Page last updated: 2024-12-10

glyceryl 2-arachidonate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

glyceryl 2-arachidonate: binds to cannabinoid receptors; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-arachidonoylglycerol : An endocannabinoid and an endogenous agonist of the cannabinoid receptors (CB1 and CB2). It is an ester formed from omega-6-arachidonic acid and glycerol. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID5282280
CHEMBL ID122972
CHEBI ID52392
SCHEMBL ID136277
MeSH IDM0248992

Synonyms (74)

Synonym
2-arachidonoylglycerol (2-ag)
1,3-dihydroxypropan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
chembl122972 ,
bdbm26144
BRD-K71198913-001-02-3
gtpl729
1,3-dihydroxy-2-propanyl (5z,8z,11z,14z)-5,8,11,14-eicosatetraenoate
[2-hydroxy-1-(hydroxymethyl)ethyl] (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
2-arachidonoyl glycerol
53847-30-6
2-arachidonoyl-sn-glycerol
5,8,11,14-eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (5z,8z,11z,14z)-
5,8,11,14-eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester, (all-z)-
2-ara-gl
2-arachidonoyl-glycerol
2-arachidonyl-glycerol
PDSP2_000790
2-monoarachidonoylglycerol
glyceryl 2-arachidonate
IDI1_033883
BSPBIO_001413
PDSP1_000803
(5z,8z,11z,14z)-eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
2-arachidonyl glycerol, ~10 mg/ml, >=98% (hplc)
2-arachidonylglycerol
NCGC00161389-03
NCGC00161389-01
NCGC00161389-02
2-ag
2-arachidonoylglycerol
NCGC00161389-04
2-(5z,8z,11z,14z-eicosatetraenoyl)-glycerol
CHEBI:52392 ,
HMS1989G15
5z,8z,11z,14z-eicosatetraenoic acid, 2-glyceryl ester
2-arachidonoylglycero
L000057
2-oarachidonoyl glycerol
BML3-F09
HMS1791G15
HMS1361G15
mg(0:0/20:4(5z,8z,11z,14z)/0:0)
2-(5z,8z,11z,14z-eicosatetraenoyl)-sn-glycerol
LMGL01010023
unii-8d239qdw64
8d239qdw64 ,
2-arachidonyl glycerol
FA028
SCHEMBL136277
(5z,8z,11z,14z)-5,8,11,14-eicosatetraenoic acid, 2-hydroxy-1-(hydroxymethyl)ethyl ester
W-204228
AKOS024456515
HMS3649C03
HMS3402G15
924894-97-3
(5z,8z,11z,14z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid
mg(0:0/20:4n6)
mag(0:0/20:4w6)
(5z,8z,11z,14z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate
mag(0:0/20:4n6)
2-(5z,8z,11z,14z-eicosatetraenoyl)-rac-glycerol
(all-z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoic acid
mg(0:0/20:4w6)
2-monoarachidonoylglycerolbeta-monoacylglycerol
HY-W011051
CS-W011767
Q209320
(all-z)-2-hydroxy-1-(hydroxymethyl)ethyl ester 5,8,11,14-eicosatetraenoate
sr-01000946555
SR-01000946555-1
DTXSID001017454
5z,8z,11z,14z-eicosatetraenoicacid,2-glycerol-1,1,2,3,3-d5ester
F85611
2-ag-d8

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" Of all the arsenic derivatives, arsenite is the one of the most toxic compounds."( Metabolomic assessment of arsenite toxicity and novel biomarker discovery in early development of zebrafish embryos.
Ho, SH; Huang, PL; Lai, YH; Lin, YC; Phan, NN; Tsai, CH; Wang, JC; Wu, SY; Yang, CH; Yu, HG, 2018
)
0.48

Compound-Compound Interactions

ExcerptReferenceRelevance
"A simple and reliable method was developed and validated to determine the endocannabinoids anandamide (AEA) and 2-arachidonoylglycerol (2-AG) in rat brain samples by micro salting-out assisted liquid-liquid extraction combined with ultra-high performance liquid chromatography tandem mass spectrometry (SALLLE/UHPLC-MS/MS)."( A micro salting-out assisted liquid-liquid extraction combined with ultra-high performance liquid chromatography tandem mass spectrometry to determine anandamide and 2-arachidonoylglycerol in rat brain samples.
Oliveira, IGC; Queiroz, MEC, 2020
)
0.56

Bioavailability

ExcerptReferenceRelevance
" Clinical trials are now required, but are hindered by a paucity of cannabinoids of suitable bioavailability and therapeutic ratio."( Cannabinoids and pain.
Rice, AS, 2001
)
0.31
" In this study, the exact modulation of MH on CB2 receptor activity was elucidated and its endocannabinoid substrate-specific inhibition (SSI) of cyclooxygenase-2 (COX-2) and CNS bioavailability are described for the first time."( 4'-O-methylhonokiol increases levels of 2-arachidonoyl glycerol in mouse brain via selective inhibition of its COX-2-mediated oxygenation.
Charles, RP; Chicca, A; Gachet, MS; Gertsch, J; Petrucci, V; Schuehly, W, 2015
)
0.42
" However, a large fraction of these n-3 PUFAs is present in the phospholipid (PL) fraction and may have high bioavailability and capacity to change the endocannabinoid profile."( Intake of a Western diet containing cod instead of pork alters fatty acid composition in tissue phospholipids and attenuates obesity and hepatic lipid accumulation in mice.
Fauske, KR; Fjære, E; Frøyland, L; Graff, IE; Kopecky, J; Kristiansen, K; Kuda, O; Liaset, B; Liisberg, U; Madsen, L; Myrmel, LS; Norberg, N, 2016
)
0.43
" Cocaine acts by altering DA bioavailability by targeting the DAT."( Glucagon-like peptide 1 receptor activation regulates cocaine actions and dopamine homeostasis in the lateral septum by decreasing arachidonic acid levels.
Bering, T; Bluett, RJ; Erreger, K; Fink-Jensen, A; Galli, A; Graham, D; Hackett, TA; Osses, N; Patel, S; Pino, JA; Reddy, IA; Reyes, JG; Stanwood, GD; Sørensen, G; Torres, GE; Valle, C; Weikop, P; Wortwein, G, 2016
)
0.43
" However, its bioavailability to the brain and potential central effects remain unexplored."( Neuropsychopharmacological profiling of scoparone in mice.
Budzyńska, B; El Sayed, NS; Gertsch, J; Kowalczyk, J; Kurach, Ł; Pellegata, D; Skalicka-Woźniak, K, 2022
)
0.72

Dosage Studied

ExcerptRelevanceReference
" To enhance efficacy differences, agonist dose-response curves were generated using increasing GDP concentrations."( Despite substantial degradation, 2-arachidonoylglycerol is a potent full efficacy agonist mediating CB(1) receptor-dependent G-protein activation in rat cerebellar membranes.
Järvinen, T; Laine, K; Laitinen, JT; Savinainen, JR, 2001
)
0.31
" Whether repeated dosing would achieve greater protection remains to be examined."( Endocannabinoid degradation inhibition improves neurobehavioral function, blood-brain barrier integrity, and neuroinflammation following mild traumatic brain injury.
Impastato, RA; Katz, PS; Molina, PE; Rogers, EK; Sulzer, JK; Teng, SX, 2015
)
0.42
"6 mg/kg) served as a discriminative stimulus in both genotypes, with similar THC dose-response curves between groups."( Phenotypic assessment of THC discriminative stimulus properties in fatty acid amide hydrolase knockout and wildtype mice.
Vann, RE; Walentiny, DM; Wiley, JL, 2015
)
0.42
" CPF inhibited ChE activity in spleen and liver (all dosages) and in brain (highest dosage only)."( Inhibition of Endocannabinoid-Metabolizing Enzymes in Peripheral Tissues Following Developmental Chlorpyrifos Exposure in Rats.
Alugubelly, N; Buntyn, RW; Carr, RL; Hybart, RL; Mohammed, AN; Nail, CA; Parker, GC; Ross, MK,
)
0.13
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human metaboliteAny mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
endocannabinoidA class of cannabinoids present in mammalian biological fluids and tissues that activate cannabinoid receptors.
2-acylglycerol 20:4A 2-monoglyceride in which the acyl group contains 20 carbons and 4 double bonds.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (11)

PathwayProteinsCompounds
Hemostasis23944
Platelet activation, signaling and aggregation6315
Effects of PIP2 hydrolysis110
Arachidonate production from DAG16
Signaling Pathways1269117
Signaling by GPCR24955
GPCR downstream signalling17252
G alpha (q) signalling events7928
Orexin receptor pathway2915
Cannabinoid receptor signaling020
Thermogenesis018

Protein Targets (16)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency0.01260.003245.467312,589.2998AID2517
Chain A, CruzipainTrypanosoma cruziPotency12.58930.002014.677939.8107AID1476
phosphopantetheinyl transferaseBacillus subtilisPotency3.54810.141337.9142100.0000AID1490
Microtubule-associated protein tauHomo sapiens (human)Potency25.11890.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
alpha-galactosidaseHomo sapiens (human)Potency50.11874.466818.391635.4813AID1467
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency28.18380.001815.663839.8107AID894
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
DNA polymerase kappa isoform 1Homo sapiens (human)Potency39.81070.031622.3146100.0000AID588579
histone acetyltransferase KAT2A isoform 1Homo sapiens (human)Potency39.81070.251215.843239.8107AID504327
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Fatty-acid amide hydrolase 1Homo sapiens (human)Ki5.00000.00061.27476.0000AID71609
Fatty acid-binding protein, liverMus musculus (house mouse)Ki0.06100.02100.34832.0000AID1802031
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.34800.00020.566510.0000AID1127485; AID1287160; AID49667
Cannabinoid receptor 1Homo sapiens (human)Ki0.60550.00010.50779.6000AID1363876; AID1630814; AID607136; AID633466
Cannabinoid receptor 2 Homo sapiens (human)Ki1.37500.00000.415610.0000AID1127483; AID1630815; AID607137; AID633467
Cannabinoid receptor 2Rattus norvegicus (Norway rat)Ki0.10000.02000.22060.9120AID49864
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cannabinoid receptor 1Homo sapiens (human)EC50 (µMol)0.02300.00010.12752.2400AID284759
Cannabinoid receptor 2 Homo sapiens (human)EC50 (µMol)0.01700.00030.15173.2800AID284761
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (43)

Processvia Protein(s)Taxonomy
fatty acid catabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
arachidonic acid metabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
positive regulation of vasoconstrictionFatty-acid amide hydrolase 1Homo sapiens (human)
monoacylglycerol catabolic processFatty-acid amide hydrolase 1Homo sapiens (human)
positive regulation of acute inflammatory response to antigenic stimulusCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-modulating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
spermatogenesisCannabinoid receptor 1Homo sapiens (human)
axonal fasciculationCannabinoid receptor 1Homo sapiens (human)
response to nutrientCannabinoid receptor 1Homo sapiens (human)
memoryCannabinoid receptor 1Homo sapiens (human)
positive regulation of neuron projection developmentCannabinoid receptor 1Homo sapiens (human)
negative regulation of serotonin secretionCannabinoid receptor 1Homo sapiens (human)
positive regulation of fever generationCannabinoid receptor 1Homo sapiens (human)
negative regulation of fatty acid beta-oxidationCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, GABAergicCannabinoid receptor 1Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 1Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 1Homo sapiens (human)
negative regulation of dopamine secretionCannabinoid receptor 1Homo sapiens (human)
response to nicotineCannabinoid receptor 1Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 1Homo sapiens (human)
response to cocaineCannabinoid receptor 1Homo sapiens (human)
glucose homeostasisCannabinoid receptor 1Homo sapiens (human)
positive regulation of apoptotic processCannabinoid receptor 1Homo sapiens (human)
response to ethanolCannabinoid receptor 1Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 1Homo sapiens (human)
negative regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
positive regulation of blood pressureCannabinoid receptor 1Homo sapiens (human)
regulation of insulin secretionCannabinoid receptor 1Homo sapiens (human)
regulation of synaptic transmission, glutamatergicCannabinoid receptor 1Homo sapiens (human)
maternal process involved in female pregnancyCannabinoid receptor 1Homo sapiens (human)
regulation of feeding behaviorCannabinoid receptor 1Homo sapiens (human)
regulation of penile erectionCannabinoid receptor 1Homo sapiens (human)
retrograde trans-synaptic signaling by endocannabinoidCannabinoid receptor 1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationCannabinoid receptor 1Homo sapiens (human)
trans-synaptic signaling by endocannabinoid, modulating synaptic transmissionCannabinoid receptor 1Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 1Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 1Homo sapiens (human)
response to amphetamineCannabinoid receptor 2 Homo sapiens (human)
inflammatory responseCannabinoid receptor 2 Homo sapiens (human)
immune responseCannabinoid receptor 2 Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerCannabinoid receptor 2 Homo sapiens (human)
leukocyte chemotaxisCannabinoid receptor 2 Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicCannabinoid receptor 2 Homo sapiens (human)
response to lipopolysaccharideCannabinoid receptor 2 Homo sapiens (human)
negative regulation of mast cell activationCannabinoid receptor 2 Homo sapiens (human)
cannabinoid signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
negative regulation of action potentialCannabinoid receptor 2 Homo sapiens (human)
regulation of metabolic processCannabinoid receptor 2 Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingFatty-acid amide hydrolase 1Homo sapiens (human)
phospholipid bindingFatty-acid amide hydrolase 1Homo sapiens (human)
fatty acid amide hydrolase activityFatty-acid amide hydrolase 1Homo sapiens (human)
identical protein bindingFatty-acid amide hydrolase 1Homo sapiens (human)
acylglycerol lipase activityFatty-acid amide hydrolase 1Homo sapiens (human)
amidase activityFatty-acid amide hydrolase 1Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 1Homo sapiens (human)
identical protein bindingCannabinoid receptor 1Homo sapiens (human)
G protein-coupled receptor activityCannabinoid receptor 1Homo sapiens (human)
protein bindingCannabinoid receptor 2 Homo sapiens (human)
cannabinoid receptor activityCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneFatty-acid amide hydrolase 1Homo sapiens (human)
cytoskeletonFatty-acid amide hydrolase 1Homo sapiens (human)
organelle membraneFatty-acid amide hydrolase 1Homo sapiens (human)
mitochondrial outer membraneCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
actin cytoskeletonCannabinoid receptor 1Homo sapiens (human)
growth coneCannabinoid receptor 1Homo sapiens (human)
presynaptic membraneCannabinoid receptor 1Homo sapiens (human)
membrane raftCannabinoid receptor 1Homo sapiens (human)
glutamatergic synapseCannabinoid receptor 1Homo sapiens (human)
GABA-ergic synapseCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 1Homo sapiens (human)
cytoplasmCannabinoid receptor 1Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
dendriteCannabinoid receptor 2 Homo sapiens (human)
extrinsic component of cytoplasmic side of plasma membraneCannabinoid receptor 2 Homo sapiens (human)
perikaryonCannabinoid receptor 2 Homo sapiens (human)
endoplasmic reticulumCannabinoid receptor 2 Homo sapiens (human)
plasma membraneCannabinoid receptor 2 Homo sapiens (human)
cytoplasmCannabinoid receptor 2 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (39)

Assay IDTitleYearJournalArticle
AID1626212Binding affinity to PDEA modified AGP (unknown origin) at 40 uM by surface plasmon resonance method2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID284761Agonist activity at CB2 receptor expressed in HL60 cells assessed as increase in intracellular free calcium concentrations2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.
AID143900Inhibition of N-arachidonoylethanolamine transporter (AEA) activity in human lymphoma U937 cell using [3H]AEA as substrate in the 0-1000 nM conc.2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase.
AID263853Efficacy at CB1 receptor in rat brain by [35S]GTPgammaS binding assay (basal value set at 100%)2006Bioorganic & medicinal chemistry letters, May-01, Volume: 16, Issue:9
Alpha-methylated derivatives of 2-arachidonoyl glycerol: synthesis, CB1 receptor activity, and enzymatic stability.
AID284762Antagonist activity at CB2 receptor expressed in HL60 cells assessed as abrogation of 2-archidonoylglycerol-induced increase in intracellular free calcium levels2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.
AID633468Selectivity index, ratio of Ki for human CB2 receptor to Ki for human CB1 receptor2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Resorcinol-sn-glycerol derivatives: novel 2-arachidonoylglycerol mimetics endowed with high affinity and selectivity for cannabinoid type 1 receptor.
AID38685Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID607136Displacement of [3H]-CP55940 from human CB1 receptor expressed in HEK-293-EBNA cell membranes after 90 mins by scintillation counting2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Development of endocannabinoid-based chemical probes for the study of cannabinoid receptors.
AID1127507Selectivity ratio of Ki for human CB2 receptor to Ki for rat CB1 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID607137Displacement of [3H]-CP55940 from human CB2 receptor expressed in HEK-293-EBNA cell membranes after 90 mins by scintillation counting2011Journal of medicinal chemistry, Jul-28, Volume: 54, Issue:14
Development of endocannabinoid-based chemical probes for the study of cannabinoid receptors.
AID1363876Binding affinity to CB1R (unknown origin)2017Journal of medicinal chemistry, 01-12, Volume: 60, Issue:1
Therapeutic Potential of Fatty Acid Amide Hydrolase, Monoacylglycerol Lipase, and N-Acylethanolamine Acid Amidase Inhibitors.
AID1626211Binding affinity to human serum albumin at 40 uM by surface plasmon resonance method2016Journal of medicinal chemistry, 07-28, Volume: 59, Issue:14
Chromenopyrazole, a Versatile Cannabinoid Scaffold with in Vivo Activity in a Model of Multiple Sclerosis.
AID263855Potency at CB1 receptor in rat brain by [35S]GTP-gamma-S binding assay2006Bioorganic & medicinal chemistry letters, May-01, Volume: 16, Issue:9
Alpha-methylated derivatives of 2-arachidonoyl glycerol: synthesis, CB1 receptor activity, and enzymatic stability.
AID1630814Binding affinity to CB1 receptor (unknown origin)
AID546207Antimicrobial activity against Hartmannella vermiformis assessed as number of viable cells/ml at 10 ug/ml upto 3 days by hemocytometer relative to control2010Antimicrobial agents and chemotherapy, Jul, Volume: 54, Issue:7
Endocannabinoids inhibit the growth of free-living amoebae.
AID49667Displacement of [3H]CP-55940 from rat forebrain membrane which expresses Cannabinoid receptor 1 in the presence of PMSF2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase.
AID309556Inhibition of partially purified Sprague-Dawley rat MGL assessed as substrate hydrolysis2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Conformationally constrained analogues of 2-arachidonoylglycerol.
AID309555Inhibition of partially purified Sprague-Dawley rat FAAH assessed as substrate hydrolysis2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Conformationally constrained analogues of 2-arachidonoylglycerol.
AID1127485Binding affinity to rat CB1 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID38682Tested for hydrolysis by rat brain microsomal anandamide amidohydrolase (AAH).1999Journal of medicinal chemistry, Mar-11, Volume: 42, Issue:5
Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase.
AID546206Antimicrobial activity against Acanthamoeba castellanii assessed as number of viable cells/ml at 10 ug/ml upto 3 days by hemocytometer relative to control2010Antimicrobial agents and chemotherapy, Jul, Volume: 54, Issue:7
Endocannabinoids inhibit the growth of free-living amoebae.
AID633467Displacement of [3H]CP55940 from human CB2 receptor expressed in human HEK293 cells2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Resorcinol-sn-glycerol derivatives: novel 2-arachidonoylglycerol mimetics endowed with high affinity and selectivity for cannabinoid type 1 receptor.
AID284759Agonist activity at CB1 receptor expressed in NG108-15 cells assessed as increase in intracellular free calcium concentrations2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.
AID49864Displacement of [3H]CP-55940 from rat forebrain membrane which expresses Cannabinoid receptor 2 in the presence of PMSF2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase.
AID546208Antimicrobial activity against Willaertia magna c2c Maky ATCC PTA-7824 assessed as number of viable cells/ml at 10 ug/ml upto 3 days by hemocytometer relative to control2010Antimicrobial agents and chemotherapy, Jul, Volume: 54, Issue:7
Endocannabinoids inhibit the growth of free-living amoebae.
AID284760Antagonist activity at CB1 receptor expressed in NG108-15 cells assessed as abrogation of 2-archidonoylglycerol-induced increase in intracellular free calcium levels2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand.
AID633466Displacement of [3H]CP55940 from human CB1 receptor expressed in human HEK293 cells2011Journal of medicinal chemistry, Dec-22, Volume: 54, Issue:24
Resorcinol-sn-glycerol derivatives: novel 2-arachidonoylglycerol mimetics endowed with high affinity and selectivity for cannabinoid type 1 receptor.
AID1287160Displacement of [3H]CP55940 from CB1 receptor in Wistar rat brain incubated for 60 mins by radioactive filter binding assay2016European journal of medicinal chemistry, Apr-13, Volume: 112Tricyclic pyrazoles. Part 8. Synthesis, biological evaluation and modelling of tricyclic pyrazole carboxamides as potential CB2 receptor ligands with antagonist/inverse agonist properties.
AID71609Inhibition of Fatty-acid amide hydrolase (FAAH) activity in human lymphoma U937 cell using [3H]AEA as substrate in the 0-25 uM conc2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Oxygenated metabolites of anandamide and 2-arachidonoylglycerol: conformational analysis and interaction with cannabinoid receptors, membrane transporter, and fatty acid amide hydrolase.
AID1630815Binding affinity to CB2 receptor (unknown origin)
AID1127483Binding affinity to human CB2 receptor2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID588519A screen for compounds that inhibit viral RNA polymerase binding and polymerization activities2011Antiviral research, Sep, Volume: 91, Issue:3
High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors.
AID540299A screen for compounds that inhibit the MenB enzyme of Mycobacterium tuberculosis2010Bioorganic & medicinal chemistry letters, Nov-01, Volume: 20, Issue:21
Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.
AID1346753Rat CB1 receptor (Cannabinoid receptors)1995Biochemical pharmacology, Jun-29, Volume: 50, Issue:1
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
AID1346728Human CB2 receptor (Cannabinoid receptors)1995Biochemical pharmacology, Jun-29, Volume: 50, Issue:1
Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors.
AID1346728Human CB2 receptor (Cannabinoid receptors)1998European journal of pharmacology, Jul-17, Volume: 353, Issue:1
An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity.
AID1345070Human GPR55 (GPR18, GPR55 and GPR119)2007British journal of pharmacology, Dec, Volume: 152, Issue:7
The orphan receptor GPR55 is a novel cannabinoid receptor.
AID1346753Rat CB1 receptor (Cannabinoid receptors)1998European journal of pharmacology, Jul-17, Volume: 353, Issue:1
An entourage effect: inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity.
AID1802031FABP1 Fluorescent Ligand Displacement Assay from Article 10.1021/acs.biochem.6b00446: \\FABP1: A Novel Hepatic Endocannabinoid and Cannabinoid Binding Protein.\\2016Biochemistry, 09-20, Volume: 55, Issue:37
FABP1: A Novel Hepatic Endocannabinoid and Cannabinoid Binding Protein.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,215)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's40 (3.29)18.2507
2000's401 (33.00)29.6817
2010's672 (55.31)24.3611
2020's102 (8.40)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.07

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index8.07 (24.57)
Research Supply Index7.13 (2.92)
Research Growth Index5.19 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.07)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials10 (0.81%)5.53%
Reviews145 (11.77%)6.00%
Case Studies0 (0.00%)4.05%
Observational3 (0.24%)0.25%
Other1,074 (87.18%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]