Page last updated: 2024-12-11

virodhamine

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

Description

virodhamine: arachidonic acid and ethanolamine joined by an ester linkage, like anandamide with oxygen and nitrogen reversed; an endocannabinoid from rat; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5712057
CHEMBL ID187349
CHEBI ID183424
SCHEMBL ID395796
MeSH IDM0427329

Synonyms (29)

Synonym
NCGC00162430-02
NCGC00162430-01
virodhamine
o-arachidonoyl ethanolamine
o-aea
2-aminoethyl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate
CHEMBL187349 ,
bdbm50171285
(5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoic acid 2-amino-ethyl ester
287937-12-6
CHEBI:183424
2-aminoethyl-5z,8z,11z,14z-eicosatetraenoate
LMFA00000014
o-arachidonoylethanolamine
gtpl5554
SCHEMBL395796
(2-aminoethyl) 5z,8z,11z,14z-eicosatetraen ester
DLHLOYYQQGSXCC-DOFZRALJSA-N
arachidonic acid (2-aminoethyl) ester
AKOS024456673
o-(2-aminoethyl)-5z,8z,11z,14z-eicosatetraenoate
arachidonic acid-(2-aminoethyl)-ester
Q4463
DTXSID601018179
F82263
MS-25351
5,8,11,14-eicosatetraenoic acid, 2-aminoethyl ester, (5z,8z,11z,14z)-
CS-0065429
HY-116418

Research Excerpts

Overview

Virodhamine is a recently identified novel endocannabinoid.

ExcerptReferenceRelevance
"Virodhamine is a recently identified novel endocannabinoid. "( Vasorelaxant activities of the putative endocannabinoid virodhamine in rat isolated small mesenteric artery.
Hiley, CR; Ho, WS, 2004
)
2.01
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
fatty acid esterA carboxylic ester in which the carboxylic acid component can be any fatty acid.
[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 (12)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Ferritin light chainEquus caballus (horse)Potency22.38725.623417.292931.6228AID485281
phosphopantetheinyl transferaseBacillus subtilisPotency39.47230.141337.9142100.0000AID1490
Microtubule-associated protein tauHomo sapiens (human)Potency39.81070.180013.557439.8107AID1460
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency3.16230.011212.4002100.0000AID1030
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency14.12540.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency50.11870.354828.065989.1251AID504847
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency70.79460.010039.53711,122.0200AID1479
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency25.11890.00798.23321,122.0200AID2546
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)Ki1.90000.00020.566510.0000AID238320
Cannabinoid receptor 1Homo sapiens (human)Ki0.91200.00010.50779.6000AID1127511
Cannabinoid receptor 2Rattus norvegicus (Norway rat)Ki0.91200.02000.22060.9120AID1127511
[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 (4)

Assay IDTitleYearJournalArticle
AID238321Binding affinity for cannabinoid receptor 22005Journal of medicinal chemistry, Aug-11, Volume: 48, Issue:16
The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.
AID1127511Displacement of [3H]-CP55940 from human CB1 receptor by liquid scintillation counting in presence of serine protease inhibitor PMSF2013Journal 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.
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 (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's13 (59.09)29.6817
2010's8 (36.36)24.3611
2020's1 (4.55)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.65

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 Index24.65 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.65)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (18.18%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other18 (81.82%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]