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Compound Detail

CHEMBL426560

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O=C(O)CNC(=O)c1nc(Cl)c2ccccc2c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL426560
Phase Preclinical
Structure Type MOL
InChI Key OUQVKRKGTAUJQA-UHFFFAOYSA-N
7
Targets
32
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

280.7
MW (Da)
1.41
ALogP
4
HBA
3
HBD
99.5
PSA (Ų)
0.74
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 C12H9ClN2O4
MW 280.67
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.56

Activity Summary

IC50 24 meas. best 7.16
Kd 5 meas. best 7.1
EC50 2 meas. best 4.19
Ki 1 meas. best 6.15

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Egl nine homolog 1
CHEMBL5697
 IC50 7.16 5.9683 70.0 12
Unchecked
CHEMBL612545
 IC50 7.14 6.215 73.0 2
Egl nine homolog 1
CHEMBL5697
 Kd 7.1 7.1 80.0 1
Gamma-butyrobetaine dioxygenase
CHEMBL3817724
 IC50 6.68 6.3 210.0 2
Prolyl 4-hydroxylase
CHEMBL4523368
 Ki 6.15 6.15 710.0 1
Alpha-ketoglutarate-dependent dioxygenase FTO
CHEMBL2331065
 IC50 5.55 5.55 2800.0 4
Prolyl 4-hydroxylase
CHEMBL4523368
 IC50 5.35 5.35 4500.0 1
Gamma-butyrobetaine dioxygenase
CHEMBL2163175
 Kd 4.89 4.89 13000.0 1
Gamma-butyrobetaine dioxygenase
CHEMBL3817724
 Kd 4.66 4.66 22000.0 1
Gamma-butyrobetaine dioxygenase
CHEMBL2163175
 IC50 4.5 4.4733 32000.0 3
Hep 3B2
CHEMBL4296437
 EC50 4.19 4.19 64000.0 1
Egl nine homolog 1
CHEMBL5697
 EC50 4.1 4.1 79000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 12.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Egl nine homolog 1 IC50 = 70.0 nM 7.16 Inhibition of human PHD2 catalytic domain (181 to 426) Mn2 expressed in Escheric... 23234607
Unchecked IC50 = 73.0 nM 7.14 Destabilizing effect on human recombinant PHD2 (181-426) expressed in Escherichi... 19364117
Egl nine homolog 1 IC50 = 73.0 nM 7.14 Inhibition of human PHD2 at 293K temperature by solvent relaxation technique 20025281
Egl nine homolog 1 Kd = 80.0 nM 7.1 Binding affinity to human PHD2 catalytic domain (181 to 426) Mn2 expressed in Es... 23234607
Gamma-butyrobetaine dioxygenase IC50 = 210.0 nM 6.68 Inhibition of Pseudomonas sp. AK1 BBOX assessed as hydroxylation of GBB to L-car... -
Egl nine homolog 1 IC50 = 300.0 nM 6.52 Inhibition of recombinant PHD2 (unknown origin) catalytic domain (181 to 426 res... 26713111
Egl nine homolog 1 IC50 = 300.0 nM 6.52 Inhibition of PHD2 (181 to 426 residues) (unknown origin) using biotinylated COD... 29259755
Egl nine homolog 1 IC50 = 424.2 nM 6.37 Displacement of FITC-HIF-1alpha (556 to 574 residues) from PHD2 (181 to 426 resi... 26713111
Egl nine homolog 1 IC50 = 640.0 nM 6.19 Inhibition of HIF-PHD2 (unknown origin) using FAM-HIF2alpha peptide incubated fo... 32676148
Prolyl 4-hydroxylase Ki = 710.0 nM 6.15 Inhibition of N-terminal His6-tagged recombinant Paramecium bursaria chlorella v... 30737136
Gamma-butyrobetaine dioxygenase IC50 = 1200.0 nM 5.92 Inhibition of Pseudomonas sp. AK1 BBOX using GBBF as substrate after 10 mins in ... -
Egl nine homolog 1 IC50 = 1400.0 nM 5.85 Inhibition of human EGLN1 16908145
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 2800.0 nM 5.55 Inhibition of FTO (unknown origin) expressed in Escherichia coli BL21(DE3) using... 38805939
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 2800.0 nM 5.55 Inhibition of FTO (unknown origin) 34792334
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 2800.0 nM 5.55 Inhibition of recombinant full length N-terminal hexahistidine-tagged human FTO ... 34762429
Alpha-ketoglutarate-dependent dioxygenase FTO IC50 = 2800.0 nM 5.55 Inhibition of human hexahistidine-tagged full-length FTO expressed in Escherichi... 23547775
Egl nine homolog 1 IC50 = 3900.0 nM 5.41 Inhibition of PHD2 (unknown origin) after 30 mins by fluorescence polarization a... 24042008
Egl nine homolog 1 IC50 = 3900.0 nM 5.41 Inhibition of PHD2 in human Hep3B cells assessed as erythropoietin secretion by ... 24894560
Egl nine homolog 1 IC50 = 3900.0 nM 5.41 Inhibition of PHD2 (unknown origin) 34792334
Prolyl 4-hydroxylase IC50 = 4500.0 nM 5.35 Inhibition of N-terminal His6-tagged recombinant Paramecium bursaria chlorella v... 30737136

Literature References

PubMed DOI Target Context # Activities
24042008 10.1016/j.bmcl.2013.08.067 Mus musculus 12
23977883 10.1021/jm400386j Homo sapiens 11
25266780 10.1016/j.bmcl.2014.09.035 Gamma-butyrobetaine dioxygenase 10
- 10.1039/C6MD00004E Gamma-butyrobetaine dioxygenase 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET1 4
24042008 10.1016/j.bmcl.2013.08.067 Egl nine homolog 1 3
38754564 10.1016/j.bmcl.2024.129799 Cynomolgus monkey 3
29259755 10.1021/acsmedchemlett.7b00404 Egl nine homolog 1 3
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET2 3
23234607 10.1021/jm301583m Egl nine homolog 1 3
23234607 10.1021/jm301583m Unchecked 3
38294854 10.1021/acs.jmedchem.3c01820 Methylcytosine dioxygenase TET3 3
19364117 10.1021/jm900285r Unchecked 2
30737136 10.1016/j.bmc.2019.01.018 Prolyl 4-hydroxylase 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
26713111 10.1021/acsmedchemlett.5b00394 Egl nine homolog 1 2
23547775 10.1021/jm400193d Alpha-ketoglutarate-dependent dioxygenase FTO 2
20025281 10.1021/jm901537q Egl nine homolog 1 2

Data from ChEMBL 36 via Core Engine