Compound Detail

CHEMBL365916

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N=C(N)c1ccc(OCc2ccc(COc3ccc(C(=N)N)cc3)cc2)cc1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL365916
Phase	Preclinical
Structure Type	MOL
InChI Key	CMQUKOACSUWXOS-UHFFFAOYSA-N

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Molecular Properties

374.4

MW (Da)

3.41

ALogP

HBA

HBD

118.2

PSA (Å²)

0.36

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Unknown
Chirality	Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula	C22H22N4O2
MW	374.44
Aromatic Rings	3
Heavy Atoms	28
NP-Likeness	-0.20

Activity Summary

IC50 10 meas. best 7.68

Ki 7 meas. best 6.5

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	7.68	7.68	20.7	1
Plasmodium falciparum CHEMBL364	IC50	7.19	7.065	64.0	2
Trypsin CHEMBL2095204	Ki	6.5	6.5	316.0	1
Coagulation factor X CHEMBL3656	Ki	6.49	6.49	327.0	1
Suppressor of tumorigenicity 14 protein CHEMBL3018	Ki	6.09	6.09	816.0	1
Prothrombin CHEMBL204	Ki	5.94	5.94	1160.0	1
Unchecked CHEMBL612545	Ki	5.89	5.89	1300.0	1
Pneumocystis carinii CHEMBL613064	IC50	5.89	5.89	1300.0	1
Leishmania donovani CHEMBL367	IC50	5.88	5.88	1320.0	1
Prothrombin CHEMBL4471	Ki	5.47	5.47	3400.0	1
Glutamate NMDA receptor CHEMBL1907608	IC50	5.28	4.9467	5240.0	3
Transmembrane protease serine 6 CHEMBL1795139	Ki	5.24	5.24	5700.0	1
L6 CHEMBL614793	IC50	4.91	4.91	12400.0	1
A549 CHEMBL392	IC50	4.52	4.52	30200.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Trypanosoma brucei rhodesiense	IC50	=	20.7	nM	7.68	Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900	19409677
Plasmodium falciparum	IC50	=	64.0	nM	7.19	Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1	19409677
Plasmodium falciparum	IC50	=	114.0	nM	6.94	Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 b...	17533134
Trypsin	Ki	=	316.0	nM	6.5	Inhibition of human trypsin using Boc-Gln-Ala-Arg-AMC as substrate after 20 mins...	27287367
Coagulation factor X	Ki	=	327.0	nM	6.49	Inhibition of bovine factor 10a using Boc-Ile-Glu-Gly-Arg-AMC as substrate after...	27287367
Suppressor of tumorigenicity 14 protein	Ki	=	816.0	nM	6.09	Inhibition of human matriptase using Boc-Gln-Ala-Arg-AMC as substrate after 20 m...	27287367
Prothrombin	Ki	=	1160.0	nM	5.94	Inhibition of human thrombin using Cbz-Gly-Gly-Arg-AMC as substrate after 20 min...	27287367
Pneumocystis carinii	IC50	=	1300.0	nM	5.89	inhibitory concentration against Pneumocystis carinii	15357989
Unchecked	Ki	=	1300.0	nM	5.89	Inhibition of bovine trypsin after 15 to 30 mins	27287367
Leishmania donovani	IC50	=	1320.0	nM	5.88	Antileishmanial activity against Leishmania donovani MHOM/SD/62/1S-CL2D amastigo...	19409677
Prothrombin	Ki	=	3400.0	nM	5.47	Inhibition of bovine thrombin using BANA/BPVANA as substrate after 15 to 40 mins	27287367
Glutamate NMDA receptor	IC50	=	5240.0	nM	5.28	Displacement of [3H]-MK-801 from rat cortical membranes NMDA receptor by beta co...	26117647
Transmembrane protease serine 6	Ki	=	5700.0	nM	5.24	Inhibition of human matriptase-2 transfected in HEK cells using Boc-Gln-Ala-Arg-...	27287367
Glutamate NMDA receptor	IC50	=	10800.0	nM	4.97	Displacement of [3H]-ifenprodil from rat cortical membranes NMDA receptor by bet...	26117647
L6	IC50	=	12400.0	nM	4.91	Cytotoxicity against rat L6 cells	19409677
Glutamate NMDA receptor	IC50	=	25700.0	nM	4.59	Displacement of [3H]-MK-801 from rat cortical membranes NMDA receptor by beta co...	26117647
A549	IC50	=	30200.0	nM	4.52	Cytotoxicity against A549 cell line	15357989

Literature References

PubMed	DOI	Target Context	# Activities
26117647	10.1016/j.bmc.2015.06.012	Glutamate NMDA receptor	4
19409677	10.1016/j.ejmech.2009.03.014	Trypanosoma brucei rhodesiense	3
19409677	10.1016/j.ejmech.2009.03.014	Unchecked	3
27287367	10.1016/j.bmcl.2016.05.071	Prothrombin	2
27287367	10.1016/j.bmcl.2016.05.071	Transmembrane protease serine 6	2
15357989	10.1016/j.bmcl.2004.06.034	Pneumocystis carinii	1
15357989	10.1016/j.bmcl.2004.06.034	A549	1
17533134	10.1016/j.bmc.2007.05.034	Plasmodium falciparum	1
19409677	10.1016/j.ejmech.2009.03.014	Plasmodium falciparum	1
19409677	10.1016/j.ejmech.2009.03.014	Leishmania donovani	1
19409677	10.1016/j.ejmech.2009.03.014	L6	1
27287367	10.1016/j.bmcl.2016.05.071	Unchecked	1
27287367	10.1016/j.bmcl.2016.05.071	Trypsin	1
27287367	10.1016/j.bmcl.2016.05.071	Coagulation factor X	1
27287367	10.1016/j.bmcl.2016.05.071	Suppressor of tumorigenicity 14 protein	1

Data from ChEMBL 36 via Core Engine