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Compound Detail

CHEMBL333985

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OCc1ccc(-c2nn(Cc3ccccc3)c3ccccc23)o1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL333985
Phase Preclinical
Structure Type MOL
InChI Key OQQVFCKUDYMWGV-UHFFFAOYSA-N
20
Targets
50
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

304.4
MW (Da)
3.84
ALogP
4
HBA
1
HBD
51.2
PSA (Ų)
0.62
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H16N2O2
MW 304.35
Aromatic Rings 4
Heavy Atoms 23
NP-Likeness -0.90

Activity Summary

IC50 49 meas. best 6.52
EC50 1 meas. best 5.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ACHN
CHEMBL614519
 IC50 6.52 6.52 300.0 1
A498
CHEMBL614516
 IC50 6.52 6.49 300.0 3
Unchecked
CHEMBL612545
 IC50 6.0 4.8 1000.0 11
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha
CHEMBL2221345
 IC50 5.92 4.9825 1200.0 4
HIF1A/p300/CREB-binding protein
CHEMBL4296108
 IC50 5.89 5.89 1300.0 1
Hypoxia-inducible factor 1-alpha
CHEMBL4261
 IC50 5.82 5.408 1500.0 5
NCI-H226
CHEMBL614740
 IC50 5.72 5.72 1900.0 1
AGS
CHEMBL613860
 IC50 5.7 5.7 2000.0 1
HCT-116
CHEMBL394
 IC50 5.66 5.66 2200.0 1
HepG2
CHEMBL395
 IC50 5.66 5.66 2200.0 1
Unchecked
CHEMBL612545
 EC50 5.39 5.39 4110.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.2 5.0667 6309.6 3
Oryctolagus cuniculus
CHEMBL374
 IC50 5.0 5.0 10000.0 1
A2780
CHEMBL614004
 IC50 4.69 4.395 20350.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.6 4.555 25300.0 2
HL-60
CHEMBL383
 IC50 4.6 4.6 25270.0 2
A549
CHEMBL392
 IC50 4.59 4.345 25620.0 2
L02
CHEMBL4296457
 IC50 4.58 4.34 26580.0 2
HeLa
CHEMBL399
 IC50 4.53 4.39 29300.0 2
cGMP-specific 3',5'-cyclic phosphodiesterase
CHEMBL1827
 IC50 4.5 4.5 31900.0 1
MCF7
CHEMBL387
 IC50 4.1 4.1 80000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 212.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
ACHN IC50 = 300.0 nM 6.52 Antitumor activity against human ACHN cells after 48 hrs by MTT assay 20097456
A498 IC50 = 300.0 nM 6.52 Cytotoxicity against human A498 cells incubated for 48 hrs by MTT assay 26235951
A498 IC50 = 300.0 nM 6.52 Cytotoxicity against human A498 cells after 48 hrs by MTT assay 26820553
A498 IC50 = 370.0 nM 6.43 Cytotoxicity against human A498 cells after 48 hrs by MTT assay 23831809
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of hypoxia-induced HIF1alpha/P300-CBP interaction mediated gene trans... 33360196
Unchecked IC50 = 1200.0 nM 5.92 Inhibition of hypoxia-induced HIF-1 transcriptional activity by luciferase repor... 21937231
Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha IC50 = 1200.0 nM 5.92 Inhibition of hypoxia-induced HIF1 transcriptional activity in human HeLa cells ... 27847273
HIF1A/p300/CREB-binding protein IC50 = 1300.0 nM 5.89 Inhibition of HIF-1alpha/p300/CBP (unknown origin) transcriptional activity expr... 29748146
Hypoxia-inducible factor 1-alpha IC50 = 1500.0 nM 5.82 Inhibition of hypoxia-induced HIF1alpha transcriptional activity in human HeLa c... 24900662
NCI-H226 IC50 = 1900.0 nM 5.72 Antitumor activity against human NCI-H226 cells after 48 hrs by MTT assay 20097456
Hypoxia-inducible factor 1-alpha IC50 = 2000.0 nM 5.7 Inhibition of hypoxia induced HIF1-alpha transcriptional activity in human AGS c... 17884495
Unchecked IC50 = 2000.0 nM 5.7 Inhibition of HIF-1 (unknown origin) expressed in human HeLa cells after 12 hrs ... -
AGS IC50 = 2000.0 nM 5.7 Inhibition of hypoxia induced HIF1 transcriptional activity in human AGS cells b... 17328532
HepG2 IC50 = 2200.0 nM 5.66 Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay 24900662
HCT-116 IC50 = 2200.0 nM 5.66 Cytotoxicity against human HCT116 cells after 72 hrs by MTT assay 24900662
Hypoxia-inducible factor 1-alpha IC50 = 2400.0 nM 5.62 Inhibition of HIF1alpha transcriptional activity in human HeLa cells transfected... 31740202
Unchecked EC50 = 4110.0 nM 5.39 Activation of sGC Enzyme (soluble Guanylate Cyclase) in Sf21 cells infected with... 11141091
Plasmodium falciparum IC50 = 6309.57 nM 5.2 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Hypoxia-inducible factor 1-alpha IC50 = 9210.0 nM 5.04 Inhibition of hypoxia-induced HIF1alpha transcriptional activity in HEK293 cells... 19435661
Unchecked IC50 = 10000.0 nM 5.0 Activation of rabbit sGC assessed as induction of preconstricted aortic ring rel... 33314936

Literature References

PubMed DOI Target Context # Activities
24480469 10.1016/j.bmcl.2014.01.015 Soluble guanylate cyclase alpha1/beta1 complex 6
11606139 10.1021/jm010001h Unchecked 4
37918036 10.1016/j.ejmech.2023.115874 Neutrophil 4
33049608 10.1016/j.ejmech.2020.112893 Unchecked 4
- 10.1039/C2MD20134H NCI-H226 3
26235951 10.1016/j.bmcl.2015.07.058 NON-PROTEIN TARGET 3
19435661 10.1016/j.bmcl.2009.04.122 Hypoxia-inducible factor 1-alpha 3
19734910 10.1038/nchembio.215 Plasmodium falciparum 3
- 10.1039/C2MD20134H NON-PROTEIN TARGET 3
17587571 10.1016/j.bmcl.2007.06.039 Unchecked 3
17884495 10.1016/j.bmcl.2007.09.005 Hypoxia-inducible factor 1-alpha 3
17189698 10.1016/j.bmc.2006.12.001 Unchecked 2
33992863 10.1016/j.bmc.2021.116214 A2780 2
33992863 10.1016/j.bmc.2021.116214 A549 2
17189698 10.1016/j.bmc.2006.12.001 HL-60 2
33992863 10.1016/j.bmc.2021.116214 Unchecked 2
27856238 10.1016/j.bmc.2016.11.007 Calcium release-activated calcium channel protein 1 2
16326101 10.1016/j.bmcl.2005.10.093 Soluble guanylate cyclase 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33992863 10.1016/j.bmc.2021.116214 L02 2

Data from ChEMBL 36 via Core Engine