Page last updated: 2024-12-10

homo-gamma-linolenylethanolamide

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Description

homo-gamma-linolenylethanolamide: found in brain; binds to the cannabinoid receptor; RN given for (Z,Z,Z)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5282272
CHEMBL ID121229
CHEBI ID34488
SCHEMBL ID14106447
MeSH IDM0222429

Synonyms (57)

Synonym
BRD-K78280988-001-02-2
IDI1_034001
BSPBIO_001531
hglea
homo-gamma-linolenylethanolamide
dihomo-gamma-linolenoylethanol amide
LMFA08040011
dihomo-gamma-linolenoyl-ea
NCGC00161194-05
NCGC00161194-04
NCGC00161194-03
n-(8z,11z,14z-eicosatrienoyl)-ethanolamine
8,11,14-eicosatrienoylethanolamide
NCGC00161194-06
HMS1989M13
150314-34-4
CHEBI:34488 ,
anandamide (20.3,n-6)
n-(8z,11z,14z-icosatrienoyl)-ethanolamide
(z,z,z)-icosa-8,11,14-trienoylethanolamide
(8z,11z,14z)-n-(2-hydroxyethyl)icosa-8,11,14-trienamide
dihomo-gamma-linolenoyl ethanolamide
CHEMBL121229 ,
anandamide (20:3,n-6)
BML2-B12
HMS1361M13
HMS1791M13
bdbm50056457
8,11,14-eicosatrienamide, n-(2-hydroxyethyl)-, (z,z,z)-
homo-gamma-linolenoyl ethanolamide
(z,z,z)-n-(2-hydroxyethyl)-8,11,14-eicosatrienamide
dihomo-gamma-linolenylethanolamide
n-homo-gamma-linolenoylethanolamine
gtpl5444
n-dihomo-gamma -linolenoylethanolamine
SCHEMBL14106447
ULQWKETUACYZLI-QNEBEIHSSA-N
n-(2-hydroxyethyl)-8z,11z,14z-eicosatrienamide
8,11,14-eicosatrienamide, n-(2-hydroxyethyl)-, (8z,11z,14z)-
dihomo-.gamma.-linolenoylethanolamide
n-(8z,11z,14z-eicosatrienoyl)ethanolamine
HMS3402M13
HMS3649H13
8,11,14-eicosatrienamide,n-(2-hydroxyethyl)-,(8z,11z,14z)-
dgla ea
dihomo-gamma-linolenoylethanolamide
n-|a-linolenoylethanolamine
Q27087920
SR-01000946660-1
sr-01000946660
(8z,11z,14z)-n-(2-hydroxyethyl)-8,11,14-eicosatrienamide
dihomo- gamma -linolenylethanolamide
anandamide c20:3(8z,11z,14z)
ana(20:3)
DTXSID201199860
AKOS040756868
dihomo-??-linolenoyl ethanolamide
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
N-acylethanolamine 20:3A N-(long-chain-acyl)ethanolamine in which the acyl group contains 20 carbons and 3 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]

Protein Targets (4)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
glucocerebrosidaseHomo sapiens (human)Potency6.30960.01268.156944.6684AID2101
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency2.81841.000010.475628.1838AID1457
[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)Ki0.05320.00020.566510.0000AID238320; AID49668
Cannabinoid receptor 1Homo sapiens (human)Ki0.32570.00010.50779.6000AID49152; AID49322
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (34)

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)
[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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
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.
AID1347154Primary screen GU AMC qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID49668In vitro binding affinity was determined against rat brain Cannabinoid receptor 11997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.
AID49322Compound was evaluated for its binding affinity towards Cannabinoid receptor 1 [Inactive form(R) of CB1 receptor]2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Conformational memories and the endocannabinoid binding site at the cannabinoid CB1 receptor.
AID1616997Antiallergic activity in rat RBL2H3 cells assessed as inhibition of DNP-HSA-mediated degranulation by measuring decrease in beta-hexosaminidase activity preincubated for 30 mins followed by DNP-HSA stimulation and measured after 30 mins by 4-nitrophenyl 22019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of Fish Oil Derivatives with Antiallergic Activity in Vitro and in Vivo.
AID387968Antiproliferative activity against mouse RAW264.7 cells at 10 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation.
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.
AID49152Binding affinity against the cannabinoid receptor1997Journal of medicinal chemistry, Feb-28, Volume: 40, Issue:5
Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor.
AID387967Antiproliferative activity against human WI38 cells at 10 uM after 48 hrs relative to control2008Bioorganic & medicinal chemistry, Nov-15, Volume: 16, Issue:22
Acylamido analogs of endocannabinoids selectively inhibit cancer cell proliferation.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (33.33)18.2507
2000's3 (25.00)29.6817
2010's3 (25.00)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (8.33%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other11 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]