Page last updated: 2024-11-10

7,10,13,16-docosatetraenylethanolamide

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

Description

7,10,13,16-docosatetraenylethanolamide: found in brain; binds to the cannabinoid receptor; structure given in first source; RN given refers to (ALL-Z)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5282273
CHEMBL ID321585
CHEBI ID34478
SCHEMBL ID6259736
MeSH IDM0222431

Synonyms (49)

Synonym
BRD-K30199352-001-02-9
BSPBIO_001535
IDI1_034005
NCGC00161197-03
NCGC00161197-05
NCGC00161197-04
NCGC00161197-06
7,10,13,16-docosatetraenoylethanolamine
n-(7z,10z,13z,16z-docosatetraenoyl)-ethanolamine
NCGC00161197-07
HMS1989M17
docosatetra-7z,10z,13z,16z-enoyl ethanolamide
CHEMBL321585 ,
chebi:34478 ,
BML2-C01
anandamide (22:4,n-6)
HMS1361M17
HMS1791M17
adrenoyl-ethanolamine
adrenoyl-ea
LMFA08040047
(7z,10z,13z,16z)-n-(2-hydroxyethyl)docosa-7,10,13,16-tetraenamide
150314-35-5
7,10,13,16-docosatetraenylethanolamide
7,10,13,16-dtea
7,10,13,16-docosatetraenamide, n-(2-hydroxyethyl)-, (all-z)-
n-(2-hydroxyethyl)-7,10,13,16-docosatetraenamide (all-z)-
anandamide + pmsf
bdbm85675
gtpl5445
n-docosatetra-7,10,13,16-enoylethanolamine
n-(2-hydroxyethyl)7z,10z,13z,16z-docosatetraenamide
FMVHVRYFQIXOAF-DOFZRALJSA-N
n-(2-hydroxyethyl)-7z,10z,13z,16z-docosatetraenamide
SCHEMBL6259736
AKOS024456629
HMS3649L17
HMS3402M17
nae(22:4)
adrenoyl ethanolamide
docosa-7,10,13,16-tetraenoic acid (2-hydroxy-ethyl)-amide
n-(7z,10z,13z,16z-docosatetraenoyl)-ethanolamide
docosa-7,10,13,16-tetraenoate
Q5287253
SR-01000946675-1
sr-01000946675
(7z,10z,13z,16z)-n-(2-hydroxyethyl)-7,10,13,16-docosatetraenamide
7,10,13,16-docosatetraenamide, n-(2-hydroxyethyl)-, (7z,10z,13z,16z)-
DTXSID501028460
[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 22:4A N-(long-chain-acyl)ethanolamine in which the acyl group contains 22 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]

Protein Targets (18)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency35.48130.003245.467312,589.2998AID2517
Chain A, TYROSYL-DNA PHOSPHODIESTERASEHomo sapiens (human)Potency39.81070.004023.8416100.0000AID485290
Chain A, Ferritin light chainEquus caballus (horse)Potency25.11895.623417.292931.6228AID485281
phosphopantetheinyl transferaseBacillus subtilisPotency57.12200.141337.9142100.0000AID1490
Microtubule-associated protein tauHomo sapiens (human)Potency39.81070.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency29.39690.011212.4002100.0000AID1030
glucocerebrosidaseHomo sapiens (human)Potency31.62280.01268.156944.6684AID2101
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency12.58930.035520.977089.1251AID504332
Bloom syndrome protein isoform 1Homo sapiens (human)Potency28.18380.540617.639296.1227AID2528
polyunsaturated fatty acid lipoxygenase ALOX12Homo sapiens (human)Potency39.81071.000012.232631.6228AID1452
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency35.48130.354828.065989.1251AID504847
DNA polymerase kappa isoform 1Homo sapiens (human)Potency39.81070.031622.3146100.0000AID588579
[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)Ki0.03420.00020.566510.0000AID238320; AID49668
Cannabinoid receptor 1Homo sapiens (human)Ki0.03440.00010.50779.6000AID49322
Cannabinoid receptor 1Mus musculus (house mouse)Ki0.03440.00060.72467.2000AID48996
Cannabinoid receptor 2Mus musculus (house mouse)Ki0.03440.00020.07970.7943AID48996
[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)
Potassium channel subfamily K member 2Homo sapiens (human)EC50 (µMol)5.10000.18702.72248.1800AID1802150
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (45)

Processvia Protein(s)Taxonomy
cardiac ventricle developmentPotassium channel subfamily K member 2Homo sapiens (human)
G protein-coupled receptor signaling pathwayPotassium channel subfamily K member 2Homo sapiens (human)
memoryPotassium channel subfamily K member 2Homo sapiens (human)
response to mechanical stimulusPotassium channel subfamily K member 2Homo sapiens (human)
response to axon injuryPotassium channel subfamily K member 2Homo sapiens (human)
negative regulation of cardiac muscle cell proliferationPotassium channel subfamily K member 2Homo sapiens (human)
cellular response to hypoxiaPotassium channel subfamily K member 2Homo sapiens (human)
potassium ion transmembrane transportPotassium channel subfamily K member 2Homo sapiens (human)
cochlea developmentPotassium channel subfamily K member 2Homo sapiens (human)
positive regulation of cellular response to hypoxiaPotassium channel subfamily K member 2Homo sapiens (human)
negative regulation of DNA biosynthetic processPotassium channel subfamily K member 2Homo sapiens (human)
stabilization of membrane potentialPotassium channel subfamily K member 2Homo 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
outward rectifier potassium channel activityPotassium channel subfamily K member 2Homo sapiens (human)
potassium ion leak channel activityPotassium channel subfamily K member 2Homo 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membranePotassium channel subfamily K member 2Homo sapiens (human)
plasma membranePotassium channel subfamily K member 2Homo sapiens (human)
cell surfacePotassium channel subfamily K member 2Homo sapiens (human)
apical plasma membranePotassium channel subfamily K member 2Homo sapiens (human)
neuronal cell bodyPotassium channel subfamily K member 2Homo sapiens (human)
calyx of HeldPotassium channel subfamily K member 2Homo sapiens (human)
astrocyte projectionPotassium channel subfamily K member 2Homo sapiens (human)
voltage-gated potassium channel complexPotassium channel subfamily K member 2Homo sapiens (human)
plasma membranePotassium channel subfamily K member 2Homo 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
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.
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.
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.
AID48996Ability to displace [3H]HU-243 binding to cannabinoid receptor in synaptosomal membrane1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
Two new unsaturated fatty acid ethanolamides in brain that bind to the 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.
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.
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.
AID1802150TREK1 Assay from Article 10.1111/cbdd.12810: \\Identification of the first in silico-designed TREK1 antagonists that block channel currents dose dependently.\\2016Chemical biology & drug design, Dec, Volume: 88, Issue:6
Identification of the first in silico-designed TREK1 antagonists that block channel currents dose dependently.
[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's3 (25.00)18.2507
2000's3 (25.00)29.6817
2010's4 (33.33)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.08

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 Index12.08 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.64 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.08)

All Compounds (24.57)

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]