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Compound Detail

CHEMBL2152070

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COc1ccc(F)c(-c2ccc(COc3cccc([C@@H](CC(=O)O)C4CC4)c3)cc2C2=CCCC2(C)C)c1

Basic Information

ChEMBL ID CHEMBL2152070
Phase Preclinical
Structure Type MOL
InChI Key CHEANNSDVJOIBS-MHZLTWQESA-N
2
Targets
15
Activities
2
Assay Types
30
PK Parameters
20
Publications
0
Known Names

Molecular Properties

514.6
MW (Da)
8.25
ALogP
3
HBA
1
HBD
55.8
PSA (Ų)
0.30
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C33H35FO4
MW 514.64
Aromatic Rings 3
Heavy Atoms 38
NP-Likeness 0.16

Activity Summary

EC50 14 meas. best 8.46
Kd 1 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Free fatty acid receptor 1
CHEMBL4422
EC50 8.46 6.9162 3.5 13
Free fatty acid receptor 1
CHEMBL4422
Kd 8.3 8.3 5.0 1
Free fatty acid receptor 1
CHEMBL1795180
EC50 7.94 7.94 11.4 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 7771.06 ng.hr.mL-1 Rattus norvegicus
AUC 9675.23 ng.hr.mL-1 Macaca fascicularis
CL 3.0 mL.min-1.kg-1 Mus musculus
CL 15.17 mL.min-1.kg-1 Rattus norvegicus
CL 13.5 mL.min-1.kg-1 Macaca fascicularis
CL 13.5 mL.min-1.kg-1 Macaca fascicularis
CL 15.17 mL.min-1.kg-1 Rattus norvegicus
CL 15.17 mL.min-1.kg-1 Rattus norvegicus
CL 15.17 mL.min-1.kg-1 Rattus norvegicus
CL 13.5 mL.min-1.kg-1 Macaca fascicularis
Cmax 14000.0 nM Mus musculus
Cmax 3600.0 nM Rattus norvegicus
Cmax 5100.0 nM Macaca fascicularis
F 100.0 % Mus musculus
F 72.0 % Rattus norvegicus
F 71.0 % Macaca fascicularis
F 71.0 % Macaca fascicularis
F 15.0 % Rattus norvegicus
F 15.0 % Rattus norvegicus
F 72.0 % Rattus norvegicus
F 71.0 % Macaca fascicularis
Fu 0.01 - Rattus norvegicus
Fu 0.012 - Macaca fascicularis
T1/2 2.0 hr Mus musculus
T1/2 1.8 hr Rattus norvegicus
T1/2 2.1 hr Macaca fascicularis
T1/2 2.1 hr Macaca fascicularis
T1/2 1.8 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 1.8 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 = 3.5 nM 8.46 Agonist activity at human GPR40 transfected in HEK293 cells assessed as increase... 29366647
Free fatty acid receptor 1 Kd = 5.0 nM 8.3 Binding affinity to human GPR40 expressed in CHO cells by LC-MS analysis 32900194
Free fatty acid receptor 1 EC50 = 11.4 nM 7.94 Agonist activity at rat GPR40 transfected in HEK293 cells assessed as increase i... 29366647
Free fatty acid receptor 1 EC50 = 13.0 nM 7.89 Agonist activity at GPR40 (unknown origin) expressed in mouse A9 cells assessed ... 24900845
Free fatty acid receptor 1 EC50 = 130.0 nM 6.89 Positive allosteric modulation of human GPR40 expressed in HEK293 cells assessed... 28197316
Free fatty acid receptor 1 EC50 = 130.0 nM 6.89 Positive allosteric modulation of recombinant human GPR40 expressed in HEK293 ce... 31109791
Free fatty acid receptor 1 EC50 = 150.0 nM 6.82 Agonist activity at human GPR40 expressed in CHO cells incubated for 60 mins by ... 32900194
Free fatty acid receptor 1 EC50 = 160.0 nM 6.8 Agonist activity at GPR40 expressed in CHO cells after 20 seconds by aequorin bi... 24900539
Free fatty acid receptor 1 EC50 = 160.0 nM 6.8 Agonist activity at human FFA1 receptor expressed in CHO cell membranes after 4 ... 24900707
Free fatty acid receptor 1 EC50 = 160.0 nM 6.8 Agonist activity at GPR40 (unknown origin) expressed in CHO cells incubated for ... 30034614
Free fatty acid receptor 1 EC50 = 160.0 nM 6.8 Agonist activity at GPR40 (unknown origin) expressed in CHO cells co-expressing ... 33769827
Free fatty acid receptor 1 EC50 = 161.0 nM 6.79 Agonist activity at GPR40 (unknown origin) expressed in CHO cells assessed as lu... 24900845
Free fatty acid receptor 1 EC50 = 392.0 nM 6.41 Positive allosteric modulation of human GPR40 expressed in HEK293 cells assessed... 28197316
Free fatty acid receptor 1 EC50 = 392.0 nM 6.41 Positive allosteric modulation of recombinant human GPR40 expressed in HEK293 ce... 31109791
Free fatty acid receptor 1 EC50 = 710.0 nM 6.15 Agonist activity at GPR40 expressed in CHO cells after 20 seconds by aequorin bi... 24900539

Literature References

PubMed DOI Target Context # Activities
24900539 10.1021/ml300133f Mus musculus 9
28197316 10.1021/acsmedchemlett.6b00443 Free fatty acid receptor 1 6
31109791 10.1016/j.bmcl.2019.04.050 Free fatty acid receptor 1 6
24900539 10.1021/ml300133f Rattus norvegicus 5
24900539 10.1021/ml300133f Cynomolgus monkey 5
30034614 10.1021/acsmedchemlett.8b00213 Rattus norvegicus 5
30034614 10.1021/acsmedchemlett.8b00213 Cynomolgus monkey 5
29366647 10.1016/j.bmcl.2018.01.013 Free fatty acid receptor 1 4
24900707 10.1021/ml300427u Rattus norvegicus 4
24900707 10.1021/ml300427u Cynomolgus monkey 4
32900194 10.1021/acs.jmedchem.0c00843 Free fatty acid receptor 1 3
24900845 10.1021/ml4005123 Rattus norvegicus 3
24900539 10.1021/ml300133f Free fatty acid receptor 1 2
24900707 10.1021/ml300427u Free fatty acid receptor 1 2
30034614 10.1021/acsmedchemlett.8b00213 ADMET 2
24900845 10.1021/ml4005123 Free fatty acid receptor 1 2
30034614 10.1021/acsmedchemlett.8b00213 Free fatty acid receptor 1 2
30655940 10.1021/acsmedchemlett.8b00444 Free fatty acid receptor 1 2
28197316 10.1021/acsmedchemlett.6b00443 Mus musculus 2
29258772 10.1016/j.bmcl.2017.12.022 Free fatty acid receptor 1 2

Data from ChEMBL 36 via Core Engine