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Compound Detail

CHEMBL449588

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Cc1ccccc1C#Cc1ccc(CCC(=O)O)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL449588
Phase Preclinical
Structure Type MOL
InChI Key FODHWOBAQBTTFS-UHFFFAOYSA-N
9
Targets
16
Activities
3
Assay Types
11
PK Parameters
20
Publications
0
Known Names

Molecular Properties

264.3
MW (Da)
3.41
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.86
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H16O2
MW 264.32
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.36

Activity Summary

EC50 8 meas. best 7.5
IC50 7 meas. best 6.6
Ki 1 meas. best 6.2

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Free fatty acid receptor 1
CHEMBL4422
 EC50 7.5 7.3633 32.0 6
Sphingosine 1-phosphate receptor 1
CHEMBL4333
 IC50 6.6 6.6 248.9 1
Apelin receptor
CHEMBL1628481
 IC50 6.49 6.49 324.9 1
Psychosine receptor
CHEMBL3714081
 IC50 6.44 6.44 364.8 1
G-protein coupled receptor 183
CHEMBL3259470
 IC50 6.24 6.24 582.5 1
Muscarinic acetylcholine receptor M2
CHEMBL211
 IC50 6.22 6.22 602.2 1
Free fatty acid receptor 1
CHEMBL4422
 Ki 6.2 6.2 631.0 1
fMet-Leu-Phe receptor
CHEMBL3359
 IC50 5.89 5.89 1279.2 1
Free fatty acid receptor 4
CHEMBL5339
 EC50 5.84 5.745 1445.4 2
N-formyl peptide receptor 3
CHEMBL5646
 IC50 5.84 5.84 1428.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 3416.67 ng.hr.mL-1 Mus musculus
AUC 783.33 ng.hr.mL-1 Mus musculus
CL 53.0 mL.min-1.kg-1 Mus musculus
Cmax 9802.51 nM Mus musculus
Cmax 8641.04 nM Mus musculus
F 109.0 % Mus musculus
T1/2 0.8 hr Mus musculus
T1/2 0.1667 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.08333 hr Mus musculus
Vd 0.8 L.kg-1 Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Free fatty acid receptor 1 EC50 = 32.0 nM 7.5 Agonist activity at human FFA1 expressed in human 1321N1 cells by calcium fluore... 18947221
Free fatty acid receptor 1 EC50 = 32.36 nM 7.49 Agonist activity at human FFA1 expressed in human 1321N1 cells by calcium fluore... 18947221
Free fatty acid receptor 1 EC50 = 45.71 nM 7.34 Agonist activity at human FFA1 receptor expressed in human 1321N1 cells assessed... 21854074
Free fatty acid receptor 1 EC50 = 46.0 nM 7.34 Agonist activity at human FFA1 assessed as calcium mobilization measured for 50 ... 23294321
Free fatty acid receptor 1 EC50 = 45.71 nM 7.34 Agonist activity at human FFA1 receptor transfected in human 1321N1 cells by cal... 23687558
Free fatty acid receptor 1 EC50 = 67.61 nM 7.17 Agonist activity at human C-terminal eYFP-tagged FFA1 receptor expressed in HEK-... 27074625
Sphingosine 1-phosphate receptor 1 IC50 = 248.92 nM 6.6 GPCR PRESTO-Tango dose-response in antagonist mode with target: S1PR1 -
Apelin receptor IC50 = 324.85 nM 6.49 GPCR PRESTO-Tango dose-response in antagonist mode with target: APLNR -
Psychosine receptor IC50 = 364.84 nM 6.44 GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR65 -
G-protein coupled receptor 183 IC50 = 582.5 nM 6.24 GPCR PRESTO-Tango dose-response in antagonist mode with target: GPR183 -
Muscarinic acetylcholine receptor M2 IC50 = 602.2 nM 6.22 GPCR PRESTO-Tango dose-response in antagonist mode with target: CHRM2 -
Free fatty acid receptor 1 Ki = 630.96 nM 6.2 Displacement of 3-(2-Fluoro-4-((2'-methyl-4'-(2-(2-((7-nitrobenzo[c][1,2,5]-oxad... 27074625
fMet-Leu-Phe receptor IC50 = 1279.16 nM 5.89 GPCR PRESTO-Tango dose-response in antagonist mode with target: FPR1 -
Free fatty acid receptor 4 EC50 = 1445.44 nM 5.84 Agonist activity at C-terminal yellow fluorescent protein-fused human FFA4 recep... 23687558
N-formyl peptide receptor 3 IC50 = 1427.99 nM 5.84 GPCR PRESTO-Tango dose-response in antagonist mode with target: FPR3 -
Free fatty acid receptor 4 EC50 = 2238.72 nM 5.65 Agonist activity at GPR120 expressed in HEK 293 cells assessed as beta-arrestin ... 22519963

Literature References

PubMed DOI Target Context # Activities
23294321 10.1021/jm301470a Mus musculus 13
- 10.6019/CHEMBL5058564 HEK-293T 9
18947221 10.1021/jm8010178 Unchecked 7
- 10.6019/CHEMBL5058564 U2OS 7
- 10.6019/CHEMBL5058564 Fibroblast 6
21854074 10.1021/jm2005699 No relevant target 4
18947221 10.1021/jm8010178 Free fatty acid receptor 1 4
23294321 10.1021/jm301470a ADMET 3
23294321 10.1021/jm301470a No relevant target 3
27074625 10.1021/acs.jmedchem.6b00202 Free fatty acid receptor 1 3
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
23687558 10.1021/ml4000673 Free fatty acid receptor 4 2
23687558 10.1021/ml4000673 Free fatty acid receptor 1 2
22519963 10.1021/jm300215x Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 G-protein coupled receptor 35 2
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 2
21854074 10.1021/jm2005699 Free fatty acid receptor 1 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine