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Compound Detail

CHEMBL207881

GW9508
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O=C(O)CCc1ccc(NCc2cccc(Oc3ccccc3)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL207881
Name GW9508
Phase Preclinical
Structure Type MOL
InChI Key DGENZVKCTGIDRZ-UHFFFAOYSA-N
5
Targets
30
Activities
2
Assay Types
6
PK Parameters
20
Publications
0
Known Names

Molecular Properties

347.4
MW (Da)
5.11
ALogP
3
HBA
2
HBD
58.6
PSA (Ų)
0.59
QED
1
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H21NO3
MW 347.41
Aromatic Rings 3
Heavy Atoms 26
NP-Likeness -0.60

Activity Summary

EC50 28 meas. best 7.89
Ki 2 meas. best 6.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Free fatty acid receptor 1
CHEMBL4422
 EC50 7.89 6.9005 13.0 22
GPR40-Galpha16
CHEMBL5482994
 EC50 7.32 7.32 48.0 1
Free fatty acid receptor 1
CHEMBL1795180
 EC50 7.0 7.0 99.0 1
Free fatty acid receptor 1
CHEMBL4422
 Ki 6.66 6.66 218.8 1
Prostaglandin E2 receptor EP3 subtype
CHEMBL3710
 Ki 6.4 6.4 398.1 1
Free fatty acid receptor 4
CHEMBL5339
 EC50 5.85 5.5675 1412.5 4

Pharmacokinetic Data

Parameter Value Units Species
CL 24.9 mL.min-1.kg-1 Rattus norvegicus
CL 0.74 mL.min-1.g-1 Homo sapiens
CL 2.3 mL.min-1.g-1 Rattus norvegicus
F 65.0 % Rattus norvegicus
T1/2 5.9 hr Rattus norvegicus
T1/2 5.3 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at human GPR40 expressed in CHO cells by calcium flux assay 24835985
Free fatty acid receptor 1 EC50 = 28.18 nM 7.55 Agonist activity at FFAR1 expressed in HEK 293 cells assessed as beta-arrestin r... 22519963
Free fatty acid receptor 1 EC50 = 28.18 nM 7.55 Agonist activity at human C-terminal eYFP-tagged FFA1 receptor expressed in HEK-... 27074625
Free fatty acid receptor 1 EC50 = 28.84 nM 7.54 Agonist activity at human FFA1 transfected in 1321N1 cells assessed as calcium m... 24900217
Free fatty acid receptor 1 EC50 = 47.86 nM 7.32 Agonist activity at human FFA1 expressed in CHO cells by Gal4 luciferase reporte... 18947221
Free fatty acid receptor 1 EC50 = 47.86 nM 7.32 Agonist activity at human FFA1 receptor expressed in human 1321N1 cells assessed... 21854074
Free fatty acid receptor 1 EC50 = 48.0 nM 7.32 Agonist activity at human GPR40 expressed in HEK293 cells assessed as increase i... 29980358
Free fatty acid receptor 1 EC50 = 48.0 nM 7.32 Agonist activity at GPR40 (unknown origin) 33843223
GPR40-Galpha16 EC50 = 48.0 nM 7.32 Agonist activity at human GPR40/Galpha-16 expressed in HEK293 cells by Fluo4-AM ... 38039791
Free fatty acid receptor 1 EC50 = 50.0 nM 7.3 Agonist activity at human GPR40 expressed in CHO cells after 24 hrs by NFAT-luci... 29259758
Free fatty acid receptor 1 EC50 = 50.12 nM 7.3 Agonist activity at human FFA1 expressed in HEK293 cells assessed as stimulation... 33127539
Free fatty acid receptor 1 EC50 = 50.0 nM 7.3 Agonist activity at GPR40 (unknown origin) expressed in CHO cells co-expressing ... 33769827
Free fatty acid receptor 1 EC50 = 64.57 nM 7.19 Agonist potency at human GPR40 expressed in CHO cells 16439116
Free fatty acid receptor 1 EC50 = 79.43 nM 7.1 Agonist activity at GPR40 receptor 17240142
Free fatty acid receptor 1 EC50 = 80.0 nM 7.1 Agonist activity at human GPR40 stably expressed in CHO cells assessed as increa... 38039791
Free fatty acid receptor 1 EC50 = 87.1 nM 7.06 Agonist activity at human FFA1 transfected in 1321N1 cells under serum-free cond... 24900217
Free fatty acid receptor 1 EC50 = 100.0 nM 7.0 Agonist activity at human GPR40 by FLIPR assay in presence of 1% BSA 20064714
Free fatty acid receptor 1 EC50 = 99.0 nM 7.0 Agonist activity at rat GPR40 expressed in CHO cells by calcium flux assay 24835985
Free fatty acid receptor 1 Ki = 218.78 nM 6.66 Displacement of 3-(2-Fluoro-4-((2'-methyl-4'-(2-(2-((7-nitrobenzo[c][1,2,5]-oxad... 27074625
Free fatty acid receptor 1 EC50 = 223.87 nM 6.65 Agonist activity at human GPR40 expressed in HEK-EM 293 cells assessed as increa... 17552505

Literature References

PubMed DOI Target Context # Activities
17552505 10.1021/jm0614782 Free fatty acid receptor 1 11
17240142 10.1016/j.bmcl.2006.12.084 Rattus norvegicus 5
- 10.6019/CHEMBL5058564 U2OS 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
27074625 10.1021/acs.jmedchem.6b00202 Free fatty acid receptor 1 3
24900217 10.1021/ml100106c Free fatty acid receptor 1 3
- 10.6019/CHEMBL5058564 Fibroblast 3
24835985 10.1016/j.bmcl.2014.04.065 Free fatty acid receptor 1 2
16439116 10.1016/j.bmcl.2006.01.007 Free fatty acid receptor 1 2
17240142 10.1016/j.bmcl.2006.12.084 Unchecked 2
17240142 10.1016/j.bmcl.2006.12.084 Liver microsomes 2
17240142 10.1016/j.bmcl.2006.12.084 No relevant target 2
23726411 10.1016/j.bmc.2013.05.013 Bone marrow cell 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
- 10.6019/CHEMBL5058564 HEK-293T 2
22519963 10.1021/jm300215x Free fatty acid receptor 4 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
22519963 10.1021/jm300215x Free fatty acid receptor 1 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
17240142 10.1016/j.bmcl.2006.12.084 Free fatty acid receptor 1 2

Data from ChEMBL 36 via Core Engine