Page last updated: 2024-12-11

noladin ether

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

Description

noladin ether: a cannabinoid CB1 receptor agonist; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

2-arachidonyl glyceryl ether : A monoalkylglycerol that is glycerol which is substituted by a (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl group at position 2. [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 CID6483057
CHEMBL ID146346
CHEBI ID75913
SCHEMBL ID495999
MeSH IDM0385362

Synonyms (48)

Synonym
2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoxy]propane-1,3-diol
1,3-propanediol, 2-[(5z,8z,11z,14z)-5,8,11,14-eicosatetraenyloxy]-
noladin ether
222723-55-9
noladin
c15h20n2o4s
NCGC00162416-01
chebi:75913 ,
hu-310
CHEMBL146346 ,
2-[((5z,8z,11z)-icosa-5,8,11,14-tetraenyl)oxy]-propane-1,3-diol
bdbm50171296
2-[((11z,14z)-icosa-5,8,11,14-tetraenyl)oxy]-propane-1,3-diol
2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenyloxy]propane-1,3-diol
1,3-propanediol, 2-((5z,8z,11z,14z)-5,8,11,14-eicosatetraenyloxy)-
0d295flv8w ,
unii-0d295flv8w
2-arachidonyl glyceryl ether
2-(5z,8z,11z,14z-eicosatetraenyl)-sn-glycerol
2-arachidonyl glycerol ether
(5z,8z,11z,14z)-icosatetraenyl-2-glyceryl ether
2-o-(5z,8z,11z,14z)-eicosatetraenylglycerol
5z,8z,11z,14z-eicosatetraen-2-glyceryl ether
2-ag ether
2-[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraen-1-yloxy]propane-1,3-diol
gtpl5545
hu 310
2-arachidonylglyceryl ether
1,3-propanediol, 2-((5z,8z,11z,14z)-5,8,11,14-eicosatetraen-1-yloxy)-
SCHEMBL495999
2-[(5z,8z,11z,14z)-eicosatetraenyloxy]-1,3-propanediol
CUJUUWXZAQHCNC-DOFZRALJSA-N
HB0988
AKOS024456581
HMS3649C05
5z,?8z,?11z,?14z-?eicosatetraen-?2-?glyceryl ether
2-o-(5z,8z,11z,14z-eicosatetraenyl)-sn-glycerol
LMGL01020034
Q3877880
SR-01000946556-1
sr-01000946556
DTXSID901018178
2-arachidonoyl glyceryl ether
2-{[(5z,8z,11z,14z)-icosa-5,8,11,14-tetraen-1-yl]oxy}propane-1,3-diol
VKV ,
HY-110014
CS-0032829
PD020897

Research Excerpts

Overview

Noladin ether (NE) is a putative endogenously occurring cannabinoid demonstrating agonist activity at CB1 receptors.

ExcerptReferenceRelevance
"Noladin ether (NE) is a putative endogenously occurring cannabinoid demonstrating agonist activity at CB1 receptors. "( The endocannabinoid noladin ether acts as a full agonist at human CB2 cannabinoid receptors.
Joseph, BK; Mayeux, PR; Prather, PL; Ruckle, MB; Shoemaker, JL, 2005
)
2.09

Effects

ExcerptReferenceRelevance
"1 Noladin ether has recently been reported to be an endocannabinoid, with selectivity for the cannabinoid (CB) CB1 receptor. "( Noladin ether, a putative endocannabinoid, attenuates sensory neurotransmission in the rat isolated mesenteric arterial bed via a non-CB1/CB2 G(i/o) linked receptor.
Duncan, M; Kendall, DA; Millns, P; Ralevic, V; Smart, D; Wright, JE, 2004
)
2.49
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (3)

ClassDescription
monoalkylglycerolAn ether lipid that is glycerol carrying a single alkyl substituent in an unspecified position.
endocannabinoidA class of cannabinoids present in mammalian biological fluids and tissues that activate cannabinoid receptors.
2-alkylglycerolA monoalkylglycerol that is a derivative of glycerol in which the hydroxy group at position 2 has been converted to an ether.
[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]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency31.62285.623417.292931.6228AID485281
Chain A, CruzipainTrypanosoma cruziPotency25.11890.002014.677939.8107AID1476
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency23.75580.011212.4002100.0000AID1030
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa)Homo sapiens (human)Potency28.18380.016525.307841.3999AID602332
DNA polymerase kappa isoform 1Homo sapiens (human)Potency25.11890.031622.3146100.0000AID588579
[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)
Cannabinoid receptor 1Rattus norvegicus (Norway rat)Ki0.02100.00020.566510.0000AID1127502; AID238320
Cannabinoid receptor 1Homo sapiens (human)Ki0.02250.00010.50779.6000AID607136; AID633466
Cannabinoid receptor 2 Homo sapiens (human)Ki2.33330.00000.415610.0000AID1127483; AID607137; AID633467
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (39)

Processvia Protein(s)Taxonomy
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 (4)

Processvia Protein(s)Taxonomy
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 (13)

Processvia Protein(s)Taxonomy
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 (14)

Assay IDTitleYearJournalArticle
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.
AID30235Chemical stability in TRIS buffers at pH 7.4 at 37 C was determined; Not determined2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether.
AID1127502Displacement of [3H]HU-243 from CB1 receptor of rat brain synaptosomal membranes2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID238320Binding affinity for cannabinoid receptor 12005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.
AID1127508Selectivity ratio of Ki for human CB2 receptor to Ki for CB1 receptor of rat brain synaptosomal membranes2013Journal of medicinal chemistry, Nov-14, Volume: 56, Issue:21
Therapeutic utility of cannabinoid receptor type 2 (CB(2)) selective agonists.
AID30232Chemical stability in phosphate buffers at pH 7.4 at 37 C was determined; Not determined2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether.
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.
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.
AID28663Aqueous solubility of the phosphate in TRIS buffers at pH 7.4 at 37 C was determined2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether.
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.
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.
AID28669Calculated partition coefficient (clogD7.4) (ACDLabs log D suite)2003Journal of medicinal chemistry, Nov-06, Volume: 46, Issue:23
Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether.
AID1345070Human GPR55 (GPR18, GPR55 and GPR119)2007British journal of pharmacology, Dec, Volume: 152, Issue:7
The orphan receptor GPR55 is a novel cannabinoid receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's27 (69.23)29.6817
2010's11 (28.21)24.3611
2020's1 (2.56)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 28.29

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index28.29 (24.57)
Research Supply Index3.71 (2.92)
Research Growth Index4.38 (4.65)
Search Engine Demand Index31.18 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (28.29)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (7.50%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (92.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]