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Compound Detail

CHEMBL4065858

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O=C1N[C@](c2ccc(N3CCOCC3)cc2)(c2ccsc2)CC(O)=C1Sc1ccccc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4065858
Phase Preclinical
Structure Type MOL
InChI Key SUFXXEIVBZJOAP-RUZDIDTESA-N
7
Targets
16
Activities
2
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

499.1
MW (Da)
5.56
ALogP
6
HBA
2
HBD
61.8
PSA (Ų)
0.48
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C25H23ClN2O3S2
MW 499.06
Aromatic Rings 3
Heavy Atoms 33
NP-Likeness -1.29

Activity Summary

IC50 13 meas. best 8.52
EC50 3 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L-lactate dehydrogenase A chain
CHEMBL4835
 IC50 8.52 6.8575 3.0 4
L-lactate dehydrogenase B chain
CHEMBL4940
 IC50 8.3 7.33 5.0 2
L-lactate dehydrogenase A chain
CHEMBL4835
 EC50 8.14 7.3633 7.2 3
A549
CHEMBL392
 IC50 6.44 6.44 360.0 1
MIA PaCa-2
CHEMBL614725
 IC50 6.32 6.115 480.0 2
MG-63
CHEMBL614347
 IC50 6.18 6.18 660.0 1
L-lactate dehydrogenase
CHEMBL4105929
 IC50 6.06 5.95 877.0 2
A673
CHEMBL614517
 IC50 5.58 5.58 2630.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 748.59 ng.hr.mL-1 Mus musculus
AUC 2545.21 ng.hr.mL-1 Mus musculus
AUC 62382.5 ng.hr.mL-1 Mus musculus
AUC 124765.0 ng.hr.mL-1 Mus musculus
AUC 201121.18 ng.hr.mL-1 Mus musculus
CL 21.1 mL.min-1.kg-1 Mus musculus
Cmax 2500.0 nM Mus musculus
Cmax 1700.0 nM Mus musculus
Cmax 60700.0 nM Mus musculus
Cmax 224000.0 nM Mus musculus
Cmax 440000.0 nM Mus musculus
F 70.0 % Mus musculus
T1/2 1.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L-lactate dehydrogenase A chain IC50 = 3.0 nM 8.52 Inhibition of human recombinant carboxy-terminal His-tagged LDHA by UV endpoint ... 27774125
L-lactate dehydrogenase B chain IC50 = 5.0 nM 8.3 Inhibition of human recombinant carboxy-terminal His-tagged LDHB by UV endpoint ... 27774125
L-lactate dehydrogenase A chain EC50 = 7.2 nM 8.14 Inhibition of human LDH5 using pyruvate as substrate after 10 mins 29861142
L-lactate dehydrogenase A chain EC50 = 8.9 nM 8.05 Inhibition of recombinant human full-length N-terminal His-tagged LDHA (1 to 332... 31129449
A549 IC50 = 360.0 nM 6.44 Antiproliferative activity against human A549 cells assessed as reduction in cel... 31129449
L-lactate dehydrogenase A chain IC50 = 424.0 nM 6.37 Inhibition of human liver LDHA using sodium pyruvate as substrate after 5 mins i... 29120638
L-lactate dehydrogenase A chain IC50 = 424.0 nM 6.37 Inhibition of human liver LDHA using sodium pyruvate as substrate after 5 mins i... 29120638
L-lactate dehydrogenase B chain IC50 = 441.0 nM 6.36 Inhibition of human erythrocytes LDHB using sodium pyruvate as substrate after 5... 29120638
MIA PaCa-2 IC50 = 480.0 nM 6.32 Antiproliferative activity against human MIAPaCa2 cells assessed as reduction in... 31129449
MG-63 IC50 = 660.0 nM 6.18 Antiproliferative activity against human MG63 cells after 72 hrs by MTT assay 29861142
L-lactate dehydrogenase A chain IC50 = 670.0 nM 6.17 Inhibition of LDHA in human MiPaca2 cells assessed as inhibition of lactate prod... 27774125
L-lactate dehydrogenase IC50 = 877.0 nM 6.06 Inhibition of LDH in human MIAPaCa2 cells assessed as reduction in lactate produ... 29120638
MIA PaCa-2 IC50 = 1240.0 nM 5.91 Cytotoxicity against human MIAPaCa2 cells after 48 hrs by CellTiter-Glo assay 29120638
L-lactate dehydrogenase A chain EC50 = 1260.0 nM 5.9 Stabilization of LDHA in human A673 cell lysate preincubated for 20 mins followe... 29120638
L-lactate dehydrogenase IC50 = 1440.0 nM 5.84 Inhibition of LDH in human A673 cells assessed as reduction in lactate productio... 29120638
A673 IC50 = 2630.0 nM 5.58 Cytotoxicity against human A673 cells after 48 hrs by CellTiter-Glo assay 29120638

Literature References

PubMed DOI Target Context # Activities
27774125 10.1021/acsmedchemlett.6b00190 ADMET 17
29120638 10.1021/acs.jmedchem.7b00941 L-lactate dehydrogenase A chain 6
29120638 10.1021/acs.jmedchem.7b00941 L-lactate dehydrogenase 5
33765386 10.1021/acs.jmedchem.0c01898 L-lactate dehydrogenase A chain 3
31129449 10.1016/j.ejmech.2019.05.033 L-lactate dehydrogenase A chain 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
27774125 10.1021/acsmedchemlett.6b00190 L-lactate dehydrogenase A chain 2
31129449 10.1016/j.ejmech.2019.05.033 A549 2
31129449 10.1016/j.ejmech.2019.05.033 MIA PaCa-2 2
29861142 10.1016/j.bmcl.2018.05.052 L-lactate dehydrogenase A chain 2
29120638 10.1021/acs.jmedchem.7b00941 ADMET 2
29861142 10.1016/j.bmcl.2018.05.052 MG-63 1
29120638 10.1021/acs.jmedchem.7b00941 MIA PaCa-2 1
31129449 10.1016/j.ejmech.2019.05.033 MCF7 1
29120638 10.1021/acs.jmedchem.7b00941 A673 1
27774125 10.1021/acsmedchemlett.6b00190 L-lactate dehydrogenase B chain 1
27774125 10.1021/acsmedchemlett.6b00190 No relevant target 1
29120638 10.1021/acs.jmedchem.7b00941 Isocitrate dehydrogenase [NADP] cytoplasmic 1
31345633 10.1016/j.bmcl.2019.07.029 A549 1
29120638 10.1021/acs.jmedchem.7b00941 L-lactate dehydrogenase B chain 1

Data from ChEMBL 36 via Core Engine