	1
Dihydrofolate reductase CHEMBL2575	Ki	5.63	5.63	2344.2	1
Plasmodium falciparum CHEMBL364	IC50	5.52	5.52	3000.0	1
Trypanosoma brucei CHEMBL612849	IC50	5.3	5.3	5000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase	Ki	=	6.3	nM	8.2	Inhibitory activity against wild-type dihydrofolate reductase (S108N DHFR)	14711307
Dihydrofolate reductase	Ki	=	11.0	nM	7.96	Inhibition of recombinant Dihydrofolate reductase from humans.	10543874
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	30.0	nM	7.52	In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m...	14711307
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	30.0	nM	7.52	In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m...	14711307
Dihydrofolate reductase	Ki	=	65.0	nM	7.19	Inhibition of recombinant Dihydrofolate reductase from Leishmania major.	10543874
Dihydrofolate reductase	Ki	=	102.33	nM	6.99	Inhibitory activity against Escherichia coli dihydrofolate reductase	1899453
Dihydrofolate reductase	Ki	=	102.33	nM	6.99	Inhibition constant against binding of Escherichia coli dihydrofolate reductase	3290487
Bifunctional dihydrofolate reductase-thymidylate synthase	Ki	=	113.5	nM	6.95	Inhibitory activity against double mutant dihydrofolate reductase (C59R+S108N DH...	14711307
Dihydrofolate reductase	Ki	=	200.0	nM	6.7	Inhibition of recombinant Dihydrofolate reductase from Trypanosoma cruzi.	10543874
Bifunctional dihydrofolate reductase-thymidylate synthase	Ki	=	455.5	nM	6.34	Inhibitory activity against quadruple mutant dihydrofolate reductase (N51I C59R ...	14711307
Bifunctional dihydrofolate reductase-thymidylate synthase	Ki	=	515.4	nM	6.29	Inhibitory activity against triple mutant dihydrofolate reductase (C59R S108N I1...	14711307
Dihydrofolate reductase	Ki	=	707.95	nM	6.15	Inhibitory activity against Lactobacillus casei dihydrofolate reductase	2502631
Dihydrofolate reductase	Ki	=	1000.0	nM	6.0	Inhibition of recombinant Dihydrofolate reductase from humans.	10543874
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	2280.0	nM	5.64	In vitro antimalarial activity relative to trimethoprim against Plasmodium falci...	14711307
Dihydrofolate reductase	Ki	=	2344.23	nM	5.63	Inhibitory activity against chicken liver dihydrofolate reductase	2502631
Plasmodium falciparum	IC50	=	3000.0	nM	5.52	Antimicrobial activity against Plasmodium falciparum	20185316
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	3330.0	nM	5.48	In vitro antimalarial activity against Plasmodium falciparum Csl-2 triple DHFR m...	14711307
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	3520.0	nM	5.45	In vitro antimalarial activity against Plasmodium falciparum K1CB1 double DHFR m...	14711307
Trypanosoma brucei	IC50	=	5000.0	nM	5.3	Inhibition of Trypanosoma brucei rhodesiense growth	10543874
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	12750.0	nM	4.89	In vitro antimalarial activity against Plasmodium falciparum Vl/S with quadruple...	14711307

Literature References

PubMed	DOI	Target Context	# Activities
14711307	10.1021/jm0303352	Bifunctional dihydrofolate reductase-thymidylate synthase	16
10543874	10.1021/jm981130+	Dihydrofolate reductase	4
7069722	10.1021/jm00346a020	Dihydrofolate reductase	4
10543874	10.1021/jm981130+	Trypanosoma cruzi	4
7086836	10.1021/jm00347a007	L5178Y	2
2502631	10.1021/jm00128a035	Dihydrofolate reductase	2
7005446	10.1021/jm00185a011	Dihydrofolate reductase	2
6809941	10.1021/jm00349a003	Dihydrofolate reductase	2
7017146	10.1021/jm00137a012	Dihydrofolate reductase	2
11495588	10.1021/jm000226c	Dihydrofolate reductase	1
458817	10.1021/jm00192a003	Dihydrofolate reductase	1
3701780	10.1021/jm00155a006	Dihydrofolate reductase	1
3701780	10.1021/jm00155a006	No relevant target	1
7277386	10.1021/jm00139a010	Dihydrofolate reductase	1
3882967	10.1021/jm00381a013	Dihydrofolate reductase type 1	1
10543874	10.1021/jm981130+	Trypanosoma brucei	1
1899453	10.1021/jm00105a008	Dihydrofolate reductase	1
3276891	10.1021/jm00397a017	Dihydrofolate reductase	1
10543874	10.1021/jm981130+	MRC5	1
10543874	10.1021/jm981130+	Leishmania infantum	1

Data from ChEMBL 36 via Core Engine