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Compound Detail

CHEMBL384073

GSK-180736A
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CC1=C(C(=O)Nc2ccc3[nH]ncc3c2)C(c2ccc(F)cc2)NC(=O)N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL384073
Name GSK-180736A
Phase Preclinical
Structure Type MOL
InChI Key HEAIGWIZTYAQTC-UHFFFAOYSA-N
10
Targets
22
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

365.4
MW (Da)
2.97
ALogP
3
HBA
4
HBD
98.9
PSA (Ų)
0.57
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H16FN5O2
MW 365.37
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.94

Activity Summary

IC50 22 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Rho-associated protein kinase 1
CHEMBL3231
 IC50 7.85 7.4525 14.0 4
Beta-adrenergic receptor kinase 1
CHEMBL3711550
 IC50 6.6 6.355 250.0 2
Beta-adrenergic receptor kinase 1
CHEMBL4079
 IC50 6.41 6.16 390.0 6
Thoracic aorta
CHEMBL2367449
 IC50 6.12 6.12 760.0 1
Aorta
CHEMBL613606
 IC50 6.12 6.12 760.0 1
Ribosomal protein S6 kinase beta-1
CHEMBL4501
 IC50 5.54 5.54 2850.0 2
Ribosomal protein S6 kinase alpha-1
CHEMBL2553
 IC50 5.51 5.51 3100.0 2
Unchecked
CHEMBL612545
 IC50 4.52 4.52 30000.0 2
G protein-coupled receptor kinase 5
CHEMBL3879830
 IC50 4.0 4.0 100000.0 1
G protein-coupled receptor kinase 5
CHEMBL5678
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 49.0 mL.min-1.kg-1 Rattus norvegicus
CL 50.0 mL.min-1.kg-1 Rattus norvegicus
CL 49.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1551.85 nM Rattus norvegicus
F - % Rattus norvegicus
T1/2 0.7 hr Rattus norvegicus
T1/2 0.7 hr Rattus norvegicus
T1/2 0.3433 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Rho-associated protein kinase 1 IC50 = 14.0 nM 7.85 Inhibition of human recombinant ROCK1 kinase expressed in insect Sf9 cells by SP... 18842034
Rho-associated protein kinase 1 IC50 = 14.0 nM 7.85 Inhibition of human recombinant ROCK1 expressed in Sf9 cells at 10 mM 17201405
Rho-associated protein kinase 1 IC50 = 78.0 nM 7.11 Assays for Inhibition of ROCK: Rho-associated coiled-coil kinase (ROCK) assays w... -
Rho-associated protein kinase 1 IC50 = 100.0 nM 7.0 Inhibition of ROCK1 (unknown origin) by ADP-Glo kinase assay 27050625
Beta-adrenergic receptor kinase 1 IC50 = 250.0 nM 6.6 Inhibition of bovine GRK2 S670A mutant assessed as decrease in phosphorylation o... 27362616
Beta-adrenergic receptor kinase 1 IC50 = 390.0 nM 6.41 Inhibition of GRK2 (unknown origin) using CRRREEEEESAAA as substrate measured fo... 36055000
Thoracic aorta IC50 = 760.0 nM 6.12 Dilatory activity against phenylephrine-induced contraction of Sprague-Dawley ra... 17201405
Aorta IC50 = 760.0 nM 6.12 Inhibition of phenylephrine-induced aortic ring contraction in Sprague-Dawley ra... 18842034
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Inhibition of GRK2 (unknown origin) 33481605
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Assays for Inhibition of GRKs: GRK1, 2 and 5 kinetic assays were conducted in a ... -
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Inhibition of GRK2 (unknown origin) 36055000
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Inhibition of bovine GRK2 S670A mutant after 5 mins in presence of ATP by phosph... 28323425
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Inhibition of GRK2 (unknown origin) 28323425
Beta-adrenergic receptor kinase 1 IC50 = 770.0 nM 6.11 Inhibition of full length C-terminal hexahistidine tagged GRK2 (unknown origin) ... 27050625
Ribosomal protein S6 kinase beta-1 IC50 = 2850.0 nM 5.54 Inhibition of p70S6K 17201405
Ribosomal protein S6 kinase beta-1 IC50 = 2850.0 nM 5.54 Inhibition of p70S6K 18842034
Ribosomal protein S6 kinase alpha-1 IC50 = 3100.0 nM 5.51 Inhibition of RSK1 17201405
Ribosomal protein S6 kinase alpha-1 IC50 = 3100.0 nM 5.51 Inhibition of RSK1 18842034
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of PKA (unknown origin) using CREBtide as substrate by ADP-Glo kinase... 27050625
Unchecked IC50 = 30000.0 nM 4.52 Inhibition of mouse PKA using CREBtide as substrate after 30 mins in presence of... 28323425

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL1961873 Tyrosine-protein kinase ABL1 14
- 10.6019/CHEMBL1961873 Epidermal growth factor receptor 10
- 10.6019/CHEMBL1961873 Platelet-derived growth factor receptor alpha 8
- 10.6019/CHEMBL1961873 Mast/stem cell growth factor receptor Kit 8
17201405 10.1021/jm0609014 Rattus norvegicus 6
- 10.6019/CHEMBL1961873 Proto-oncogene tyrosine-protein kinase receptor Ret 6
- 10.6019/CHEMBL1961873 Leucine-rich repeat serine/threonine-protein kinase 2 4
- 10.6019/CHEMBL1961873 Cyclin-dependent kinase 2 4
- 10.6019/CHEMBL1961873 Protein kinase C beta type 4
- 10.6019/CHEMBL1961873 Tyrosine-protein kinase Lyn 4
- 10.6019/CHEMBL1961873 Serine/threonine-protein kinase B-raf 4
- 10.6019/CHEMBL1961873 Receptor-type tyrosine-protein kinase FLT3 4
18842034 10.1021/jm8005096 Rattus norvegicus 3
27362616 10.1021/acs.jmedchem.5b01939 Unchecked 3
28323425 10.1021/acs.jmedchem.7b00112 Beta-adrenergic receptor kinase 1 3
- 10.6019/CHEMBL1961873 G protein-coupled receptor kinase 6 2
- 10.6019/CHEMBL1961873 RAC-gamma serine/threonine-protein kinase 2
- 10.6019/CHEMBL1961873 RAC-beta serine/threonine-protein kinase 2
- 10.6019/CHEMBL1961873 RAC-alpha serine/threonine-protein kinase 2
36055000 10.1016/j.ejmech.2022.114668 Beta-adrenergic receptor kinase 1 2

Data from ChEMBL 36 via Core Engine