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Compound Detail

CHEMBL1829173

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CC#C[C@@H](CC(=O)O)c1ccc(OCc2cccc(-c3ccc(C(F)(F)F)cc3)c2)cc1

Basic Information

ChEMBL ID CHEMBL1829173
Phase Preclinical
Structure Type MOL
InChI Key ZOPNBMMVVZRSGH-NRFANRHFSA-N
5
Targets
28
Activities
4
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

438.4
MW (Da)
6.53
ALogP
2
HBA
1
HBD
46.5
PSA (Ų)
0.43
QED
1
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C26H21F3O3
MW 438.45
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.34

Activity Summary

EC50 24 meas. best 8.89
Ki 2 meas. best 8.66
IC50 1 meas. best 5.52
Kd 1 meas. best 8.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Free fatty acid receptor 1
CHEMBL4422
EC50 8.89 7.4721 1.3 19
Free fatty acid receptor 1
CHEMBL5411
EC50 8.82 8.355 1.5 2
Free fatty acid receptor 1
CHEMBL4422
Kd 8.72 8.72 1.9 1
Free fatty acid receptor 1
CHEMBL4422
Ki 8.66 8.02 2.2 2
Free fatty acid receptor 1
CHEMBL1795180
EC50 8.49 8.065 3.2 2
MIN6
CHEMBL4483258
EC50 8.32 8.32 4.8 1
Unchecked
CHEMBL612545
IC50 5.52 5.52 3000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 47500.0 ng.hr.mL-1 Mus musculus
AUC 6160.0 ng.hr.mL-1 Rattus norvegicus
AUC 33800.0 ng.hr.mL-1 Canis lupus familiaris
AUC 7370.0 ng.hr.mL-1 Macaca fascicularis
AUC 33859.0 ng.hr.mL-1 Mus musculus
CL 1.167 mL.min-1.kg-1 Mus musculus
CL 1.167 mL.min-1.kg-1 Rattus norvegicus
CL 1.333 mL.min-1.kg-1 Canis lupus familiaris
CL 1.0 mL.min-1.kg-1 Macaca fascicularis
CL 1.167 mL.min-1.kg-1 Rattus norvegicus
CL 15.49 uL.min-1.(10^6cells)-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Macaca mulatta
CL 1.0 mL.min-1.kg-1 Canis lupus familiaris
CL 1.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.0 mL.min-1.kg-1 Mus musculus
Cmax 17000.0 nM Mus musculus
Cmax 1400.0 nM Rattus norvegicus
Cmax 7500.0 nM Canis lupus familiaris
Cmax 2100.0 nM Macaca fascicularis
F 67.0 % Mus musculus
F 84.0 % Rattus norvegicus
F 100.0 % Canis lupus familiaris
F 88.0 % Macaca fascicularis
F 84.0 % Rattus norvegicus
F 67.0 % Macaca mulatta
F 67.0 % Canis lupus familiaris
F 67.0 % Rattus norvegicus
F 67.0 % Mus musculus
MRT 10.0 hr Rattus norvegicus
T1/2 8.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Free fatty acid receptor 1 EC50 = 1.3 nM 8.89 Agonist activity at human recombinant full length GPR40 overexpressed in human H... 27749056
Free fatty acid receptor 1 EC50 = 1.5 nM 8.82 Agonist activity at Prolink-tagged mouse GPR40 fused with EA-tagged beta-arresti... 27749056
Free fatty acid receptor 1 Kd = 1.9 nM 8.72 Displacement of [3H]-(S)-2-(6-((2',6'-dimethyl-4'-(3-(methylsulfonyl)propoxy)bip... 27749056
Free fatty acid receptor 1 EC50 = 2.2 nM 8.66 Agonist activity at human GPR40 expressed in HEK293 cells measured after 18 to 2... 27994752
Free fatty acid receptor 1 Ki = 2.2 nM 8.66 Displacement of [3H]-TAK-875 from human recombinant full-length GPR40 expressed ... 27749056
Free fatty acid receptor 1 EC50 = 3.2 nM 8.49 Agonist activity at Prolink-tagged rat GPR40 fused with EA-tagged beta-arrestin ... 27749056
MIN6 EC50 = 4.8 nM 8.32 Induction of insulin secretion in mouse MIN6 cells 22217876
Free fatty acid receptor 1 EC50 = 11.0 nM 7.96 Agonist activity at human recombinant full-length Prolink-tagged GPR40 fused wit... 27749056
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at mouse GPR40 22217876
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Partial agonist activity at human GPR40 expressed in CHO cells measured over 20 ... 26620255
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at GPR40 (unknown origin) by calcium flux assay 27825762
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at FFA1 (unknown origin) 30296685
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at FFA1 (unknown origin) 36343410
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at human GPR40 expressed in HEK293 cells by Fluo4-AM dye based ... 38039791
Free fatty acid receptor 1 EC50 = 15.0 nM 7.82 Agonist activity at human recombinant full length GPR40 overexpressed in human H... 27749056
Free fatty acid receptor 1 EC50 = 23.0 nM 7.64 Agonist activity at FFA1 receptor (unknown origin) 27647366
Free fatty acid receptor 1 EC50 = 23.0 nM 7.64 Agonist activity at rat GPR40 22217876
Free fatty acid receptor 1 EC50 = 41.0 nM 7.39 Agonist activity at human GPR40 expressed in mouse A9 cells by inositol phosphat... 24900872
Free fatty acid receptor 1 Ki = 41.69 nM 7.38 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 = 60.0 nM 7.22 Agonist activity at GPR40 expressed in CHO cells after 20 seconds by aequorin bi... 24900539

Literature References

PubMed DOI Target Context # Activities
27749056 10.1021/acs.jmedchem.6b00892 Free fatty acid receptor 1 15
27825762 10.1016/j.bmcl.2016.10.074 ADMET 12
22217876 10.1016/j.bmcl.2011.10.118 Mus musculus 9
- 10.6019/CHEMBL5058564 Fibroblast 6
22217876 10.1016/j.bmcl.2011.10.118 Rattus norvegicus 6
22217876 10.1016/j.bmcl.2011.10.118 Canis familiaris 6
22217876 10.1016/j.bmcl.2011.10.118 Cynomolgus monkey 6
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL5058564 U2OS 5
27074625 10.1021/acs.jmedchem.6b00202 Free fatty acid receptor 1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5058564 HEK-293T 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
27749056 10.1021/acs.jmedchem.6b00892 ADMET 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5

Data from ChEMBL 36 via Core Engine