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Compound Detail

CHEMBL472879

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Cc1nc(-c2ccccn2)nc(NCCc2ccccc2)c1Cl

Basic Information

ChEMBL ID CHEMBL472879
Phase Preclinical
Structure Type MOL
InChI Key HIUOABSWQSUEGK-UHFFFAOYSA-N
9
Targets
25
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

324.8
MW (Da)
4.16
ALogP
4
HBA
1
HBD
50.7
PSA (Ų)
0.77
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H17ClN4
MW 324.81
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -1.42

Activity Summary

IC50 14 meas. best 6.96
EC50 8 meas. best 6.72
Ki 3 meas. best 6.29

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 6.96 5.5975 110.0 4
Methionine aminopeptidase 1
CHEMBL2474
EC50 6.72 5.8967 190.0 3
Leishmania donovani
CHEMBL367
IC50 6.3 6.3 500.0 1
Unchecked
CHEMBL612545
Ki 6.29 5.8633 510.0 3
Methionine aminopeptidase 1
CHEMBL2474
IC50 6.16 6.115 700.0 2
Plasmodium falciparum
CHEMBL364
IC50 6.05 5.5925 900.0 4
Plasmodium falciparum
CHEMBL364
EC50 5.9 5.86 1251.0 2
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.44 5.44 3600.0 1
Methionine aminopeptidase 2
CHEMBL3922
IC50 5.16 5.105 7000.0 2
HeLa
CHEMBL399
EC50 5.15 5.15 7100.0 1
HUVEC
CHEMBL613979
EC50 4.96 4.96 11000.0 1
L6
CHEMBL614793
IC50 4.59 4.59 25500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 110.0 nM 6.96 Inhibition of GST-tagged Plasmodium falciparum MetAP 1B by Bradford assay 19091562
Methionine aminopeptidase 1 EC50 = 190.0 nM 6.72 Inhibition of human methionine aminopeptidase 1 in presence of Co2+ 23634668
Leishmania donovani IC50 = 500.0 nM 6.3 Antileishmanial activity against Leishmania donovani 19091562
Unchecked Ki = 510.0 nM 6.29 Inhibition of Vibrio cholerae MetAp1a by Morrison method 33035924
Methionine aminopeptidase 1 IC50 = 700.0 nM 6.16 Inhibition of HuMetAP1 using Met-Pro-pNA as substrate by spectrophotometer based... 33534577
Methionine aminopeptidase 1 EC50 = 710.0 nM 6.15 Inhibition of human methionine aminopeptidase 1 in presence of Zn2+ 23634668
Methionine aminopeptidase 1 IC50 = 860.0 nM 6.07 Inhibition of human recombinant full-length cytosolic METAP1 expressed in Escher... 23507151
Plasmodium falciparum IC50 = 900.0 nM 6.05 Antimalarial activity against multidrug resistant Plasmodium falciparum Dd2 incu... 33534577
Plasmodium falciparum EC50 = 1251.0 nM 5.9 NOVARTIS: Inhibition of Plasmodium falciparum 3D7 (drug-susceptible) proliferati... 18579783
Unchecked Ki = 1340.0 nM 5.87 Inhibition of human MetAp1a by Morrison method 33035924
Plasmodium falciparum EC50 = 1508.0 nM 5.82 NOVARTIS: Inhibition of Plasmodium falciparum W2 (drug-resistant) proliferation ... 18579783
Plasmodium falciparum IC50 = 1591.0 nM 5.8 Antimalarial activity against Plasmodium falciparum 3D7 CQ-sensitive incubated f... 33534577
Plasmodium falciparum IC50 = 3100.0 nM 5.51 Antimalarial activity against chloroquine-resistant Plasmodium falciparum Dd2 af... 19091562
NON-PROTEIN TARGET EC50 = 3600.0 nM 5.44 Antiproliferative activity against HDFa cells after 30 hrs by [3H]-thymidine inc... 23634668
Unchecked Ki = 3730.0 nM 5.43 Inhibition of Vibrio parahaemolyticus MetAp1a by Morrison method 33035924
Unchecked IC50 = 4650.0 nM 5.33 Inhibition of full length human MetAP1b using methionine para-nitroamilide as su... 23767698
Methionine aminopeptidase 2 IC50 = 7000.0 nM 5.16 Inhibition of HuMetAP2 using Met-Pro-pNA as substrate by spectrophotometer based... 33534577
HeLa EC50 = 7100.0 nM 5.15 Antiproliferative activity against human HeLa cells after 30 hrs by [3H]-thymidi... 23634668
Unchecked IC50 = 7770.0 nM 5.11 Inhibition of Enterococcus faecalis MetAP1a using methionine para-nitroamilide a... 23767698
Methionine aminopeptidase 2 IC50 = 9000.0 nM 5.05 Inhibition of human recombinant GST-6XHis-tagged full-length cytosolic METAP2 ex... 23507151

Literature References

PubMed DOI Target Context # Activities
23634668 10.1021/jm400227z Methionine aminopeptidase 1 14
23767698 10.1021/jm400395p Unchecked 5
30523084 10.1126/science.aat9446 Plasmodium berghei 4
33035924 10.1016/j.ejmech.2020.112883 Unchecked 3
23634668 10.1021/jm400227z HUVEC 2
33534577 10.1021/acs.jmedchem.0c01721 Plasmodium falciparum 2
30523084 10.1126/science.aat9446 HepG2-CD81 2
18579783 10.1073/pnas.0802982105 Plasmodium falciparum 2
19091562 10.1016/j.bmcl.2008.11.098 Plasmodium falciparum 2
22096101 10.1126/science.1211936 Plasmodium yoelii 1
18579783 10.1073/pnas.0802982105 Unchecked 1
23634668 10.1021/jm400227z No relevant target 1
19091562 10.1016/j.bmcl.2008.11.098 L6 1
23634668 10.1021/jm400227z NON-PROTEIN TARGET 1
23634668 10.1021/jm400227z HeLa 1
23507151 10.1016/j.bmc.2013.02.023 Unchecked 1
23507151 10.1016/j.bmc.2013.02.023 Methionine aminopeptidase 2 1
33534577 10.1021/acs.jmedchem.0c01721 Plasmodium yoelii 1
18579783 10.1073/pnas.0802982105 Huh-7 1
19091562 10.1016/j.bmcl.2008.11.098 Unchecked 1

Data from ChEMBL 36 via Core Engine