Compounds > methyl arachidonylfluorophosphonate
Page last updated: 2024-08-02 16:40:24

methyl arachidonylfluorophosphonate

Description

Methyl Arachidonyl Fluorophosphonate : no description available [CHeBI]

Cross-References

ID SourceID
PubMed CID10429254
CHEMBL ID113262
SCHEMBL ID22222736
CHEBI ID188708
MeSH IDM0273634

Synonyms (39)

Synonym
HSCI1_000023
methyl arachidonyl fluorophosphonate
mafp
methoxy arachidonyl fluorophosphonate
NCGC00162418-01
methyl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenylphosphonofluoridate
bdbm50132713
methyl ((5z,8z,11z,14z)-2-icosa-5,8,11,14-tetraenyl)phosphonofluoridoate
arachidonic acid derivative
methyl -icosa-5,8,11,14-tetraenylphosphonofluoridate
methyl(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenylphosphonofluoridate
methyl arachidonoyl fluorophophonate
methylarachidonyl fluorophosphonate
methoxyarachidonoyl fluorophosphonate
CHEMBL113262 ,
CHEBI:188708
(5z,8z,11z,14z)-1-[luoro(methoxy)phosphoryl]icosa-5,8,11,14-tetraene
188404-10-6
(5z,8z,11z,14z)-5,8,11,14-eicosatetraenyl-methyl ester phosphonofluoridic acid
5z,8z,11z,14z-eicosatetraenyl-phosphonofluoridic acid, methyl ester
KWKZCGMJGHHOKJ-ZKWNWVNESA-N
phosphonofluoridic acid, p-(5z,8z,11z,14z)-5,8,11,14-eicosatetraen-1-yl-, methyl ester
AKOS024456588
HMS3649A10
c21h36fo2p
phosphonofluoridicacid,p-(5z,8z,11z,14z)-5,8,11,14-eicosatetraen-1-yl-,methyl ester
J-012140
SCHEMBL22222736
sr-01000946590
SR-01000946590-1
Q6823894
HY-103334
CS-0027666
(all-z)-5,8,11,14-eicosatetraenylphosphonofluoridic acid methyl ester
(5z,8z,11z,14z)-1-[fluoro(methoxy)phosphoryl]icosa-5,8,11,14-tetraene
methyl ((5z,8z,11z,14z)-icosa-5,8,11,14-tetraen-1-yl)phosphonofluoridate
AT25415
methylphosphonofluoridic acid 5,8,11,14-eicosatetraenyl ester
(all-z)-5,8,11,14-eicosatetraenylphosphonofluoridicacidmethylester

Drug Classes (1)

ClassDescription
phosphonic esterA phosphonic acid derivative in which one or both OH groups have been esterified.

Protein Targets (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency25.1189AID485281
Chain A, CruzipainTrypanosoma cruziPotency25.1189AID1476
phosphopantetheinyl transferaseBacillus subtilisPotency1.4125AID1490
Microtubule-associated protein tauHomo sapiens (human)Potency22.3872AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency35.4813AID1030
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency50.1187AID602332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency44.6684AID504847
DNA polymerase kappa isoform 1Homo sapiens (human)Potency28.1838AID588579
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency39.8107AID504327
Polyunsaturated fatty acid lipoxygenase ALOX15BHomo sapiens (human)Potency4.4668AID881
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency4.4668AID881

Inhibition Measurements

ProteinTaxonomyMeasurementAverage (mM)Bioassay(s)
Fatty-acid amide hydrolase 1Homo sapiens (human)IC500.0012AID242242; AID439742; AID441698; AID697523
Neuronal acetylcholine receptor subunit alpha-4Rattus norvegicus (Norway rat)IC500.6400AID460727
Neuronal acetylcholine receptor subunit beta-2Rattus norvegicus (Norway rat)IC500.6400AID460727
Cytosolic phospholipase A2Homo sapiens (human)IC500.6400AID460727
Platelet-activating factor acetylhydrolase IB subunit alpha2Homo sapiens (human)IC500.0720AID1312659
Fatty-acid amide hydrolase 1Rattus norvegicus (Norway rat)IC500.0230AID460725
Monoglyceride lipaseHomo sapiens (human)IC500.0261AID1193642; AID1193643; AID1193644; AID1193645; AID439741; AID441697

Bioassays (41)

Assay IDTitleYearJournalArticle
AID1910303Inhibition of FAAH in mouse brain membrane at 10 uM using TAMRA-FP serine hydrolase probe as substrate preincubated for 25 mins followed by substrate addition and measured after 25 mins SDS-PAGE analysis2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
ISSN: 1520-4804		Reversible Monoacylglycerol Lipase Inhibitors: Discovery of a New Class of Benzylpiperidine Derivatives.
AID1193644Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol substrate assessed as arachidonic acid after 60 mins by HPLC analysis2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405		Loratadine analogues as MAGL inhibitors.
AID1312656Inhibition of FP-Rh probe binding to PME-1 (unknown origin) at 685 nM incubated for 30 mins followed by FP-Rh probe addition measured after 30 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID409633Inhibition of MAGL in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID460729inhibition of MAGL2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
ISSN: 1464-3391		1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase.
AID460727Inhibition of cPLA2 from human platelets by RP-HPLC2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
ISSN: 1464-3391		1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase.
AID441792Selectivity ratio for human MGL activity to human recombinant FAAH2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
ISSN: 1520-4804		Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors.
AID697523Inhibition of FAAH2012Journal of medicinal chemistry, Aug-09, Volume: 55, Issue:15
ISSN: 1520-4804		Discovery of potent inhibitors of human and mouse fatty acid amide hydrolases.
AID441697Inhibition of human MGL activity using [3H]2-oleoylglycerol substrate by liquid scintillation counting2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
ISSN: 1520-4804		Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors.
AID439752Inhibition of [3H]2-OG binding to human MGL at 40 times IC50 treated for 1 hr before addition of 2-OG by liquid scintillation counting2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
ISSN: 1520-4804		Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
AID1193642Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol substrate assessed as arachidonic acid after 10 mins by HPLC analysis2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405		Loratadine analogues as MAGL inhibitors.
AID1910302Inhibition of human recombinant MAGL in mouse brain membrane at 10 uM using TAMRA-FP serine hydrolase probe as substrate preincubated for 25 mins followed by substrate addition and measured after 25 mins SDS-PAGE analysis2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
ISSN: 1520-4804		Reversible Monoacylglycerol Lipase Inhibitors: Discovery of a New Class of Benzylpiperidine Derivatives.
AID71610Inhibitory potency of Fatty-acid amide hydrolase with Mouse brain membrane2003Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19
ISSN: 0960-894X		Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors.
AID1312654Inhibition of FP-Rh probe binding to PAFAH1B3 (unknown origin) at 685 nM incubated for 30 mins followed by FP-Rh probe addition measured after 30 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID460730inhibition of MAGL up to 10 uM2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
ISSN: 1464-3391		1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase.
AID439743Selectivity ratio of IC50 for human FAAH to IC50 for human MGL2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
ISSN: 1520-4804		Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
AID1910305Inhibition of ABHD12 in mouse brain membrane at 10 uM using TAMRA-FP serine hydrolase probe as substrate preincubated for 25 mins followed by substrate addition and measured after 25 mins SDS-PAGE analysis2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
ISSN: 1520-4804		Reversible Monoacylglycerol Lipase Inhibitors: Discovery of a New Class of Benzylpiperidine Derivatives.
AID1193645Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol substrate assessed as arachidonic acid after 90 mins by HPLC analysis2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405		Loratadine analogues as MAGL inhibitors.
AID409634Inhibition of ABHD6 in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID1193643Reversible inhibition of human recombinant MAGL using 2-arachidonoylglycerol substrate assessed as arachidonic acid after 30 mins by HPLC analysis2015Bioorganic & medicinal chemistry letters, Apr-01, Volume: 25, Issue:7
ISSN: 1464-3405		Loratadine analogues as MAGL inhibitors.
AID1312648Inhibition of FP-Rh probe binding to PAFAH1B2 (unknown origin) at 150 nM incubated for 30 mins followed by FP-Rh probe addition measured after 30 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID242242Irreversible inhibition of fatty acid amide hydrolase; range=1-3 nM2005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
ISSN: 0022-2623		The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.
AID409631Inhibition of FAAH in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID460725Inhibition of FAAH from rat brain microsomes by RP-HPLC2010Bioorganic & medicinal chemistry, Jan-15, Volume: 18, Issue:2
ISSN: 1464-3391		1-Indol-1-yl-propan-2-ones and related heterocyclic compounds as dual inhibitors of cytosolic phospholipase A(2)alpha and fatty acid amide hydrolase.
AID1312659Inhibition of PAFAH1B2 (unknown origin) using 2-thiol-PAF as substrate by Ellman's assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID49331Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- cannabinoid as radioligand with mouse brain membrane2003Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19
ISSN: 0960-894X		Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors.
AID1558806Irreversible inhibition of recombinant rat MGL expressed in human HeLa cells at 20 nM using 2-oleoylglycerol as substrate preincubated for 20 mins followed by 100 fold dilution in presence of substrate by LC-MS analysis-based rapid dilution assay2020Journal of medicinal chemistry, 02-13, Volume: 63, Issue:3
ISSN: 1520-4804		Benzisothiazolinone Derivatives as Potent Allosteric Monoacylglycerol Lipase Inhibitors That Functionally Mimic Sulfenylation of Regulatory Cysteines.
AID441698Inhibition of human recombinant FAAH-maltose binding protein2009Journal of medicinal chemistry, Nov-26, Volume: 52, Issue:22
ISSN: 1520-4804		Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors.
AID420417Inhibition of rat recombinant FAAH2009Journal of medicinal chemistry, Aug-13, Volume: 52, Issue:15
ISSN: 1520-4804		Synthesis, in vitro and in vivo evaluation, and radiolabeling of aryl anandamide analogues as candidate radioligands for in vivo imaging of fatty acid amide hydrolase in the brain.
AID409635Inhibition of ABHD12 in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID439742Inhibition of human FAAH2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
ISSN: 1520-4804		Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
AID346661Half life in mouse brain2008Journal of medicinal chemistry, Dec-11, Volume: 51, Issue:23
ISSN: 1520-4804		Discovery and development of fatty acid amide hydrolase (FAAH) inhibitors.
AID409632Inhibition of KIAA1363 in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID1312658Inhibition of FP-Rh probe binding to PAFAH1B2 (unknown origin) doped in human HeLa cell lysate at 685 nM incubated for 30 mins followed by FP-Rh probe addition measured after 10 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID49479Binding affinity towards Cannabinoid receptor 1 was determined using [3H]-CP- cannabinoid as radioligand with rat brain membrane2003Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19
ISSN: 0960-894X		Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors.
AID1312655Inhibition of FP-Rh probe binding to FAM108B (unknown origin) at 685 nM incubated for 30 mins followed by FP-Rh probe addition measured after 30 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID1312657Inhibition of FP-Rh probe binding to RBBP9 (unknown origin) at 685 nM incubated for 30 mins followed by FP-Rh probe addition measured after 30 mins by ABPP gel-based assay2016Bioorganic & medicinal chemistry, 09-01, Volume: 24, Issue:17
ISSN: 1464-3391		Identification of selective covalent inhibitors of platelet activating factor acetylhydrolase 1B2 from the screening of an oxadiazolone-capped peptoid-azapeptoid hybrid library.
AID439741Inhibition of human MGL2009Journal of medicinal chemistry, Dec-10, Volume: 52, Issue:23
ISSN: 1520-4804		Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors.
AID1910304Inhibition of ABHD6 in mouse brain membrane at 10 uM using TAMRA-FP serine hydrolase probe as substrate preincubated for 25 mins followed by substrate addition and measured after 25 mins SDS-PAGE analysis2022Journal of medicinal chemistry, 05-26, Volume: 65, Issue:10
ISSN: 1520-4804		Reversible Monoacylglycerol Lipase Inhibitors: Discovery of a New Class of Benzylpiperidine Derivatives.
AID409636Inhibition of BAT5 in mouse brain at 0.01 to 100 uM treated for 30 mins by SDS-PAGE using rhodamine-tagged FP probe2008Bioorganic & medicinal chemistry letters, Nov-15, Volume: 18, Issue:22
ISSN: 1464-3405		Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling.
AID71615Inhibitory potency of Fatty-acid amide hydrolase with rat brain membrane2003Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19
ISSN: 0960-894X		Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors.

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's7 (53.85)29.6817
2010's4 (30.77)24.3611
2020's2 (15.38)2.80

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (15.38%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (84.62%)84.16%
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
trichlorfon
0
organic phosphonate;
organochlorine compound;
phosphonic ester		agrochemical;
anthelminthic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
insecticide		00low000000
soman
0
phosphonic ester00low000000
phenylphosphonothioic acid, 2-ethyl 2-(4-nitrophenyl) ester
0
organic phosphonate;
organothiophosphate insecticide;
phosphonic ester		acaricide;
agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor		00low000000
leptophos
0
bromobenzenes;
dichlorobenzene;
organic phosphonate;
phosphonic ester		00low000000
isofenphos
0
isopropyl ester;
organic phosphonate;
organothiophosphate insecticide;
phosphonic ester;
salicylates		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor		00low000000
armin
0
organic phosphonate;
phosphonic ester		00low000000
bay 93820
0
isopropyl ester;
organic phosphonate;
organothiophosphate insecticide;
phosphonic ester;
salicylates		agrochemical;
avicide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor		00low000000
fosthiazate
0
organic phosphonate;
organothiophosphate insecticide;
phosphonic ester		agrochemical;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
nematicide		00low000000
SubstanceStudiesClassesRolesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
am 251
1
amidopiperidine;
carbohydrazide;
dichlorobenzene;
organoiodine compound;
pyrazoles		antidepressant;
antineoplastic agent;
apoptosis inducer;
CB1 receptor antagonist		201520159.0low000010
cannabinol
1
dibenzopyran2005200519.0low000100
disulfiram
1
organic disulfide;
organosulfur acaricide		angiogenesis inhibitor;
antineoplastic agent;
apoptosis inducer;
EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor;
EC 3.1.1.1 (carboxylesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
EC 5.99.1.2 (DNA topoisomerase) inhibitor;
ferroptosis inducer;
fungicide;
NF-kappaB inhibitor		2009200915.0low000100
loratadine
1
benzocycloheptapyridine;
ethyl ester;
N-acylpiperidine;
organochlorine compound;
tertiary carboxamide		anti-allergic agent;
cholinergic antagonist;
geroprotector;
H1-receptor antagonist		201520159.0low000010
ethylmaleimide
1
maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor		2009200915.0low000100
phenylmethylsulfonyl fluoride
2
acyl fluorideserine proteinase inhibitor2005200817.5low000200
propofol
2
phenolsanticonvulsant;
antiemetic;
intravenous anaesthetic;
radical scavenger;
sedative		2005200817.5low000200
pyrilamine
1
aromatic ether;
ethylenediamine derivative		H1-receptor antagonist201520159.0low000010
1,6-bis(cyclohexyloximinocarbonyl)hexane
1
carbamate ester;
organonitrogen compound		2008200816.0low000100
thiram
1
organic disulfideantibacterial drug;
antifungal agrochemical;
antiseptic drug		2009200915.0low000100
carbaryl
1
carbamate ester;
naphthalenes		acaricide;
agrochemical;
carbamate insecticide;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant growth retardant		2008200816.0low000100
bis(1-piperidylthiocarbonyl)disulfide
1
2009200915.0low000100
tetramethylthiuram monosulfide
1
2009200915.0low000100
4,4'-dithiodimorpholine
1
2009200915.0medium000100
methyl diethyldithiocarbamate
1
2009200915.0low000100
n-phenylmaleimide
1
2009200915.0low000100
dronabinol
1
benzochromene;
diterpenoid;
phytocannabinoid;
polyketide		cannabinoid receptor agonist;
epitope;
hallucinogen;
metabolite;
non-narcotic analgesic		2005200519.0low000100
1,2-benzisothiazoline-3-one
1
organic heterobicyclic compound;
organonitrogen heterocyclic compound		disinfectant;
drug allergen;
environmental contaminant;
platelet aggregation inhibitor;
sensitiser;
xenobiotic		202020204.0low000010
1,6-bismaleimidohexane
1
2009200915.0low000100
gemcitabine
1
organofluorine compound;
pyrimidine 2'-deoxyribonucleoside		antimetabolite;
antineoplastic agent;
antiviral drug;
DNA synthesis inhibitor;
EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor;
environmental contaminant;
immunosuppressive agent;
photosensitizing agent;
prodrug;
radiosensitizing agent;
xenobiotic		202220222.0low000001
n-phenylphthalimide
1
2009200915.0low000100
n-methylmaleimide
1
2009200915.0low000100
n-benzylmaleimide
1
2009200915.0low000100
n,n'-4-phenylenedimaleimide
1
2009200915.0low000100
n-(2-methoxyphenyl)maleimide
1
2009200915.0high000100
cp-55,940
1
2005200519.0low000100
n-(4-bromophenyl)maleimide
1
2009200915.0high000100
arachidonic acid
1
icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite		2008200816.0low000100
oleic acid
1
octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent		2008200816.0low000100
cannabidiol
1
olefinic compound;
phytocannabinoid;
resorcinols		antimicrobial agent;
plant metabolite		2005200519.0low000100
urb 597
4
biphenyls2008202211.0low000211
thiopental
1
barbituratesanticonvulsant;
drug allergen;
environmental contaminant;
intravenous anaesthetic;
sedative;
xenobiotic		2008200816.0low000100
orlistat
4
beta-lactone;
carboxylic ester;
formamides;
L-leucine derivative		anti-obesity agent;
bacterial metabolite;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
EC 3.1.1.3 (triacylglycerol lipase) inhibitor		2005202211.5low000211
2-octyl-gamma-bromoacetoacetate
1
2008200816.0high000100
sr 144528
1
bridged compound;
monochlorobenzenes;
pyrazoles;
secondary carboxamide		CB2 receptor antagonist;
EC 2.3.1.26 (sterol O-acyltransferase) inhibitor		201520159.0low000010
arachidonyltrifluoromethane
4
fatty acid derivative;
ketone;
olefinic compound;
organofluorine compound		EC 3.1.1.4 (phospholipase A2) inhibitor2005201015.8low000400
anandamide
4
endocannabinoid;
N-acylethanolamine 20:4		human blood serum metabolite;
neurotransmitter;
vasodilator agent		2003200917.8low000400
arachidonyl dopamine
1
catechols;
fatty amide;
N-(fatty acyl)-dopamine;
secondary carboxamide		2005200519.0low000100
homo-gamma-linolenylethanolamide
1
N-acylethanolamine 20:32005200519.0low000100
7,10,13,16-docosatetraenylethanolamide
1
N-acylethanolamine 22:42005200519.0low000100
oleylamide
2
primary fatty amidehuman metabolite;
plant metabolite		2005200817.5low000200
n-arachidonylglycine
1
fatty amide;
N-acylglycine		2005200519.0low000100
linoleoyl ethanolamide
1
N-acylethanolamine 18:2EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor2009200915.0low000100
arachidonyl-2-chloroethylamide
1
fatty amide;
organochlorine compound;
secondary carboxamide;
synthetic cannabinoid		CB1 receptor agonist;
CB2 receptor agonist;
neuroprotective agent		2008200816.0low000100
(3r)-((2,3-dihydro-5-methyl-3-((4-morpholinyl)methyl)pyrrolo-(1,2,3-de)-1,4-benzoxazin-6-yl)(1-naphthalenyl))methanone
1
morpholines;
naphthyl ketone;
organic heterotricyclic compound;
synthetic cannabinoid		analgesic;
apoptosis inhibitor;
neuroprotective agent		2005200519.0low000100
virodhamine
1
fatty acid ester2005200519.0low000100
6-(bromomethylene)tetrahydro-3-(1-naphthaleneyl)-2h-pyran-2-one
2
naphthalenes2005200817.5low000200
noladin ether
1
2-alkylglycerol;
endocannabinoid;
monoalkylglycerol		2005200519.0low000100
am 404
1
anilide2005200519.0low000100
hu 210
1
1-benzopyran201520159.0low000010
sr 147778
1
pyrazoles;
ring assembly		2005200519.0low000100
cay 10499
1
carbamate ester2009200915.0low000100
arachidonoylserotonin
1
N-acylserotonin;
phenols		anti-inflammatory agent;
anticonvulsant;
antioxidant;
capsaicin receptor antagonist;
EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor;
human metabolite;
signalling molecule		2005200519.0low000100
urb 524
1
2008200816.0medium000100
ol-135
2
2008201214.0low000110
urb602
2
2009200915.0low000200
ly2183240
3
biphenyls2008200915.3high000300
wwl70
1
202220222.0medium000001
jzl 184
3
benzodioxoles200920227.0low000111
ConditionIndicatedStudiesFirst YearLast YearAverage AgeRelationship StrengthTrialspre-19901990's2000's2010'spost-2020
Allodynia0
1
2012201212.0high000010
Cancer of Pancreas0
1
202220222.0high000001
Pancreatic Neoplasms0
1
202220222.0high000001