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Compound Detail

CHEMBL2177757

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O=C(Cc1ccccc1)Nc1nnc(CCSCCc2nnc(NC(=O)Cc3ccccc3)s2)s1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2177757
Phase Preclinical
Structure Type MOL
InChI Key MDJIPXYRSZHCFS-UHFFFAOYSA-N
12
Targets
56
Activities
2
Assay Types
20
PK Parameters
20
Publications
0
Known Names

Molecular Properties

524.7
MW (Da)
4.27
ALogP
9
HBA
2
HBD
109.8
PSA (Ų)
0.27
QED
1
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H24N6O2S3
MW 524.70
Aromatic Rings 4
Heavy Atoms 35
NP-Likeness -1.29

Activity Summary

IC50 54 meas. best 7.6
Kd 2 meas. best 6.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutaminase kidney isoform, mitochondrial
CHEMBL2146302
 IC50 7.6 6.27 25.0 26
Unchecked
CHEMBL612545
 IC50 7.55 6.708 28.0 10
Glutaminase kidney isoform, mitochondrial
CHEMBL2146302
 Kd 6.7 6.035 200.0 2
A549
CHEMBL392
 IC50 6.56 5.75 276.0 3
HCT-116
CHEMBL394
 IC50 6.27 5.5075 540.0 4
CAKI-1
CHEMBL614067
 IC50 5.94 5.94 1160.0 1
MDA-MB-436
CHEMBL4296465
 IC50 5.62 5.455 2400.0 2
MDA-MB-231
CHEMBL400
 IC50 5.58 5.2633 2610.0 3
Glutaminase kidney isoform, mitochondrial
CHEMBL4523186
 IC50 5.48 5.48 3300.0 1
ASPC1
CHEMBL612588
 IC50 4.99 4.99 10200.0 1
SW1990
CHEMBL1075592
 IC50 4.45 4.45 35330.0 1
HCC827
CHEMBL4296422
 IC50 4.37 4.37 42400.0 1
HT-1080
CHEMBL614580
 IC50 4.32 4.32 47720.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 636.0 ng.hr.mL-1 Rattus norvegicus
AUC 73.0 ng.hr.mL-1 Rattus norvegicus
AUC 543.3 ng.hr.mL-1 Rattus norvegicus
AUC 12.5 ng.hr.mL-1 Rattus norvegicus
AUC 2092.3 ng.hr.mL-1 Rattus norvegicus
CL 20.42 mL.min-1.g-1 Homo sapiens
CL 53.0 mL.min-1.kg-1 Rattus norvegicus
CL 1883.33 mL.min-1.kg-1 Rattus norvegicus
CL 1475.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 76.23 nM Rattus norvegicus
Cmax 940.35 nM Rattus norvegicus
Cmax 33.92 nM Rattus norvegicus
F 2.0 % Rattus norvegicus
F 2.3 % Rattus norvegicus
T1/2 5.3 hr Rattus norvegicus
T1/2 2.0 hr Rattus norvegicus
T1/2 0.755 hr Homo sapiens
T1/2 3.8 hr Rattus norvegicus
T1/2 2.6 hr Rattus norvegicus
Tmax 0.7 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutaminase kidney isoform, mitochondrial IC50 = 25.0 nM 7.6 Inhibition of recombinant human GLS1 using glutamine as substrate preincubated f... 33118821
Unchecked IC50 = 28.0 nM 7.55 Inhibition of GLS in human PC3 cells using glutamine as substrate measured after... 31199640
Unchecked IC50 = 63.0 nM 7.2 Inhibition of recombinant human His-tagged KGA R387A mutant expressed in Escheri... 28609101
Unchecked IC50 = 65.0 nM 7.19 Inhibition of recombinant human His-tagged KGA S384A mutant expressed in Escheri... 28609101
Unchecked IC50 = 66.0 nM 7.18 Inhibition of recombinant human His-tagged KGA K507A mutant expressed in Escheri... 28609101
Glutaminase kidney isoform, mitochondrial IC50 = 81.0 nM 7.09 Inhibition of recombinant human His-tagged KGA (L123 to L669 residues) expressed... 28609101
Glutaminase kidney isoform, mitochondrial IC50 = 100.0 nM 7.0 Recombinant Enzyme Assay: Compounds were assessed for their ability to inhibit t... -
Unchecked IC50 = 100.0 nM 7.0 Recombinant Enzyme Assay - Time Dependence: Compounds were assessed for their ab... -
Glutaminase kidney isoform, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of human recombinant GAC (72 to 598 residues) expressed in Escherichi... 30543285
Glutaminase kidney isoform, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of GAC (unknown origin) assessed as NADH formation using 1.8 to 13 mM... 29969024
Glutaminase kidney isoform, mitochondrial IC50 = 100.0 nM 7.0 Inhibition of GAC (unknown origin) assessed as NADH formation using 10 mM glutam... 29969024
Glutaminase kidney isoform, mitochondrial IC50 = 100.0 nM 7.0 Enzyme Assay-Time Dependence: Compounds were assessed for their ability to inhib... -
Glutaminase kidney isoform, mitochondrial IC50 = 130.0 nM 6.89 Inhibition of human KGA preincubated for 15 to 30 mins followed by substrate add... 30543285
Glutaminase kidney isoform, mitochondrial IC50 = 135.0 nM 6.87 Inhibition of recombinant 6His-tagged GLS1 KGA isoform (unknown origin) (63 to 6... 31199640
Unchecked IC50 = 160.0 nM 6.8 Inhibition of KGA (unknown origin) using glutamine as substrate preincubated for... 30148361
Glutaminase kidney isoform, mitochondrial IC50 = 190.0 nM 6.72 Inhibition of human KGA (1 to 669 residues) preincubated for 20 mins using 7 mM ... 29969024
Glutaminase kidney isoform, mitochondrial IC50 = 190.0 nM 6.72 Inhibition of human kidney glutaminase assessed as reduction in glutamate produc... 33069080
Unchecked IC50 = 200.0 nM 6.7 Recombinant Enzyme Assay: Compounds were assessed for their ability to inhibit t... -
Glutaminase kidney isoform, mitochondrial IC50 = 200.0 nM 6.7 Enzyme Assay: Compounds were assessed for their ability to inhibit the enzymatic... -
Glutaminase kidney isoform, mitochondrial Kd = 200.0 nM 6.7 Binding affinity to recombinant human C-terminal His-tagged GLS1 after 3 hrs in ... 30148361

Literature References

PubMed DOI Target Context # Activities
36525694 10.1016/j.ejmech.2022.115014 ADMET 16
36055003 10.1016/j.ejmech.2022.114686 ADMET 13
28609101 10.1021/acs.jmedchem.7b00282 Rattus norvegicus 9
36055003 10.1016/j.ejmech.2022.114686 A549 9
28609101 10.1021/acs.jmedchem.7b00282 Unchecked 8
31603674 10.1021/acs.jmedchem.9b01035 Glutaminase kidney isoform, mitochondrial 6
28609101 10.1021/acs.jmedchem.7b00282 ASPC1 5
36055003 10.1016/j.ejmech.2022.114686 HCT-116 4
29969024 10.1021/acs.jmedchem.8b00327 Glutaminase kidney isoform, mitochondrial 4
30543285 10.1021/acs.jmedchem.8b01198 Glutaminase kidney isoform, mitochondrial 3
33792311 10.1021/acs.jmedchem.0c02044 Glutaminase kidney isoform, mitochondrial 3
30543285 10.1021/acs.jmedchem.8b01198 HCT-116 2
33069080 10.1016/j.bmc.2020.115698 Glutaminase kidney isoform, mitochondrial 2
30543285 10.1021/acs.jmedchem.8b01198 H22 2
33176943 10.1016/j.ejmech.2020.112980 MDA-MB-231 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33118821 10.1021/acs.jmedchem.0c01398 ADMET 2
30543285 10.1021/acs.jmedchem.8b01198 CAKI-1 2
29969024 10.1021/acs.jmedchem.8b00327 No relevant target 2
- 10.6019/CHEMBL3301361 ADMET 2

Data from ChEMBL 36 via Core Engine