Compound Detail

CHEMBL138060

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COc1ccc(OC)c(CNc2ccc3nc(N)nc(N)c3c2Cl)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL138060
Phase	Preclinical
Structure Type	MOL
InChI Key	ZQYDKYDSKVGDJP-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

359.8

MW (Da)

3.08

ALogP

HBA

HBD

108.3

PSA (Å²)

0.64

QED

Ro5 Violations

Rot. Bonds

First in Class Prodrug

IC50 9 meas. best 9.41

Ki 3 meas. best 9.41

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL1939	IC50	9.41	9.41	0.4	1
Unchecked CHEMBL612545	Ki	9.41	9.325	0.4	2
Plasmodium falciparum CHEMBL364	IC50	8.35	8.1875	4.5	4
Dihydrofolate reductase CHEMBL202	Ki	7.99	7.99	10.2	1
Bifunctional dihydrofolate reductase-thymidylate synthase CHEMBL2425	IC50	7.77	7.77	17.0	1
Dihydrofolate reductase CHEMBL2363	IC50	7.55	7.55	28.0	1
Dihydrofolate reductase CHEMBL1926	IC50	7.28	7.28	53.0	1

Parameter	Value	Units	Species
AUC	27600.0	ng.hr.mL-1	Rattus norvegicus
AUC	16990.0	ng.hr.mL-1	Mus musculus
AUC	16047.97	ng.hr.mL-1	Mus musculus
AUC	24215.89	ng.hr.mL-1	Rattus norvegicus
CL	51.06	mL.min-1.kg-1	Mus musculus
CL	17.0	mL.min-1.kg-1	Rattus norvegicus
Cmax	5100.0	nM	Mus musculus
Cmax	2800.0	nM	Rattus norvegicus
F	100.0	%	Mus musculus
F	63.0	%	Rattus norvegicus
T1/2	4.84	hr	Mus musculus
T1/2	9.3	hr	Rattus norvegicus
T1/2	0.8	hr	Mus musculus
T1/2	3.5	hr	Rattus norvegicus
Tmax	4.0	hr	Mus musculus
Tmax	4.0	hr	Rattus norvegicus
Vd	2.85	L.kg-1	Mus musculus
Vd	4.7	L.kg-1	Rattus norvegicus

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	0.39	nM	9.41	Inhibition of Plasmodium falciparum DHFR	29111368
Unchecked	Ki	=	0.39	nM	9.41	Binding affinity to wild type Plasmodium falciparum DHFR by competitive binding ...	20350951
Unchecked	Ki	=	0.58	nM	9.24	Binding affinity to recombinant Plasmodium falciparum V1/S DHFR S108N, N51I, C59...	20350951
Plasmodium falciparum	IC50	=	4.48	nM	8.35	Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum clin...	20350951
Plasmodium falciparum	IC50	=	4.48	nM	8.35	Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum clin...	20350951
Plasmodium falciparum	IC50	=	7.61	nM	8.12	Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum V1/S...	20350951
Dihydrofolate reductase	Ki	=	10.2	nM	7.99	Binding affinity to human recombinant DHFR expressed in Escherichia coli BL21(DE...	20350951
Plasmodium falciparum	IC50	=	11.66	nM	7.93	Antimalarial activity against pyrimethamine-resistant Plasmodium falciparum clin...	20350951
Bifunctional dihydrofolate reductase-thymidylate synthase	IC50	=	17.0	nM	7.77	Inhibition of Dihydrofolate reductase of Toxoplasma gondii	7799402
Dihydrofolate reductase	IC50	=	28.0	nM	7.55	Inhibition of Dihydrofolate reductase (DHFR) of in rat liver	7799402
Dihydrofolate reductase	IC50	=	53.0	nM	7.28	Inhibition of Dihydrofolate reductase of Pneumocystis carinii	7799402

PubMed	DOI	Target Context	# Activities
20350951	10.1128/aac.01526-09	Plasmodium berghei	27
20350951	10.1128/aac.01526-09	Mus musculus	17
20350951	10.1128/aac.01526-09	Rattus norvegicus	12
20350951	10.1128/aac.01526-09	Unchecked	4
20350951	10.1128/aac.01526-09	Plasmodium falciparum	4
7799402	10.1021/jm00052a011	Dihydrofolate reductase	2
7799402	10.1021/jm00052a011	Bifunctional dihydrofolate reductase-thymidylate synthase	1
7799402	10.1021/jm00052a011	Dihydrofolate reductase; P. carinii vs rat	1
7799402	10.1021/jm00052a011	Dihydrofolate reductase; T. gondii vs rat	1
20185316	10.1016/j.bmc.2010.01.068	Cryptosporidium parvum	1
20350951	10.1128/aac.01526-09	Dihydrofolate reductase	1
29111368	10.1016/j.bmc.2017.10.017	Bifunctional dihydrofolate reductase-thymidylate synthase	1

Data from ChEMBL 36 via Core Engine