Page last updated: 2024-12-11

oleoylanilide

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

Description

oleoylanilide: alters lipid metabolism of lung & adipose tissue; do not confuse with oleoanilide; RN given refers to (Z)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

oleylanilide : The fatty amide resulting from the formal condensation of oleic acid and aniline. [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 CID5354590
CHEMBL ID15611
CHEBI ID53721
SCHEMBL ID4143902
MeSH IDM0116418

Synonyms (42)

Synonym
oleilanilide
bdbm50147178
(z)-octadec-9-enoic acid phenylamide
(z)-n-phenyl-9-octadeceneamide
oleyl anilide
brn 3533033
nsc 14233
einecs 226-584-9
oleic acid anilide
9-octadecenamide, n-phenyl-, (z)-
oleoylanilide
oleylanilide
oleanilide
cis-9-octadecenanilide
5429-85-6
nsc-14233
nsc14233
CHEMBL15611 ,
octadec-9-enoic acid phenylamide
(z)-n-phenyloctadec-9-enamide
(9z)-n-phenyloctadec-9-enamide
(z)-n-phenyl-9-octadecenamide
CHEBI:53721 ,
unii-6j8g54zuq5
2-12-00-00150 (beilstein handbook reference)
6j8g54zuq5 ,
EPITOPE ID:117134
SCHEMBL4143902
(9z)-n-phenyl-9-octadecenamide #
YPUOCYKJOLQYQS-KTKRTIGZSA-N
oleic anilide
n-phenyl-9z-octadecenamide
HMS3649L14
AKOS027282752
Q27124174
SR-01000946736-1
sr-01000946736
n- phenyl- 9z- octadecenamide
(9z)-n-phenyl-9-octadecenamide
9-octadecenamide, n-phenyl-, (9z)-
n-phenyloleamide
DTXSID401031579

Research Excerpts

Treatment

ExcerptReferenceRelevance
"Oleoylanilide treatment causes two kinds of phenomena: alteration of the actin cytoskeleton, creating a brush-like protrusion of actin at the periphery of the cells, and reduction of the adhesiveness of these cells to laminin and fibronectin, two of the main components of the extracellular matrix in the central nervous system."( Oleoylanilide, a possible causative agent of toxic oil syndrome, interferes with the cytoskeleton in a neuronal cell line.
Behrens, MM; Martínez, JL; Moratilla, C; Renart, J,
)
2.3

Dosage Studied

ExcerptRelevanceReference
" This activity level coincided with the AchE level observed at the onset of signs in animals dosed with OPs."( Study of delayed neurotoxicity caused by fatty acid anilides in hens.
Blasco, R; Moreno, E; Repetto, M; Sanz, P, 1990
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
anilideAny aromatic amide obtained by acylation of aniline.
fatty amideA monocarboxylic acid amide derived from a 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 (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sterol O-acyltransferase 1Rattus norvegicus (Norway rat)IC50 (µMol)0.02000.00580.66266.0000AID241990
Sterol O-acyltransferase 2Homo sapiens (human)IC50 (µMol)0.17000.11003.20369.2000AID276035; AID31681
Sterol O-acyltransferase 1Homo sapiens (human)IC50 (µMol)0.14750.02501.79758.0000AID241602; AID241603; AID276034; AID31527
Acyl-CoA:cholesterol acyltransferase Oryctolagus cuniculus (rabbit)IC50 (µMol)26.00000.00600.98467.6000AID31210
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (9)

Processvia Protein(s)Taxonomy
cholesterol metabolic processSterol O-acyltransferase 2Homo sapiens (human)
macrophage derived foam cell differentiationSterol O-acyltransferase 2Homo sapiens (human)
cholesterol storageSterol O-acyltransferase 2Homo sapiens (human)
intestinal cholesterol absorptionSterol O-acyltransferase 2Homo sapiens (human)
cholesterol effluxSterol O-acyltransferase 2Homo sapiens (human)
very-low-density lipoprotein particle assemblySterol O-acyltransferase 2Homo sapiens (human)
low-density lipoprotein particle clearanceSterol O-acyltransferase 2Homo sapiens (human)
cholesterol homeostasisSterol O-acyltransferase 2Homo sapiens (human)
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 (6)

Processvia Protein(s)Taxonomy
fatty-acyl-CoA bindingSterol O-acyltransferase 2Homo sapiens (human)
sterol O-acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
protein bindingSterol O-acyltransferase 2Homo sapiens (human)
cholesterol bindingSterol O-acyltransferase 2Homo sapiens (human)
acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
cholesterol O-acyltransferase activitySterol O-acyltransferase 2Homo sapiens (human)
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 (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulumSterol O-acyltransferase 2Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 2Homo sapiens (human)
brush borderSterol O-acyltransferase 2Homo sapiens (human)
endoplasmic reticulum membraneSterol O-acyltransferase 2Homo sapiens (human)
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
AID1852775Stimulation of human 20S proteasome assessed as increase in proteasome activity at 25 uM and measured upto 60 mins using FRET peptide as substrate by FRET assay relative to control2022RSC medicinal chemistry, Sep-21, Volume: 13, Issue:9
Oleic amide derivatives as small molecule stimulators of the human proteasome's core particle.
AID31527Concentration required to inhibit Acyl coenzyme A:cholesterol acyltransferase 12004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
Human ACAT-1 and -2 inhibitory activities of saucerneol B, manassantin A and B isolated from Saururus chinensis.
AID196759Inhibition of rat glial cell gap junction at the concentration of 50 uM1999Bioorganic & medicinal chemistry letters, Apr-19, Volume: 9, Issue:8
Arachidonic acid amide inhibitors of gap junction cell-cell communication.
AID31210In vitro inhibition of acyl coenzyme A:cholesterol acyltransferase, in intestinal microsomes isolated from cholesterol-fed rabbits1992Journal of medicinal chemistry, May-01, Volume: 35, Issue:9
Inhibitors of acyl-CoA:cholesterol acyltransferase. 1. Identification and structure-activity relationships of a novel series of fatty acid anilide hypocholesterolemic agents.
AID377003Inhibition of human ACAT1 at 0.3 mM2006Journal of natural products, May, Volume: 69, Issue:5
Phenolic compounds from the roots of Lindera fruticosa.
AID276035Inhibition of human ACAT2 expressed in Hi5 cells2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata.
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.
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.
AID31681Concentration required to inhibit Acyl coenzyme A:cholesterol acyltransferase 22004Bioorganic & medicinal chemistry letters, Jun-21, Volume: 14, Issue:12
Human ACAT-1 and -2 inhibitory activities of saucerneol B, manassantin A and B isolated from Saururus chinensis.
AID276034Inhibition of human ACAT1 expressed in Hi5 cells2006Bioorganic & medicinal chemistry letters, Nov-01, Volume: 16, Issue:21
Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (33)

TimeframeStudies, This Drug (%)All Drugs %
pre-19907 (21.21)18.7374
1990's18 (54.55)18.2507
2000's7 (21.21)29.6817
2010's0 (0.00)24.3611
2020's1 (3.03)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.95

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 Index10.95 (24.57)
Research Supply Index3.58 (2.92)
Research Growth Index4.53 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.95)

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%
Other35 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]