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Compound Detail

CHEMBL3727577

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Cc1cnc(Cl)nc1-c1ccc(N(Cc2ccc(CNC(=O)C(F)F)cc2)C(=O)c2ccc(O)cc2O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3727577
Phase Preclinical
Structure Type MOL
InChI Key LCGNLQSOSJFLKR-UHFFFAOYSA-N
5
Targets
24
Activities
4
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

553.0
MW (Da)
5.24
ALogP
6
HBA
3
HBD
115.7
PSA (Ų)
0.26
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C28H23ClF2N4O4
MW 552.97
Aromatic Rings 4
Heavy Atoms 39
NP-Likeness -1.12

Activity Summary

IC50 19 meas. best 8.0
EC50 3 meas. best 7.46
Kd 1 meas. best 6.82
Ki 1 meas. best 7.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
CHEMBL4766
 IC50 8.0 7.23 10.0 7
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial
CHEMBL4141
 IC50 7.68 7.04 21.0 4
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial
CHEMBL3893
 IC50 7.58 7.17 26.0 4
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
CHEMBL4766
 Ki 7.55 7.55 28.0 1
Unchecked
CHEMBL612545
 EC50 7.46 7.19 35.0 2
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
CHEMBL4766
 EC50 7.21 7.21 62.0 1
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial
CHEMBL3861
 IC50 7.19 7.065 65.0 4
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial
CHEMBL4766
 Kd 6.82 6.82 150.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 10.0 nM 8.0 Inhibition of pyruvate dehydrogenase kinase 1 (unknown origin) assessed as reduc... -
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial IC50 = 21.0 nM 7.68 Inhibition of PDHK4 (unknown origin) by radiometric biochemical kinase assay 31469962
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial IC50 = 26.0 nM 7.58 Inhibition of PDHK3 (unknown origin) by radiometric biochemical kinase assay 31469962
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Ki = 28.0 nM 7.55 Inhibition of fluorescein-labelled VER160364 binding to PDHK1 (unknown origin) a... 28199108
Unchecked EC50 = 35.0 nM 7.46 Inhibition of PDK (unknown origin) 37688544
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 35.0 nM 7.46 Inhibition of PDHK1 (unknown origin) assessed as decrease in phosphorylation of ... 28199108
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 35.0 nM 7.46 Inhibition of human recombinant PDHK1 co-complexed with porcine PDH using sodium... 34808405
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial IC50 = 40.0 nM 7.4 Inhibition of PDHK3 (unknown origin) assessed as decrease in phosphorylation of ... 28199108
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 42.0 nM 7.38 Inhibition of PDHK1 (unknown origin) by radiometric biochemical kinase assay 31469962
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial EC50 = 62.0 nM 7.21 Inhibition of PDK1 (unknown origin) incubated for 30 mins in presence of ATP by ... 37688544
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial IC50 = 65.0 nM 7.19 Inhibition of PDHK2 (unknown origin) by radiometric biochemical kinase assay 31469962
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial IC50 = 80.0 nM 7.1 Inhibition of recombinant human His-tagged PDK2 expressed in Escherichia coli us... 30597326
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial IC50 = 84.0 nM 7.08 Inhibition of PDHK2 (unknown origin) assessed as decrease in phosphorylation of ... 28199108
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 90.0 nM 7.05 Inhibition of recombinant human His-tagged PDK1 expressed in Escherichia coli us... 30597326
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial IC50 = 91.0 nM 7.04 Inhibition of PDHK4 (unknown origin) assessed as decrease in phosphorylation of ... 28199108
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial IC50 = 95.7 nM 7.02 Inhibition of PDK1 (unknown origin) using PDC E1 as substrate measured after 30 ... 30568752
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of recombinant human His-tagged PDK3 expressed in Escherichia coli us... 30597326
Unchecked EC50 = 120.0 nM 6.92 Inhibition of porcine PDK assessed as activation of pyruvate dehydrogenase compl... 30597326
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial IC50 = 130.0 nM 6.89 Inhibition of PDK2 (unknown origin) using PDC E1 as substrate measured after 30 ... 30568752
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial IC50 = 150.0 nM 6.82 Inhibition of recombinant human His-tagged PDK4 expressed in Escherichia coli us... 30597326

Literature References

PubMed DOI Target Context # Activities
28199108 10.1021/acs.jmedchem.6b01478 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial 5
30597326 10.1016/j.ejmech.2018.12.051 Unchecked 3
30568752 10.1039/C8MD00453F NCI-H1975 2
28199108 10.1021/acs.jmedchem.6b01478 Heat shock protein HSP 90-alpha 1
28199108 10.1021/acs.jmedchem.6b01478 Heat shock protein HSP90 1
37688544 10.1021/acs.jmedchem.3c01197 Unchecked 1
31469962 10.1021/acs.jmedchem.9b00565 NCI-H1299 1
31469962 10.1021/acs.jmedchem.9b00565 Heat shock protein HSP90 1
31469962 10.1021/acs.jmedchem.9b00565 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial 1
31469962 10.1021/acs.jmedchem.9b00565 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial 1
31469962 10.1021/acs.jmedchem.9b00565 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial 1
31469962 10.1021/acs.jmedchem.9b00565 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial 1
30568752 10.1039/C8MD00453F Pyruvate dehydrogenase kinase 1
30568752 10.1039/C8MD00453F [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial 1
30568752 10.1039/C8MD00453F [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial 1
30568752 10.1039/C8MD00453F [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial 1
30568752 10.1039/C8MD00453F [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial 1
28199108 10.1021/acs.jmedchem.6b01478 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 4, mitochondrial 1
28199108 10.1021/acs.jmedchem.6b01478 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 3, mitochondrial 1
28199108 10.1021/acs.jmedchem.6b01478 [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial 1

Data from ChEMBL 36 via Core Engine