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Compound Detail

CHEMBL281211

ARACHIDONYL TRIFLUOROMETHYLKETONE
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)C(F)(F)F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL281211
Name ARACHIDONYL TRIFLUOROMETHYLKETONE
Phase Preclinical
Structure Type MOL
InChI Key PLWROONZUDKYKG-DOFZRALJSA-N
11
Targets
18
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

356.5
MW (Da)
7.26
ALogP
1
HBA
0
HBD
17.1
PSA (Ų)
0.24
QED
1
Ro5 Violations
14
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H31F3O
MW 356.47
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 0.65

Activity Summary

IC50 17 meas. best 7.91
EC50 1 meas. best 4.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 7.91 7.1133 12.3 3
Cytosolic phospholipase A2 gamma
CHEMBL4834
 IC50 6.38 6.38 420.0 1
Cytosolic phospholipase A2 beta
CHEMBL4136
 IC50 6.1 6.1 800.0 1
Cytosolic phospholipase A2
CHEMBL3816
 IC50 5.64 5.64 2300.0 3
Unchecked
CHEMBL612545
 IC50 5.64 5.64 2300.0 1
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 5.43 5.43 3700.0 1
Monoglyceride lipase
CHEMBL4191
 IC50 5.2 5.195 6310.0 2
Cytosolic phospholipase A2
CHEMBL2304401
 IC50 4.96 4.96 11000.0 2
Cannabinoid receptor 1
CHEMBL3571
 EC50 4.6 4.6 25118.9 1
HL-60
CHEMBL383
 IC50 4.54 4.54 29000.0 1
THP-1
CHEMBL614245
 IC50 4.39 4.23 41000.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty-acid amide hydrolase 1 IC50 = 12.3 nM 7.91 Inhibition of human FAAH 19583260
Fatty-acid amide hydrolase 1 IC50 = 12.3 nM 7.91 Inhibition of human recombinant FAAH-maltose binding protein 19883085
Cytosolic phospholipase A2 gamma IC50 = 420.0 nM 6.38 Concentration required to inhibit human Cytosolic phospholipase A2 11229777
Cytosolic phospholipase A2 beta IC50 = 800.0 nM 6.1 Inhibitory activity against cytosolic Phospholipase A2 (PLA2) by soluble assay 11882004
Cytosolic phospholipase A2 IC50 = 2300.0 nM 5.64 Inhibition of human platelet cPLA2-alpha assessed as arachidonic acid release by... 17320401
Cytosolic phospholipase A2 IC50 = 2300.0 nM 5.64 Inhibition of human platelet cPLA2-alpha activity 18321717
Cytosolic phospholipase A2 IC50 = 2300.0 nM 5.64 Inhibition of cPLA2 from human platelets by RP-HPLC 20005725
Unchecked IC50 = 2300.0 nM 5.64 Inhibition of human platelet cytosolic phospholipase A2alpha 21316224
Fatty-acid amide hydrolase 1 IC50 = 3000.0 nM 5.52 Inhibition of fatty acid amide hydrolase; range =. 23-3 uM 16078824
Fatty-acid amide hydrolase 1 IC50 = 3700.0 nM 5.43 Inhibition of FAAH from rat brain microsomes by RP-HPLC 20005725
Monoglyceride lipase IC50 = 6310.0 nM 5.2 Inhibition of human MGL 19583260
Monoglyceride lipase IC50 = 6456.54 nM 5.19 Inhibition of human MGL activity using [3H]2-oleoylglycerol substrate by liquid ... 19883085
Cytosolic phospholipase A2 IC50 = 11000.0 nM 4.96 Inhibitory activity against cPLA2 (cytosolic Phospholipase A2) by measuring the ... 9276015
Cytosolic phospholipase A2 IC50 = 11000.0 nM 4.96 Inhibition of cPLA2 measuring Calcium ionophore A-23,187-induced arachidonic aci... 9341913
Cannabinoid receptor 1 EC50 = 25118.86 nM 4.6 Displacement of [35S]GTP-gamma-S from rat cerebellar CB1 receptor 16420041
HL-60 IC50 = 29000.0 nM 4.54 Inhibition of [3H]arachidonic acid production by stimulated HL60 cells. 11882004
THP-1 IC50 = 41000.0 nM 4.39 Concentration required to inhibit production of LTC4 from THP-1 cells stimulated... 11229777
THP-1 IC50 = 86000.0 nM 4.07 Concentration required to inhibit production of arachidonic acid from THP-1 cell... 11229777

Literature References

PubMed DOI Target Context # Activities
11229777 10.1016/s0960-894x(01)00003-8 Homo sapiens 5
19583260 10.1021/jm900461w Monoglyceride lipase 2
11229777 10.1016/s0960-894x(01)00003-8 THP-1 2
16420041 10.1021/jm0505157 Cannabinoid receptor 1 2
16078824 10.1021/jm058183t Fatty-acid amide hydrolase 1 1
38286094 10.1016/j.ejmech.2024.116176 RAW264.7 1
19883085 10.1021/jm901323s Fatty-acid amide hydrolase 1 1
19583260 10.1021/jm900461w Unchecked 1
19583260 10.1021/jm900461w Fatty-acid amide hydrolase 1 1
18321717 10.1016/j.bmc.2008.02.019 No relevant target 1
18321717 10.1016/j.bmc.2008.02.019 Liver 1
18321717 10.1016/j.bmc.2008.02.019 Cytosolic phospholipase A2 1
17320401 10.1016/j.bmc.2007.02.016 Cytosolic phospholipase A2 1
9276015 10.1021/jm960863w Bos taurus 1
11229777 10.1016/s0960-894x(01)00003-8 Cytosolic phospholipase A2 gamma 1
11882004 10.1021/jm011050x Cytosolic phospholipase A2 beta 1
11882004 10.1021/jm011050x No relevant target 1
11882004 10.1021/jm011050x HL-60 1
9341913 10.1021/jm970045j Cytosolic phospholipase A2 1
9341913 10.1021/jm970045j Unchecked 1

Data from ChEMBL 36 via Core Engine