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Compound Detail

CHEMBL1783734

PIRAGLIATIN
🧪 Phase II
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🧪 Phase II
CS(=O)(=O)c1ccc([C@@H](C[C@H]2CCC(=O)C2)C(=O)Nc2cnccn2)cc1Cl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1783734
Name PIRAGLIATIN
Phase Phase II
Structure Type MOL
InChI Key XEANIURBPHCHMG-SWLSCSKDSA-N

Known Names

Piragliatin Piragliatina Piragliatine R04389620 R04389620\ RO-4389620 RO-4389620-R1440 RO4389620-R1440
2
Targets
7
Activities
2
Assay Types
30
PK Parameters
20
Publications
8
Known Names

Molecular Properties

421.9
MW (Da)
3.02
ALogP
6
HBA
1
HBD
106.1
PSA (Ų)
0.77
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer
USAN Stem -gliatin
USAN Year 2007

Extended Properties

Molecular Formula C19H20ClN3O4S
MW 421.91
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.87

Activity Summary

EC50 5 meas. best 7.0
Kd 2 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Hexokinase-4
CHEMBL3882
 EC50 7.0 7.0 100.0 1
Hexokinase-4
CHEMBL3820
 Kd 6.66 6.37 218.4 2
Hexokinase-4
CHEMBL3820
 EC50 6.44 5.9825 364.0 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 1200.0 ng.hr.mL-1 Macaca mulatta
AUC 3416.0 ng.hr.mL-1 Macaca mulatta
AUC 38000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 8830.0 ng.hr.mL-1 Canis lupus familiaris
AUC 8253.0 ng.hr.mL-1 Rattus norvegicus
AUC 1885.0 ng.hr.mL-1 Rattus norvegicus
AUC 1622.0 ng.hr.mL-1 Rattus norvegicus
AUC 5804.0 ng.hr.mL-1 Mus musculus
AUC 1765.0 ng.hr.mL-1 Mus musculus
AUC 1501.0 ng.hr.mL-1 Mus musculus
AUC 574.0 ng.hr.mL-1 Mus musculus
AUC 2330.0 ng.hr.mL-1 Mus musculus
AUC 351.0 ng.hr.mL-1 Mus musculus
AUC 3230.0 ng.hr/g Mus musculus
AUC 15700.0 ng.hr/g Mus musculus
AUC 1470.0 ng.hr/g Mus musculus
AUC 1020.0 ng.hr/g Mus musculus
AUC 5030.0 ng.hr/g Mus musculus
AUC 505.0 ng.hr/g Mus musculus
CL 24.47 mL.min-1.kg-1 Macaca mulatta
CL 19.66 mL.min-1.kg-1 Canis lupus familiaris
CL 103.85 mL.min-1.kg-1 Rattus norvegicus
CL 111.26 mL.min-1.kg-1 Mus musculus
CL 2.2 mL.min-1.kg-1 Homo sapiens
Cmax 602.02 nM Macaca mulatta
Cmax 7887.94 nM Macaca mulatta
Cmax 12391.27 nM Canis lupus familiaris
Cmax 20739.02 nM Canis lupus familiaris
Cmax 5309.19 nM Rattus norvegicus
Cmax 957.55 nM Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Hexokinase-4 EC50 = 100.0 nM 7.0 Activation of rat glucokinase -
Hexokinase-4 Kd = 218.4 nM 6.66 Binding affinity to biotinylated human recombinant glucokinase expressed in Esch... -
Hexokinase-4 EC50 = 364.0 nM 6.44 Activation of recombinant human glucokinase assessed as formation of glucose-6-p... -
Hexokinase-4 EC50 = 364.0 nM 6.44 Activation of recombinant human glucokinase assessed as formation of glucose-6-p... -
Hexokinase-4 Kd = 830.0 nM 6.08 Displacement of TAFMT from human pancreatic N-terminal His6-tagged glucokinase i... 27391254
Hexokinase-4 EC50 = 1420.0 nM 5.85 Activation of human recombinant glucokinase using 6.5 mM glucose by spectrophoto... 19435665
Hexokinase-4 EC50 = 6320.0 nM 5.2 Activation of recombinant human glucokinase assessed as NADPH formation using gl... 26685731

Literature References

PubMed DOI Target Context # Activities
30006171 10.1016/j.ejmech.2018.06.060 ADMET 18
22809456 10.1021/jm3008689 Mus musculus 16
22809456 10.1021/jm3008689 Rattus norvegicus 13
22809456 10.1021/jm3008689 Liver microsomes 12
22809456 10.1021/jm3008689 ADMET 11
22809456 10.1021/jm3008689 Liver 10
22809456 10.1021/jm3008689 Canis familiaris 9
22809456 10.1021/jm3008689 Rhesus monkey 8
22809456 10.1021/jm3008689 Plasma 5
- 10.1039/C4MD00027G Hexokinase-4 5
27391254 10.1021/acs.jmedchem.6b00632 Hexokinase-4 5
22809456 10.1021/jm3008689 Hexokinase-4 4
30006171 10.1016/j.ejmech.2018.06.060 Mus musculus 3
26685731 10.1021/acs.jmedchem.5b01594 Hexokinase-4 2
19435665 10.1016/j.bmcl.2009.04.107 Hexokinase-4 2
- 10.1039/C4MD00027G Rattus norvegicus 2
- 10.6019/CHEMBL3301361 No relevant target 2
26685731 10.1021/acs.jmedchem.5b01594 Mus musculus 2
- 10.1039/C1MD00116G Hexokinase-4 2
22809456 10.1021/jm3008689 No relevant target 2

Data from ChEMBL 36 via Core Engine