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Compound Detail

CHEMBL48217

DAPI
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N=C(N)c1ccc(-c2cc3ccc(C(=N)N)cc3[nH]2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL48217
Name DAPI
Phase Preclinical
Structure Type MOL
InChI Key FWBHETKCLVMNFS-UHFFFAOYSA-N
9
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

277.3
MW (Da)
2.40
ALogP
2
HBA
5
HBD
115.5
PSA (Ų)
0.37
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C16H15N5
MW 277.33
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness -0.45

Activity Summary

IC50 14 meas. best 8.52
Ki 3 meas. best 5.57
Kd 1 meas. best 4.78

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Plasmodium falciparum
CHEMBL364
 IC50 8.52 8.52 3.0 3
Trypanosoma brucei rhodesiense
CHEMBL612348
 IC50 7.77 7.755 17.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.75 7.75 18.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.07 6.07 860.0 1
L6
CHEMBL614793
 IC50 6.07 6.07 860.0 4
Glandular kallikrein
CHEMBL3243909
 Ki 5.57 5.57 2700.0 1
Unchecked
CHEMBL612545
 IC50 5.55 5.55 2800.0 1
Unchecked
CHEMBL612545
 Ki 5.28 5.28 5310.0 1
Prothrombin
CHEMBL4471
 Ki 5.08 5.08 8370.0 1
Cell division protein FtsZ
CHEMBL3999
 Kd 4.78 4.78 16600.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antiparasitic activity against Plasmodium falciparum K1 21421317
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antiparasitic activity against Plasmodium falciparum K1 20031421
Plasmodium falciparum IC50 = 3.0 nM 8.52 Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum K1 18841956
Trypanosoma brucei rhodesiense IC50 = 17.0 nM 7.77 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB 900 bloods... 18841956
Trypanosoma brucei rhodesiense IC50 = 18.0 nM 7.75 Antiparasitic activity against Trypanosoma brucei rhodesiense STIB900 21421317
Trypanosoma brucei rhodesiense IC50 = 18.0 nM 7.75 Antiparasitic activity against Trypanosoma brucei rhodesiense STIB900 20031421
NON-PROTEIN TARGET IC50 = 18.0 nM 7.75 Antitrypanosomal activity against bloodstream form of Trypanosoma brucei rhodesi... 27843114
Trypanosoma brucei rhodesiense IC50 = 18.0 nM 7.75 Antitrypanosomal activity against Trypanosoma brucei rhodesiense STIB900 bloodst... 28152428
L6 IC50 = 860.0 nM 6.07 Cytotoxicity against rat L6 cells 21421317
L6 IC50 = 860.0 nM 6.07 Cytotoxicity against rat L6 cells 28152428
Rattus norvegicus IC50 = 860.0 nM 6.07 Cytotoxicity against rat L6 cells assessed as reduction in cell viability after ... 27843114
L6 IC50 = 860.0 nM 6.07 Cytotoxicity against rat L6 cells 20031421
L6 IC50 = 860.0 nM 6.07 Cytotoxicity against rat L6 cells 18841956
Glandular kallikrein Ki = 2700.0 nM 5.57 Competitive reversible inhibition of porcine pancreatic kallikrein using alpha-N... 671460
Unchecked IC50 = 2800.0 nM 5.55 Inhibition of mouse hippocampal neurons ASIC transfected in CHO cells assessed a... 24630693
Unchecked Ki = 5310.0 nM 5.28 Competitive reversible inhibition of bovine trypsin using alpha-N-benzoyl-DL-arg... 671460
Prothrombin Ki = 8370.0 nM 5.08 Competitive reversible inhibition of bovine thrombin using alpha-N-benzoyl-DL-ar... 671460
Cell division protein FtsZ Kd = 16600.0 nM 4.78 Binding affinity to Escherichia coli FtsZ by fluorescence anisotrophy 25791674

Literature References

PubMed DOI Target Context # Activities
8691476 10.1021/jm9507946 Nucleic Acid 5
18841956 10.1021/jm800918v Trypanosoma brucei rhodesiense 5
1738139 10.1021/jm00081a003 Nucleic Acid 4
19770280 10.1128/aac.00748-09 Acinetobacter baumannii 4
8510102 10.1021/jm00064a008 Nucleic Acid 4
15177454 10.1016/j.bmcl.2004.04.055 Unchecked 3
28152428 10.1016/j.ejmech.2017.01.037 Unchecked 3
671460 10.1021/jm00205a005 Plasma 3
19770280 10.1128/aac.00748-09 Escherichia coli 3
20031421 10.1016/j.bmc.2009.12.011 Unchecked 2
15177454 10.1016/j.bmcl.2004.04.055 Telomerase reverse transcriptase 2
21421317 10.1016/j.bmc.2011.02.045 Unchecked 2
18841956 10.1021/jm800918v Unchecked 2
19553111 10.1016/j.bmcl.2009.06.021 Acid-sensing ion channel 3 2
27843114 10.1016/j.bmcl.2016.11.006 Unchecked 2
25791674 10.1016/j.ejmech.2015.03.026 Cell division protein FtsZ 2
21421317 10.1016/j.bmc.2011.02.045 Trypanosoma brucei rhodesiense 2
18841956 10.1021/jm800918v Plasmodium falciparum 1
8510102 10.1021/jm00064a008 Calf thymus DNA 1
18841956 10.1021/jm800918v L6 1

Data from ChEMBL 36 via Core Engine