Compounds > linoleamide
Page last updated: 2024-11-11

linoleamide

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

Description

linoleamide: C18-H33-N-O [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

linoleamide : A fatty amide obtained from linoleic acid. [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 CID6435901
CHEMBL ID64122
CHEBI ID82984
SCHEMBL ID124306
SCHEMBL ID19535589
MeSH IDM0378993

Synonyms (42)

Synonym
(9z,12z)-octadeca-9,12-dienoic acid amide
bdbm50150483
octadeca-9,12-dienoic acid amide
BRD-K64044582-001-02-8
linoleamide
IDI1_033842
NCGC00161183-03
NCGC00161183-05
NCGC00161183-04
BSPBIO_001372
NCGC00161183-06
HMS1989E14
chebi:82984 ,
CHEMBL64122 ,
BML2-C09
HMS1791E14
HMS1361E14
(9z,12z)-octadeca-9,12-dienamide
9z,12z-octadecadienamide
LMFA08010008
5340s2uxsp ,
9,12-octadecadienamide, (9z,12z)-
9,12-octadecadienamide
unii-5340s2uxsp
einecs 223-644-6
linoleic acid amide
3999-01-7
(9z,12z)-octadeca-9,12-dien-1-amide
linoleamide (linoleic acid amide)
linoleamide [inci]
SCHEMBL124306
linoleoyl amide
HMS3402E14
DTXSID4042098
AS-62109
SCHEMBL19535589
linoleamide, >=98% (hplc)
linoleate amide
Q27156521
SFIHQZFZMWZOJV-HZJYTTRNSA-N
mfcd00798239
AKOS037645674

Research Excerpts

Overview

Linoleamide is an endogenous lipid that has been shown to induce sleep in cats, rats and humans.

ExcerptReferenceRelevance
"Linoleamide is an endogenous lipid that has been shown to induce sleep in cats, rats and humans. "( Linoleamide, a brain lipid that induces sleep, increases cytosolic Ca2+ levels in MDCK renal tubular cells.
Huang, JK; Jan, CR, 2001)		3.2
[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 (1)

ClassDescription
primary fatty amideA primary carboxamide RC(=O)NH2 resultng from the formal condensation of the carboxy group of a fatty acid with ammonia.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency8.91250.003245.467312,589.2998AID2517
regulator of G-protein signaling 4Homo sapiens (human)Potency23.77810.531815.435837.6858AID504845
[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)
Sterol O-acyltransferase 1Rattus norvegicus (Norway rat)IC50 (µMol)150.00000.00580.66266.0000AID241990
Sterol O-acyltransferase 1Homo sapiens (human)IC50 (µMol)49.00000.02501.79758.0000AID241602; AID241603
Transient receptor potential cation channel subfamily V member 2Rattus norvegicus (Norway rat)IC50 (µMol)1.70000.03701.93458.6000AID1400243; AID1400244
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
cholesterol metabolic processSterol O-acyltransferase 1Homo sapiens (human)
macrophage derived foam cell differentiationSterol O-acyltransferase 1Homo sapiens (human)
cholesterol storageSterol O-acyltransferase 1Homo sapiens (human)
cholesterol effluxSterol O-acyltransferase 1Homo sapiens (human)
very-low-density lipoprotein particle assemblySterol O-acyltransferase 1Homo sapiens (human)
low-density lipoprotein particle clearanceSterol O-acyltransferase 1Homo sapiens (human)
cholesterol homeostasisSterol O-acyltransferase 1Homo sapiens (human)
positive regulation of amyloid precursor protein biosynthetic processSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
fatty-acyl-CoA bindingSterol O-acyltransferase 1Homo sapiens (human)
sterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
protein bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol bindingSterol O-acyltransferase 1Homo sapiens (human)
cholesterol O-acyltransferase activitySterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
endoplasmic reticulumSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
membraneSterol O-acyltransferase 1Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID241602Inhibitory activity against human Acyl coenzyme A:cholesterol acyltransferase 12004Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16
Acyl-CoA: cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas.
AID241603Inhibitory activity against human Acyl coenzyme A:cholesterol acyltransferase 22004Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16
Acyl-CoA: cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas.
AID30888Inhibition of human macrophage acyl-CoA cholesterol acyl transferase (ACAT) at 5 oleolyl-CoA and microsomes of U937 cells1999Bioorganic & medicinal chemistry letters, Jul-19, Volume: 9, Issue:14
Polyunsaturated fatty acid anilides as inhibitors of acyl-coA: cholesterol acyltransferase (ACAT).
AID1400244Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of CBD-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
AID1400243Antagonist activity at recombinant rat TRPV2 expressed in HEK293 cells assessed as inhibition of LPC-induced Ca2+ levels preincubated for 5 mins followed by agonist addition by Fuo-4-AM based spectrofluorimetry2018Journal of medicinal chemistry, 09-27, Volume: 61, Issue:18
Elongation of the Hydrophobic Chain as a Molecular Switch: Discovery of Capsaicin Derivatives and Endogenous Lipids as Potent Transient Receptor Potential Vanilloid Channel 2 Antagonists.
AID30887Inhibition of human macrophage acyl-CoA cholesterol acyl transferase (ACAT) at 0.5 oleolyl-CoA and microsomes of U937 cells1999Bioorganic & medicinal chemistry letters, Jul-19, Volume: 9, Issue:14
Polyunsaturated fatty acid anilides as inhibitors of acyl-coA: cholesterol acyltransferase (ACAT).
AID241990Inhibitory activity against rat liver microsomal Acyl coenzyme A:cholesterol acyltransferase2004Bioorganic & medicinal chemistry letters, Aug-16, Volume: 14, Issue:16
Acyl-CoA: cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas.
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.
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.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.14)18.2507
2000's3 (21.43)29.6817
2010's8 (57.14)24.3611
2020's2 (14.29)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 35.46

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

MetricThis Compound (vs All)
Research Demand Index35.46 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.10 (4.65)
Search Engine Demand Index42.91 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (35.46)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetylcarnitine
Acetylcarnitine: An acetic acid ester of CARNITINE that facilitates movement of ACETYL COA into the matrices of mammalian MITOCHONDRIA during the oxidation of FATTY ACIDS.		3.1210O-acylcarnitinehuman metabolite
carnitine
[no description available]		2.1310amino-acid betainehuman metabolite;
mouse metabolite
ethanolamine
[no description available]		2.0710ethanolamines;
primary alcohol;
primary amine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
palmitic acid
Palmitic Acid: A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids.. hexadecanoic acid : A straight-chain, sixteen-carbon, saturated long-chain fatty acid.		2.1710long-chain fatty acid;
straight-chain saturated fatty acid		algal metabolite;
Daphnia magna metabolite;
EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor;
plant metabolite
2-aminoethoxydiphenyl borate
2-aminoethoxydiphenyl borate: is a novel membrane-penetrable modulator and transient receptor potential channel blocker; structure in first source; do not confuse with 2-APB cpd. 2-aminoethoxydiphenylborane : An organoboron compound that is diphenylborane in which the borane hydrogen is replaced by a 2-aminoethoxy group.		2.1710organoboron compound;
primary amino compound		calcium channel blocker;
IP3 receptor antagonist;
potassium channel opener
palmidrol
palmidrol: a cannabinoid receptor-inactive eCB-related molecule used as prophylactic in helping to prevent respiratory viral infection. palmitoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of palmitic (hexadecanoic) acid.		2.1710endocannabinoid;
N-(long-chain-acyl)ethanolamine;
N-(saturated fatty acyl)ethanolamine		anti-inflammatory drug;
anticonvulsant;
antihypertensive agent;
neuroprotective agent
ornithine
Ornithine: An amino acid produced in the urea cycle by the splitting off of urea from arginine.. ornithine : An alpha-amino acid that is pentanoic acid bearing two amino substituents at positions 2 and 5.		3.1210non-proteinogenic L-alpha-amino acid;
ornithine		algal metabolite;
hepatoprotective agent;
mouse metabolite
cumene hydroperoxide
cumene hydroperoxide: RN given refers to parent cpd. cumene hydroperoxide : A peroxol that is cumene in which the alpha-hydrogen is replaced by a hydroperoxy group.		2.1310peroxolenvironmental contaminant;
Mycoplasma genitalium metabolite;
oxidising agent
arachidic acid
icosanoic acid : A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.		2.1710long-chain fatty acid;
straight-chain saturated fatty acid		plant metabolite
stearoylethanolamide
N-(octadecanoyl)ethanolamine : An N-acylethanolamine 18:0 that is the ethanolamide of octadecanoic acid.		2.1710N-acylethanolamine 18:0
s-adenosylmethionine
acylcarnitine: structure in first source. S-adenosyl-L-methioninate : A sulfonium betaine that is a conjugate base of S-adenosyl-L-methionine obtained by the deprotonation of the carboxy group.		2.1310sulfonium betainehuman metabolite
fura-2
Fura-2: A fluorescent calcium chelating agent which is used to study intracellular calcium in tissues.		210
hexadecanamide
hexadecanamide : A fatty amide that is the carboxamide derived from palmitic acid.		2.5220primary fatty amidemetabolite
pd 128042
PD 128042: structure given in first source		210anilide
arachidonic acid
icosa-5,8,11,14-tetraenoic acid : Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.. arachidonate : A long-chain fatty acid anion resulting from the removal of a proton from the carboxy group of arachidonic acid.		2.1710icosa-5,8,11,14-tetraenoic acid;
long-chain fatty acid;
omega-6 fatty acid		Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
human metabolite;
mouse metabolite
oleic acid
Oleic Acid: An unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed). oleic acid : An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry.		2.4720octadec-9-enoic acidantioxidant;
Daphnia galeata metabolite;
EC 3.1.1.1 (carboxylesterase) inhibitor;
Escherichia coli metabolite;
mouse metabolite;
plant metabolite;
solvent
sphingosine
sphing-4-enine : A sphingenine in which the C=C double bond is located at the 4-position.. sphingenine : A 2-aminooctadecene-1,3-diol having (2S,3R)-configuration.. sphingoid : Sphinganine, its homologs and stereoisomers, and the hydroxy and unsaturated derivatives of these compounds.. 2-aminooctadec-4-ene-1,3-diol : A 2-aminooctadecene-1,3-diol having its double bond at position 4.		3.1210sphing-4-eninehuman metabolite;
mouse metabolite
linoleic acid
Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.		2.0210octadecadienoic acid;
omega-6 fatty acid		algal metabolite;
Daphnia galeata metabolite;
plant metabolite
erucic acid
[no description available]		2.1710docosenoic acid
anandamide
anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.		2.1710endocannabinoid;
N-acylethanolamine 20:4		human blood serum metabolite;
neurotransmitter;
vasodilator agent
oleylamide
oleylamide: plastic additive; can cause contact urticaria; RN given refers to (Z)-isomer; a sleep inducing factor. aliphatic amide : A carboxamide in which the amide linkage is bonded directly to an aliphatic system.. oleamide : A fatty amide derived from oleic acid.		2.9640primary fatty amidehuman metabolite;
plant metabolite
linoleoyl ethanolamide
linoleoyl ethanolamide: RN given for (Z,Z)-isomer. linoleoyl ethanolamide : An N-acylethanolamine 18:2 that is the ethanolamide of linoleic acid.		2.1710N-acylethanolamine 18:2EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor
N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine
synaptamide: structurally similar to the endocannabinoid N-arachidonoylethanolamine (anandamide). N-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoylethanolamine : An N-acylethanolamine 22:6 that is the ethanolamide of (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid.		2.1710endocannabinoid;
N-acylethanolamine 22:6
n-oleoylethanolamine
N-oleoylethanolamine: ceramidase inhibitor. oleoyl ethanolamide : An N-(long-chain-acyl)ethanolamine that is the ethanolamide of oleic acid. The monounsaturated analogue of the endocannabinoid anandamide.		2.1710endocannabinoid;
N-(long-chain-acyl)ethanolamine;
N-acylethanolamine 18:1		EC 3.5.1.23 (ceramidase) inhibitor;
geroprotector;
PPARalpha agonist
olvanil
[no description available]		2.1710methoxybenzenes;
phenols
oleoylanilide
oleoylanilide: alters lipid metabolism of lung & adipose tissue; do not confuse with oleoanilide; RN given refers to (Z)-isomer. oleylanilide : The fatty amide resulting from the formal condensation of oleic acid and aniline.		2.0210anilide;
fatty amide
erucyl amide
erucyl amide: RN given refers to (Z)-isomer. erucamide : A primary fatty amide resulting from the formal condensation of the carboxy group of erucic acid with ammonia. It is commonly used as a slip additive in the plastic manufacturing industry.		2.171013-docosenamideEC 3.1.1.7 (acetylcholinesterase) inhibitor;
human metabolite;
mammalian metabolite;
plant metabolite;
rat metabolite
n-(2-methylbenzyl)linoleamide
N-(2-methylbenzyl)linoleamide: RN given refers to (Z,Z)-isomer; structure		210organic molecular entity
ConditionIndicatedRelationship StrengthStudiesTrials
Encephalitis, Polio
[description not available]		02.0610
Poliomyelitis
An acute infectious disease of humans, particularly children, caused by any of three serotypes of human poliovirus (POLIOVIRUS). Usually the infection is limited to the gastrointestinal tract and nasopharynx, and is often asymptomatic. The central nervous system, primarily the spinal cord, may be affected, leading to rapidly progressive paralysis, coarse FASCICULATION and hyporeflexia. Motor neurons are primarily affected. Encephalitis may also occur. The virus replicates in the nervous system, and may cause significant neuronal loss, most notably in the spinal cord. A rare related condition, nonpoliovirus poliomyelitis, may result from infections with nonpoliovirus enteroviruses. (From Adams et al., Principles of Neurology, 6th ed, pp764-5)		02.0610
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.2510
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Diabetes Mellitus, Adult-Onset
[description not available]		03.1210
Innate Inflammatory Response
[description not available]		03.1210
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		03.1210
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		03.1210
B-Cell Chronic Lymphocytic Leukemia
[description not available]		02.1310
Leukemia, Lymphocytic, Chronic, B-Cell
A chronic leukemia characterized by abnormal B-lymphocytes and often generalized lymphadenopathy. In patients presenting predominately with blood and bone marrow involvement it is called chronic lymphocytic leukemia (CLL); in those predominately with enlarged lymph nodes it is called small lymphocytic lymphoma. These terms represent spectrums of the same disease.		02.1310
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.0710