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Compound Detail

CHEMBL2058057

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O=c1[nH]c(-c2ccc(Br)cc2)nc2ccccc12

Basic Information

ChEMBL ID CHEMBL2058057
Phase Preclinical
Structure Type MOL
InChI Key NRCCYFAMXZIJSC-UHFFFAOYSA-N
11
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

301.1
MW (Da)
3.35
ALogP
2
HBA
1
HBD
45.8
PSA (Ų)
0.75
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H9BrN2O
MW 301.14
Aromatic Rings 3
Heavy Atoms 18
NP-Likeness -1.02

Activity Summary

IC50 15 meas. best 8.52
Ki 1 meas. best 4.97

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cytochrome P450 1B1
CHEMBL4878
IC50 8.52 7.78 3.0 3
Poly [ADP-ribose] polymerase tankyrase-1
CHEMBL6164
IC50 7.96 7.305 11.0 2
Poly [ADP-ribose] polymerase tankyrase-2
CHEMBL6154
IC50 7.0 7.0 101.0 1
Cytochrome P450 1A1
CHEMBL2231
IC50 5.82 5.455 1500.0 2
Leishmania infantum
CHEMBL612848
IC50 5.16 5.16 6890.0 1
Unchecked
CHEMBL612545
Ki 4.97 4.97 10600.0 1
COLO 205
CHEMBL614561
IC50 4.96 4.96 11000.0 1
Unchecked
CHEMBL612545
IC50 4.81 4.81 15600.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.7 4.7 19780.0 1
K562
CHEMBL385
IC50 4.68 4.68 21000.0 1
MDA-MB-231
CHEMBL400
IC50 4.39 4.39 41000.0 1
Toxoplasma gondii
CHEMBL612888
IC50 4.04 4.04 92000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cytochrome P450 1B1 IC50 = 3.0 nM 8.52 Inhibition of human CYP1B1 expressed in yeast microsomal membranes using 7-ethox... 28259840
Poly [ADP-ribose] polymerase tankyrase-1 IC50 = 11.0 nM 7.96 Inhibition of human recombinant full length TNKS1 (1030 to 1317 residues) expres... 32877803
Cytochrome P450 1B1 IC50 = 25.0 nM 7.6 Inhibition of recombinant human liver CYP1B1 expressed in HEK293 cells using 7-e... 28259840
Cytochrome P450 1B1 IC50 = 60.0 nM 7.22 Inhibition of recombinant human CYP1B1 expressed in yeast cells using 7-ethoxyre... 28259840
Poly [ADP-ribose] polymerase tankyrase-2 IC50 = 101.0 nM 7.0 Inhibition of N-terminal GST-tagged human TNKS-2 (849 to 1166 residues) expresse... 27163581
Poly [ADP-ribose] polymerase tankyrase-1 IC50 = 224.0 nM 6.65 Inhibition of TNKS-1 (unknown origin) using histone as substrate incubated for 3... 27163581
Cytochrome P450 1A1 IC50 = 1500.0 nM 5.82 Inhibition of recombinant human CYP1A1 expressed in yeast cells using 7-ethoxyre... 28259840
Leishmania infantum IC50 = 6890.0 nM 5.16 Antileishmanial activity against Leishmania infantum promastigotes 37859724
Cytochrome P450 1A1 IC50 = 8200.0 nM 5.09 Inhibition of human CYP1A1 expressed in yeast microsomal membranes using 7-ethox... 28259840
Unchecked Ki = 10600.0 nM 4.97 Non-competitive inhibition of Saccharomyces cerevisiae alpha-glucosidase type 1 ... 28110817
COLO 205 IC50 = 11000.0 nM 4.96 Antiproliferative activity against human COLO205 cells by MTT assay 22749421
Unchecked IC50 = 15600.0 nM 4.81 Inhibition of Saccharomyces cerevisiae alpha-glucosidase type 1 using p-nitro-ph... 28110817
Trypanosoma cruzi IC50 = 19780.0 nM 4.7 Antitrypanosomal activity against of Trypanosoma cruzi epimastigotes 37859724
K562 IC50 = 21000.0 nM 4.68 Antiproliferative activity against human K562 cells by MTT assay 22749421
MDA-MB-231 IC50 = 41000.0 nM 4.39 Antiproliferative activity against human MDA-MB-231 cells by MTT assay 22749421
Toxoplasma gondii IC50 = 92000.0 nM 4.04 Antiparasitic activity against tachyzoite stage of Toxoplasma gondii expressing ... 29598911

Literature References

PubMed DOI Target Context # Activities
28110817 10.1016/j.bmc.2016.09.042 Unchecked 9
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 1A1 6
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 1B1 6
29598911 10.1016/j.bmcl.2018.03.036 Toxoplasma gondii 5
27163581 10.1016/j.ejmech.2016.04.041 Poly [ADP-ribose] polymerase tankyrase-2 4
27163581 10.1016/j.ejmech.2016.04.041 HT-29 3
32631506 10.1016/j.bmcl.2020.127274 Adenosine receptor A1 2
38784470 10.1039/d3md00600j NCI-H460 2
32631506 10.1016/j.bmcl.2020.127274 Adenosine receptor A2a 2
38509663 10.1021/acs.jmedchem.4c00164 Cytochrome P450 1B1 2
38784470 10.1039/d3md00600j A2780 2
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 2C19 2
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 2C9 2
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 3A4 2
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 2D6 2
28259840 10.1016/j.ejmech.2017.02.032 Cytochrome P450 1A2 2
38784470 10.1039/d3md00600j HT-29 2
38784470 10.1039/d3md00600j U-87 MG 2
38784470 10.1039/d3md00600j A-431 2
38784470 10.1039/d3md00600j MCF7 2

Data from ChEMBL 36 via Core Engine