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Compound Detail

CHEMBL113262

METHOXYARACHIDONOYL FLUOROPHOSPHONATE
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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCP(=O)(F)OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL113262
Name METHOXYARACHIDONOYL FLUOROPHOSPHONATE
Phase Preclinical
Structure Type MOL
InChI Key KWKZCGMJGHHOKJ-ZKWNWVNESA-N
10
Targets
19
Activities
1
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

370.5
MW (Da)
7.94
ALogP
2
HBA
0
HBD
26.3
PSA (Ų)
0.16
QED
1
Ro5 Violations
16
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H36FO2P
MW 370.49
Aromatic Rings 0
Heavy Atoms 25
NP-Likeness 0.70

Activity Summary

IC50 19 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Fatty-acid amide hydrolase 1
CHEMBL3455
 IC50 10.0 10.0 0.1 1
Fatty-acid amide hydrolase 1
CHEMBL2243
 IC50 9.48 9.12 0.3 4
Fatty-acid amide hydrolase 1
CHEMBL3229
 IC50 8.6 8.12 2.5 2
Monoacylglycerol lipase ABHD6
CHEMBL2189127
 IC50 7.77 7.77 17.0 1
Cannabinoid receptor 1
CHEMBL3571
 IC50 7.7 7.7 20.0 1
Monoglyceride lipase
CHEMBL4191
 IC50 7.6 7.5833 25.1 6
Unchecked
CHEMBL612545
 IC50 7.21 7.21 62.0 1
Platelet-activating factor acetylhydrolase IB subunit alpha2
CHEMBL4463
 IC50 7.14 7.14 72.0 1
Cannabinoid receptor 1
CHEMBL3037
 IC50 6.28 6.28 530.0 1
Cytosolic phospholipase A2
CHEMBL3816
 IC50 6.19 6.19 640.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 52.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Fatty-acid amide hydrolase 1 IC50 = 0.1 nM 10.0 Inhibitory potency of Fatty-acid amide hydrolase with Mouse brain membrane 12951114
Fatty-acid amide hydrolase 1 IC50 = 0.33 nM 9.48 Inhibition of human FAAH 19583260
Fatty-acid amide hydrolase 1 IC50 = 0.3311 nM 9.48 Inhibition of human recombinant FAAH-maltose binding protein 19883085
Fatty-acid amide hydrolase 1 IC50 = 1.0 nM 9.0 Inhibition of FAAH 22779702
Fatty-acid amide hydrolase 1 IC50 = 2.5 nM 8.6 Inhibitory potency of Fatty-acid amide hydrolase with rat brain membrane 12951114
Fatty-acid amide hydrolase 1 IC50 = 3.0 nM 8.52 Irreversible inhibition of fatty acid amide hydrolase; range=1-3 nM 16078824
Monoacylglycerol lipase ABHD6 IC50 = 17.0 nM 7.77 Inhibition of ABHD6 (unknown origin) 32371333
Cannabinoid receptor 1 IC50 = 20.0 nM 7.7 Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- ca... 12951114
Fatty-acid amide hydrolase 1 IC50 = 23.0 nM 7.64 Inhibition of FAAH from rat brain microsomes by RP-HPLC 20005725
Monoglyceride lipase IC50 = 25.12 nM 7.6 Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol sub... 25752982
Monoglyceride lipase IC50 = 25.12 nM 7.6 Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol sub... 25752982
Monoglyceride lipase IC50 = 26.3 nM 7.58 Inhibition of human MGL 19583260
Monoglyceride lipase IC50 = 26.3 nM 7.58 Inhibition of human MGL activity using [3H]2-oleoylglycerol substrate by liquid ... 19883085
Monoglyceride lipase IC50 = 26.3 nM 7.58 Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol sub... 25752982
Monoglyceride lipase IC50 = 27.54 nM 7.56 Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol sub... 25752982
Unchecked IC50 = 62.0 nM 7.21 inhibition of MAGL 20005725
Platelet-activating factor acetylhydrolase IB subunit alpha2 IC50 = 72.0 nM 7.14 Inhibition of PAFAH1B2 (unknown origin) using 2-thiol-PAF as substrate by Ellman... 27160052
Cannabinoid receptor 1 IC50 = 530.0 nM 6.28 Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- ca... 12951114
Cytosolic phospholipase A2 IC50 = 640.0 nM 6.19 Inhibition of cPLA2 from human platelets by RP-HPLC 20005725

Literature References

PubMed DOI Target Context # Activities
25752982 10.1016/j.bmcl.2015.02.037 Monoglyceride lipase 4
27160052 10.1016/j.bmc.2016.04.047 Platelet-activating factor acetylhydrolase IB subunit alpha2 3
12951114 10.1016/s0960-894x(03)00721-2 Fatty-acid amide hydrolase 1 2
20005725 10.1016/j.bmc.2009.11.028 Unchecked 2
19583260 10.1021/jm900461w Monoglyceride lipase 2
12951114 10.1016/s0960-894x(03)00721-2 Cannabinoid receptor 1 2
18657971 10.1016/j.bmcl.2008.06.091 Neutral cholesterol ester hydrolase 1 1
18657971 10.1016/j.bmcl.2008.06.091 Monoglyceride lipase 1
18657971 10.1016/j.bmcl.2008.06.091 Monoacylglycerol lipase ABHD6 1
18657971 10.1016/j.bmcl.2008.06.091 Lysophosphatidylserine lipase ABHD12 1
18657971 10.1016/j.bmcl.2008.06.091 Phosphatidylserine lipase ABHD16A 1
19719235 10.1021/jm900324e Fatty-acid amide hydrolase 1 1
18657971 10.1016/j.bmcl.2008.06.091 Fatty-acid amide hydrolase 1 1
19583260 10.1021/jm900461w Fatty-acid amide hydrolase 1 1
19583260 10.1021/jm900461w Unchecked 1
19883085 10.1021/jm901323s Fatty-acid amide hydrolase 1 1
19883085 10.1021/jm901323s Monoglyceride lipase 1
37976705 10.1016/j.ejmech.2023.115916 Lysophosphatidylserine lipase ABHD12 1
20005725 10.1016/j.bmc.2009.11.028 Fatty-acid amide hydrolase 1 1
18983142 10.1021/jm800311k Mus musculus 1

Data from ChEMBL 36 via Core Engine