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Compound Detail

CHEMBL181480

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N=C(N)c1ccc(OCc2ccccc2COc2ccc(C(=N)N)cc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL181480
Phase Preclinical
Structure Type MOL
InChI Key DBQNFQRZGKINAU-UHFFFAOYSA-N
12
Targets
15
Activities
2
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

374.4
MW (Da)
3.41
ALogP
4
HBA
4
HBD
118.2
PSA (Ų)
0.36
QED
0
Ro5 Violations
8
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 -0.27

Activity Summary

IC50 10 meas. best 6.84
Ki 5 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 6.84 6.84 144.0 1
Plasmodium falciparum
CHEMBL364
 IC50 6.82 6.66 153.0 2
Trypsin
CHEMBL2095204
 Ki 6.66 6.66 221.0 1
Prothrombin
CHEMBL204
 Ki 6.55 6.55 279.0 1
Glutamate NMDA receptor
CHEMBL1907608
 IC50 5.85 5.65 1420.0 3
Pneumocystis carinii
CHEMBL613064
 IC50 5.85 5.85 1400.0 1
Suppressor of tumorigenicity 14 protein
CHEMBL3018
 Ki 5.64 5.64 2280.0 1
Leishmania donovani
CHEMBL367
 IC50 5.42 5.42 3820.0 1
Transmembrane protease serine 6
CHEMBL1795139
 Ki 5.28 5.28 5200.0 1
Coagulation factor X
CHEMBL3656
 Ki 4.86 4.86 13700.0 1
L6
CHEMBL614793
 IC50 4.52 4.52 30100.0 1
A549
CHEMBL392
 IC50 4.48 4.48 33100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trypanosoma brucei rhodesiense IC50 = 144.0 nM 6.84 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900 19409677
Plasmodium falciparum IC50 = 153.0 nM 6.82 Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 19409677
Trypsin Ki = 221.0 nM 6.66 Inhibition of human trypsin using Boc-Gln-Ala-Arg-AMC as substrate after 20 mins... 27287367
Prothrombin Ki = 279.0 nM 6.55 Inhibition of human thrombin using Cbz-Gly-Gly-Arg-AMC as substrate after 20 min... 27287367
Plasmodium falciparum IC50 = 313.0 nM 6.5 Antiplasmodial activity against chloroquine-sensitive Plasmodium falciparum D6 b... 17533134
Pneumocystis carinii IC50 = 1400.0 nM 5.85 inhibitory concentration against Pneumocystis carinii 15357989
Glutamate NMDA receptor IC50 = 1420.0 nM 5.85 Displacement of [3H]-ifenprodil from rat cortical membranes NMDA receptor by bet... 26117647
Glutamate NMDA receptor IC50 = 1460.0 nM 5.84 Displacement of [3H]-MK-801 from rat cortical membranes NMDA receptor by beta co... 26117647
Suppressor of tumorigenicity 14 protein Ki = 2280.0 nM 5.64 Inhibition of human matriptase using Boc-Gln-Ala-Arg-AMC as substrate after 20 m... 27287367
Leishmania donovani IC50 = 3820.0 nM 5.42 Antileishmanial activity against Leishmania donovani MHOM/SD/62/1S-CL2D amastigo... 19409677
Transmembrane protease serine 6 Ki = 5200.0 nM 5.28 Inhibition of human matriptase-2 transfected in HEK cells using Boc-Gln-Ala-Arg-... 27287367
Glutamate NMDA receptor IC50 = 5540.0 nM 5.26 Displacement of [3H]-MK-801 from rat cortical membranes NMDA receptor by beta co... 26117647
Coagulation factor X Ki = 13700.0 nM 4.86 Inhibition of bovine factor 10a using Boc-Ile-Glu-Gly-Arg-AMC as substrate after... 27287367
L6 IC50 = 30100.0 nM 4.52 Cytotoxicity against rat L6 cells 19409677
A549 IC50 = 33100.0 nM 4.48 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 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 Trypsin 1
27287367 10.1016/j.bmcl.2016.05.071 Coagulation factor X 1
27287367 10.1016/j.bmcl.2016.05.071 Prothrombin 1
27287367 10.1016/j.bmcl.2016.05.071 Suppressor of tumorigenicity 14 protein 1

Data from ChEMBL 36 via Core Engine