Page last updated: 2024-12-09

elaidic acid

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

Cross-References

ID SourceID
PubMed CID637517
CHEMBL ID460657
CHEBI ID27997
CHEBI ID36021
SCHEMBL ID1139
SCHEMBL ID6693
MeSH IDM0057776

Synonyms (94)

Synonym
LS-14685
EN300-19543
elaidinsaeure
CHEBI:27997 ,
trans-delta(9)-octadecenoic acid
(e)-octadec-9-enoic acid
NSC26988 ,
trans-.delta.9-octadecenoic acid
wln: qv8u9-t
nsc-26988
trans-.delta.(sup 9)-octadecenoic acid
trans-octadec-9-enoic acid
einecs 204-006-6
nsc 26988
ai3-15840
trans-delta(sup 9)-octadecenoic acid
9-octadecenoic acid, (9e)-
inchi=1/c18h34o2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10h,2-8,11-17h2,1h3,(h,19,20)/b10-9
(9e)-octadec-9-enoic acid
18:1, n-9
CHEBI:36021
c18:1, n-9
delta(9)-octadecenoic acid
9-trans-octadecenoic acid
trans-oleic acid
112-79-8
C01712
elaidic acid ,
(e)-oleic acid
(9e)-octadecenoic acid
trans-d9-octadecenoic acid
elaidinsaure
9-octadecenoic acid, (e)-
d9-trans-octadecenoic acid
acide elaidique
trans-9-octadecenoic acid
trans-elaidic acid
elaidic acid, >=99.0% (gc)
1FE3
DB04224
1LFO
elaidinic acid
9-elaidic acid
9e-octadecenoic acid
LMFA01030073
D89C6CAA-1C31-4C71-BD3B-EA155A22E10C
bdbm50250904
AKOS000278123
L001099
octadec-9-enoic acid anion
CHEMBL460657 ,
BMSE000643
O0010
einecs 217-977-6
delta9-octadecenoic acid
4837010h8c ,
unii-4837010h8c
S3357
CCG-35462
STL282737
SCHEMBL1139
SCHEMBL6693
elaidic acid [mi]
(e)-9-octadecenoic acid
c18:1 n-9t
9-trans-oleic acid
DTXSID8058619
9-octadecenoicacid
Q-201508
AC-33773
HMS3649H19
9-octadecenoic acid,(9e)-
J-002839
elaidic acid, analytical standard
elaidic acid, analytical sample grade
oleic_acid
Q413491
benzenebutanoic acid, 2-methyl-.alpha.,.gamma.-dioxo-, ethyl ester
SR-01000946663-1
sr-01000946663
FS-4659
HY-113016
CS-0059361
NCGC00344330-02
D78470
A905948
EN300-1697685
oleic acid (9,10-d2)
CS-0368443
oleic-13c18 acid
elaidic acid, ?99%
trans-delta9-octadecenoic acid
9-octadecaenoic acid
fatty acid 18:1 n-9 trans

Research Excerpts

Overview

Elaidic acid is a trans-fatty acid found in many food products and implicated for having potentially health hazardous effects in humans. The underlying molecular mechanisms underlying its neurotoxic effects remain largely unknown.

ExcerptReferenceRelevance
"Elaidic acid, which is a major trans fatty acid, has been reported to be involved in neurotoxicity; however, the underlying molecular mechanisms underlying its neurotoxic effects remain largely unknown. "( Elaidic acid induces cell apoptosis through induction of ROS accumulation and endoplasmic reticulum stress in SH‑SY5Y cells.
Gong, XY; Ma, WW; Wang, H; Wei, F; Xiao, R; Yu, HL; Yuan, LH; Zhao, L, 2017
)
3.34
"Elaidic acid is a trans-fatty acid found in many food products and implicated for having potentially health hazardous effects in humans. "( Phosphatidylcholine and sphingomyelin containing an elaidoyl fatty acid can form cholesterol-rich lateral domains in bilayer membranes.
Björkbom, A; Ramstedt, B; Slotte, JP, 2007
)
1.78

Treatment

ExcerptReferenceRelevance
"Elaidic acid treatment also induced or inhibited the expression of numerous ER stress/UPR‑associated molecules."( Elaidic acid induces cell apoptosis through induction of ROS accumulation and endoplasmic reticulum stress in SH‑SY5Y cells.
Gong, XY; Ma, WW; Wang, H; Wei, F; Xiao, R; Yu, HL; Yuan, LH; Zhao, L, 2017
)
2.62

Bioavailability

ExcerptReferenceRelevance
" Despite recent advances in the clinical development of azacytidine, the use of the drug is limited by its low bioavailability and dependency on variably expressed nucleoside transporters for cellular uptake."( Delivery of 5-azacytidine to human cancer cells by elaidic acid esterification increases therapeutic drug efficacy.
Brueckner, B; Fichtner, I; Hals, PA; Lyko, F; Markelova, MR; Rius, M; Sandvold, ML, 2010
)
0.61
" The oral bioavailability of the encapsulated molecules and the selective exposure of animals to each trans-fatty acid of interest were confirmed in healthy rats."( Drinkable lecithin nanovesicles to study the biological effects of individual hydrophobic macronutrients and food preferences.
Berthiaume, L; Bertrand, N; Chotard, É; Julien, P; Mohammadi, F; Rudkowska, I, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
food componentA physiological role played by any substance that is distributed in foodstuffs. It includes materials derived from plants or animals, such as vitamins or minerals, as well as environmental contaminants.
[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
octadec-9-enoic acidAn octadecenoic acid with a double bond at C-9.
[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 (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Spike glycoproteinSevere acute respiratory syndrome-related coronavirusPotency35.48130.009610.525035.4813AID1479145
[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)
DNA topoisomerase 1Homo sapiens (human)IC50 (µMol)1,000.00000.02101.862610.0000AID361445
[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)
Chain A, FATTY ACID-BINDING PROTEIN, BRAINHomo sapiens (human)Kd0.04670.04670.05000.0534AID977611
Chain A, Fatty Acid-binding Protein, BrainHomo sapiens (human)Kd0.04670.04670.05000.0534AID977611
Chain A, Liver Fatty Acid Binding ProteinRattus norvegicus (Norway rat)Kd0.20000.20000.20000.2000AID977611
Fatty acid-binding protein, adipocyteHomo sapiens (human)Kd58.00000.15000.65822.0500AID32788
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (22)

Processvia Protein(s)Taxonomy
DNA topological changeDNA topoisomerase 1Homo sapiens (human)
chromatin remodelingDNA topoisomerase 1Homo sapiens (human)
circadian rhythmDNA topoisomerase 1Homo sapiens (human)
response to xenobiotic stimulusDNA topoisomerase 1Homo sapiens (human)
programmed cell deathDNA topoisomerase 1Homo sapiens (human)
phosphorylationDNA topoisomerase 1Homo sapiens (human)
peptidyl-serine phosphorylationDNA topoisomerase 1Homo sapiens (human)
circadian regulation of gene expressionDNA topoisomerase 1Homo sapiens (human)
embryonic cleavageDNA topoisomerase 1Homo sapiens (human)
chromosome segregationDNA topoisomerase 1Homo sapiens (human)
DNA replicationDNA topoisomerase 1Homo sapiens (human)
response to bacteriumFatty acid-binding protein, adipocyteHomo sapiens (human)
long-chain fatty acid transportFatty acid-binding protein, adipocyteHomo sapiens (human)
cholesterol homeostasisFatty acid-binding protein, adipocyteHomo sapiens (human)
negative regulation of DNA-templated transcriptionFatty acid-binding protein, adipocyteHomo sapiens (human)
positive regulation of inflammatory responseFatty acid-binding protein, adipocyteHomo sapiens (human)
white fat cell differentiationFatty acid-binding protein, adipocyteHomo sapiens (human)
brown fat cell differentiationFatty acid-binding protein, adipocyteHomo sapiens (human)
cellular response to lithium ionFatty acid-binding protein, adipocyteHomo sapiens (human)
cellular response to tumor necrosis factorFatty acid-binding protein, adipocyteHomo sapiens (human)
positive regulation of cold-induced thermogenesisFatty acid-binding protein, adipocyteHomo sapiens (human)
fatty acid transportFatty acid-binding protein, adipocyteHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
RNA polymerase II cis-regulatory region sequence-specific DNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA bindingDNA topoisomerase 1Homo sapiens (human)
chromatin bindingDNA topoisomerase 1Homo sapiens (human)
double-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
single-stranded DNA bindingDNA topoisomerase 1Homo sapiens (human)
RNA bindingDNA topoisomerase 1Homo sapiens (human)
DNA topoisomerase type I (single strand cut, ATP-independent) activityDNA topoisomerase 1Homo sapiens (human)
protein serine/threonine kinase activityDNA topoisomerase 1Homo sapiens (human)
protein bindingDNA topoisomerase 1Homo sapiens (human)
ATP bindingDNA topoisomerase 1Homo sapiens (human)
DNA binding, bendingDNA topoisomerase 1Homo sapiens (human)
protein domain specific bindingDNA topoisomerase 1Homo sapiens (human)
supercoiled DNA bindingDNA topoisomerase 1Homo sapiens (human)
long-chain fatty acid transmembrane transporter activityFatty acid-binding protein, adipocyteHomo sapiens (human)
long-chain fatty acid bindingFatty acid-binding protein, adipocyteHomo sapiens (human)
hormone receptor bindingFatty acid-binding protein, adipocyteHomo sapiens (human)
fatty acid bindingFatty acid-binding protein, adipocyteHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
nuclear chromosomeDNA topoisomerase 1Homo sapiens (human)
P-bodyDNA topoisomerase 1Homo sapiens (human)
fibrillar centerDNA topoisomerase 1Homo sapiens (human)
male germ cell nucleusDNA topoisomerase 1Homo sapiens (human)
nucleusDNA topoisomerase 1Homo sapiens (human)
nucleoplasmDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
perikaryonDNA topoisomerase 1Homo sapiens (human)
protein-DNA complexDNA topoisomerase 1Homo sapiens (human)
nucleolusDNA topoisomerase 1Homo sapiens (human)
nucleusFatty acid-binding protein, adipocyteHomo sapiens (human)
cytoplasmFatty acid-binding protein, adipocyteHomo sapiens (human)
lipid dropletFatty acid-binding protein, adipocyteHomo sapiens (human)
cytosolFatty acid-binding protein, adipocyteHomo sapiens (human)
extracellular exosomeFatty acid-binding protein, adipocyteHomo sapiens (human)
cytosolFatty acid-binding protein, adipocyteHomo sapiens (human)
nucleusFatty acid-binding protein, adipocyteHomo sapiens (human)
virion membraneSpike glycoproteinSevere acute respiratory syndrome-related coronavirus
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1519392Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519398Antibacterial activity against Pseudomonas aeruginosa ATCC 15442 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519397Antibacterial activity against Escherichia coli NCTC 8196 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID32788Binding affinity against Adipocyte lipid binding protein2002Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12
Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.
AID1519393Antibacterial activity against Staphylococcus aureus ATCC 6538 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519391Antibacterial activity against Staphylococcus aureus NCTC 4163 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519399Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519395Antibacterial activity against Enterococcus hirae ATCC 10541 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID1519394Antibacterial activity against Staphylococcus epidermidis ATCC 12228 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID361445Inhibition of DNA topoisomerase 12002Journal of natural products, Nov, Volume: 65, Issue:11
Total synthesis and biological evaluation of (5Z,9Z)-5,9-hexadecadienoic acid, an inhibitor of human topoisomerase I.
AID1519396Antibacterial activity against Escherichia coli ATCC 25922 assessed as reduction in bacterial cell growth incubated for 18 hrs by two fold serial microdilution method2020European journal of medicinal chemistry, Jan-01, Volume: 185Anticancer and antimicrobial effects of novel ciprofloxacin fatty acids conjugates.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2000The Journal of biological chemistry, Sep-01, Volume: 275, Issue:35
Crystal structure and thermodynamic analysis of human brain fatty acid-binding protein.
AID1811Experimentally measured binding affinity data derived from PDB1997The Journal of biological chemistry, Mar-14, Volume: 272, Issue:11
The crystal structure of the liver fatty acid-binding protein. A complex with two bound oleates.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB1997The Journal of biological chemistry, Mar-14, Volume: 272, Issue:11
The crystal structure of the liver fatty acid-binding protein. A complex with two bound oleates.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (230)

TimeframeStudies, This Drug (%)All Drugs %
pre-199045 (19.57)18.7374
1990's47 (20.43)18.2507
2000's38 (16.52)29.6817
2010's81 (35.22)24.3611
2020's19 (8.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 54.66

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

MetricThis Compound (vs All)
Research Demand Index54.66 (24.57)
Research Supply Index5.50 (2.92)
Research Growth Index4.79 (4.65)
Search Engine Demand Index88.81 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (54.66)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials9 (3.83%)5.53%
Reviews5 (2.13%)6.00%
Case Studies1 (0.43%)4.05%
Observational0 (0.00%)0.25%
Other220 (93.62%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]