11-octadecenoic acid profile

11-octadecenoic acid, also known as **vaccenic acid**, is a monounsaturated fatty acid (MUFA) with the chemical formula CH₃(CH₂)₅CH=CH(CH₂)₉COOH. It's naturally found in dairy products, meat, and some plant oils.

**Here's why it's important for research:**

* **Cardiovascular Health:** Vaccenic acid is a precursor to **oleic acid**, a heart-healthy MUFA found in olive oil. Studies suggest that vaccenic acid can lower LDL (bad) cholesterol and increase HDL (good) cholesterol, potentially contributing to better cardiovascular health.
* **Metabolic Health:** Research indicates that vaccenic acid might play a role in regulating blood sugar levels and insulin sensitivity, making it potentially beneficial for individuals with type 2 diabetes.
* **Inflammation and Immunity:** Vaccenic acid demonstrates anti-inflammatory properties, possibly due to its ability to modulate immune cell responses. This is relevant for research into chronic inflammatory diseases.
* **Cancer Research:** Some studies suggest that vaccenic acid might have anticancer properties, particularly in the context of colon cancer. However, more research is needed to confirm these effects.
* **Animal Nutrition:** In animal feed, vaccenic acid is important for promoting milk production and improving milk quality in dairy cows.

**Overall, vaccenic acid is an interesting fatty acid with potential health benefits. Ongoing research is exploring its role in various physiological processes, including:**

* **Lipid metabolism**
* **Cellular signaling**
* **Gene expression**

**Further research on vaccenic acid may lead to new insights into the prevention and treatment of various diseases, as well as the development of novel nutritional strategies.**

11-octadecenoic acid: vaccenic acid is the (E)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trans-vaccenic acid : The trans- isomer of vaccenic 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]

ID Source	ID
PubMed CID	5281127
CHEBI ID	28727
CHEBI ID	36023
SCHEMBL ID	38907
SCHEMBL ID	38908
MeSH ID	M0143969

Synonym
trans-octadec-11-enoic acid
(11e)-octadec-11-enoic acid
18:1 trans-11
octadec-11(e)-enoic acid
TVA ,
c18:1 trans-11
11(e)-vaccenic acid
CHEBI:28727
trans-vaccenic acid
11-octadecenoic acid, (e)-
CHEBI:36023
18:1 (n-7)
octadec-11-ensaeure
c18:1 (n-7)
delta(11)-octadecensaeure
11-octadecenoic acid
octadec-11-enoic acid
c18:1 (11)
693-72-1
trans-11-octadecenoic acid
(11e)-octadecenoic acid
C08367
trans-vaccenic acid, >=99% (capillary gc)
11e-octadecenoic acid
LMFA01030077
11-octadecenoyl alcohol
F1779992-4E48-4116-9E7B-004DEF567B15
11-octadecen-1-ol, (z)-
cis-vaccenoyl alcohol
(e)-octadec-11-enoic acid
143-25-9
ai3-36458
einecs 211-758-9
gq72ogu4ev ,
unii-gq72ogu4ev
AKOS015892938
11-trans-octadecenoic acid
vaccenic acid [who-dd]
18:1e(n-7)
vaccenic acid [mi]
SCHEMBL38907
SCHEMBL38908
11-octadecenoic acid, (11e)-
UWHZIFQPPBDJPM-BQYQJAHWSA-N
mfcd00002734
11z-octadecenoate
(11z)-octadecenoic acid
octadec-11-enoicacid
11-aoctadecenoic acid
A866854
Q419047
HY-113427
CS-0059470
F82236
DTXSID301009341
AS-57528
trans-11-octadecenoicacid

Excerpt	Reference	Relevance
" Both fats were well tolerated, and no adverse events or mortality were observed during the treatment nor after a 2-week observation period."	( A 4-week repeated oral dose toxicity study of dairy fat naturally enriched in vaccenic, rumenic and α-linolenic acids in rats. Anadon, A; Ares, I; de la Fuente, MA; Gomez-Cortes, P; Juarez, M; Martinez, MA; Martinez-Larranaga, MR; Ramos, E, 2011)	0.37

Excerpt	Reference	Relevance
"Twenty cows were used in a randomized block design experiment for 6 wk to determine the influence of feeding partial ruminally inert Ca salts of palm and fish oil (Ca-PFO), alone or in combination with extruded full-fat soybeans or soybean oil, on milk fatty acid (FA) methyl esters composition and consumer acceptability of milk and Cheddar cheese."	( Milk and cheese from cows fed calcium salts of palm and fish oil alone or in combination with soybean products. Allred, SL; Brennand, CP; Dhiman, TR; Khanal, RC; Luchini, ND; McMahon, DJ, 2006)	0.33

Excerpt	Reference	Relevance
" The objective of this study was to assess the intestinal bioavailability of various VA sources including synthetic free fatty acid (FFA) and natural ruminant triglyceride forms, as well as the mechanistic pathways that mediate VA's bioactivity."	( The intestinal bioavailability of vaccenic acid and activation of peroxisome proliferator-activated receptor-α and -γ in a rodent model of dyslipidemia and the metabolic syndrome. Anderson, HD; Dugan, ME; Field, CJ; Jacome-Sosa, MM; Lu, Y; Proctor, SD; Reaney, MJ; Ruth, MR; Scott, SL; Shen, J; Vine, DF; Wang, Y, 2012)	0.38
"Although there is extensive information describing the positive biological effects of conjugated linoleic acid and its main isomer rumenic acid (RA; C18:2 cis 9, trans 11), and alpha-linolenic acid (ALA) and vaccenic acid (TVA), data about their bioavailability are not available."	( Oral Absorption and Disposition of alpha-Linolenic, Rumenic and Vaccenic Acids After Administration as a Naturally Enriched Goat Dairy Fat to Rats. Anadón, A; Ares, I; Castellano, V; Fontecha, J; Juarez, M; Martínez, MA; Martínez-Larrañaga, MR; Rodríguez-Alcalá, LM, 2015)	0.42
" 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

Excerpt	Relevance	Reference
" As expected, small increases in dietary CLA at the low end of the CLA dose-response range did not reduce tumorigenesis."	( cis-9, trans-11 CLA derived endogenously from trans-11 18:1 reduces cancer risk in rats. Barbano, DM; Bauman, DE; Corl, BA; Ip, C, 2003)	0.32

Class	Description
vaccenic acid	An octadecenoic acid having a double bond at position 11; and which can occur in cis- or trans- configurations.
[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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	12 (5.71)	18.7374
1990's	8 (3.81)	18.2507
2000's	85 (40.48)	29.6817
2010's	93 (44.29)	24.3611
2020's	12 (5.71)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	13 (6.07%)	5.53%
Reviews	7 (3.27%)	6.00%
Case Studies	1 (0.47%)	4.05%
Observational	0 (0.00%)	0.25%
Other	193 (90.19%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
carnitine [no description available]	2	1	0	amino-acid betaine	human metabolite; mouse metabolite
methane Methane: The simplest saturated hydrocarbon. It is a colorless, flammable gas, slightly soluble in water. It is one of the chief constituents of natural gas and is formed in the decomposition of organic matter. (Grant & Hackh's Chemical Dictionary, 5th ed). methane : A one-carbon compound in which the carbon is attached by single bonds to four hydrogen atoms. It is a colourless, odourless, non-toxic but flammable gas (b.p. -161degreeC).	2.07	1	0	alkane; gas molecular entity; mononuclear parent hydride; one-carbon compound	bacterial metabolite; fossil fuel; greenhouse gas
3-hydroxybutyric acid 3-Hydroxybutyric Acid: BUTYRIC ACID substituted in the beta or 3 position. It is one of the ketone bodies produced in the liver.. 3-hydroxybutyric acid : A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. Also used to synthesise biodegradable plastics.	3.41	1	1	(omega-1)-hydroxy fatty acid; 3-hydroxy monocarboxylic acid; hydroxybutyric acid	human metabolite
malic acid malic acid : A 2-hydroxydicarboxylic acid that is succinic acid in which one of the hydrogens attached to a carbon is replaced by a hydroxy group.. 2-hydroxydicarboxylic acid : Any dicarboxylic acid carrying a hydroxy group on the carbon atom at position alpha to the carboxy group.	2.04	1	0	2-hydroxydicarboxylic acid; C4-dicarboxylic acid	food acidity regulator; fundamental metabolite
lactic acid Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.	7.13	1	0	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna 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.	2.75	3	0	long-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
phenol [no description available]	2.17	1	0	phenols	antiseptic drug; disinfectant; human xenobiotic metabolite; mouse metabolite
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2.05	1	0	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
stearic acid octadecanoic acid : A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.	3.41	7	0	long-chain fatty acid; saturated fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; human metabolite; plant metabolite
sucrose Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.	2.43	2	0	glycosyl glycoside	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; osmolyte; Saccharomyces cerevisiae metabolite; sweetening agent
leucine Leucine: An essential branched-chain amino acid important for hemoglobin formation.. leucine : A branched-chain amino acid that consists of glycine in which one of the hydrogens attached to the alpha-carbon is substituted by an isobutyl group.	2	1	0	amino acid zwitterion; L-alpha-amino acid; leucine; proteinogenic amino acid; pyruvate family amino acid	algal metabolite; Escherichia coli metabolite; human metabolite; mouse metabolite; plant metabolite; Saccharomyces cerevisiae metabolite
acrylic acid acrylic acid: RN given refers to parent cpd. acrylic acid : A alpha,beta-unsaturated monocarboxylic acid that is ethene substituted by a carboxy group.	2.08	1	0	alpha,beta-unsaturated monocarboxylic acid	metabolite
nitroblue tetrazolium Nitroblue Tetrazolium: Colorless to yellow dye that is reducible to blue or black formazan crystals by certain cells; formerly used to distinguish between nonbacterial and bacterial diseases, the latter causing neutrophils to reduce the dye; used to confirm diagnosis of chronic granulomatous disease.	2.05	1	0	organic cation
margaric acid margaric acid: RN given refers to unlabeled parent cpd. heptadecanoic acid : A C17 saturated fatty acid and trace component of fats in ruminants.	2.05	1	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; mammalian metabolite
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.	2.17	1	0	long-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
cellobiose beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue.	2.03	1	0	cellobiose	epitope
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.13	1	0	dialdehyde	biomarker
sterculic acid sterculic acid: structure. sterculic acid : A long-chain, monounsaturated fatty acid composed of 9-octadecenoic acid having a 9,10-cyclopropenyl group.	2.08	1	0	cyclopropenyl fatty acid; long-chain fatty acid; monounsaturated fatty acid
pentadecanoic acid pentadecanoic acid: in serum as a marker for intake of milk fat. pentadecanoic acid : A straight-chain saturated fatty acid containing fifteen-carbon atoms.	2.49	2	0	long-chain fatty acid; straight-chain saturated fatty acid	algal metabolite; Daphnia magna metabolite; food component; human blood serum metabolite; plant metabolite
undecane undecane : A straight-chain alkane with 11 carbon atoms.	2.25	1	0	alkane
d-alpha tocopherol Vitamin E: A generic descriptor for all TOCOPHEROLS and TOCOTRIENOLS that exhibit ALPHA-TOCOPHEROL activity. By virtue of the phenolic hydrogen on the 2H-1-benzopyran-6-ol nucleus, these compounds exhibit varying degree of antioxidant activity, depending on the site and number of methyl groups and the type of ISOPRENOIDS.. tocopherol : A collective name for a group of closely related lipids that contain a chroman-6-ol nucleus substituted at position 2 by a methyl group and by a saturated hydrocarbon chain consisting of three isoprenoid units. They are designated as alpha-, beta-, gamma-, and delta-tocopherol depending on the number and position of additional methyl substituents on the aromatic ring. Tocopherols occur in vegetable oils and vegetable oil products, almost exclusively with R,R,R configuration. Tocotrienols differ from tocopherols only in having three double bonds in the hydrocarbon chain.. vitamin E : Any member of a group of fat-soluble chromanols that exhibit biological activity against vitamin E deficiency. The vitamers in this class consists of a chroman-6-ol core which is substituted at position 2 by a methyl group and (also at position 2) either a saturated or a triply-unsaturated hydrocarbon chain consisting of three isoprenoid units. The major function of vitamin E is to act as a natural antioxidant by scavenging free radicals and molecular oxygen.. (R,R,R)-alpha-tocopherol : An alpha-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of alpha-tocopherol, it is found particularly in sunflower and olive oils.	3.84	3	0	alpha-tocopherol	algal metabolite; antiatherogenic agent; anticoagulant; antioxidant; antiviral agent; EC 2.7.11.13 (protein kinase C) inhibitor; immunomodulator; micronutrient; nutraceutical; plant metabolite
cadmium Cadmium: An element with atomic symbol Cd, atomic number 48, and atomic weight 112.41. It is a metal and ingestion will lead to CADMIUM POISONING.. elemental cadmium : An element in the zinc group of the periodic table with atomic number 48, atomic mass 112, M.P. 321degreeC, and B.P. 765degreeC). An odourless, tasteless, and highly poisonous soft, ductile, lustrous metal with electropositive properties. It has eight stable isotopes: (106)Cd, (108)Cd,(110)Cd, (111)Cd, (112)Cd, (113)Cd, (114)Cd and (116)Cd, with (112)Cd and (114)Cd being the most common.	2.17	1	0	cadmium molecular entity; zinc group element atom
acetylglucosamine Acetylglucosamine: The N-acetyl derivative of glucosamine.. N-acetyl-beta-D-glucosamine : An N-acetyl-D-glucosamine having beta-configuration at the anomeric centre.	1.99	1	0	N-acetyl-D-glucosamine	epitope
deuterium Deuterium: The stable isotope of hydrogen. It has one neutron and one proton in the nucleus.	7.38	2	0	dihydrogen
galactose aldohexose : A hexose with a (potential) aldehyde group at one end.	2.06	1	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	1	0	sulfonium betaine	human metabolite
rosiglitazone [no description available]	2.05	1	0	aminopyridine; thiazolidinediones	EC 6.2.1.3 (long-chain-fatty-acid--CoA ligase) inhibitor; ferroptosis inhibitor; insulin-sensitizing drug
homocysteine Homocysteine: A thiol-containing amino acid formed by a demethylation of METHIONINE.. homocysteine : A sulfur-containing amino acid consisting of a glycine core with a 2-mercaptoethyl side-chain.. L-homocysteine : A homocysteine that has L configuration.	2.15	1	0	amino acid zwitterion; homocysteine; serine family amino acid	fundamental metabolite; mouse metabolite
singlet oxygen Singlet Oxygen: An excited state of molecular oxygen generated photochemically or chemically. Singlet oxygen reacts with a variety of biological molecules such as NUCLEIC ACIDS; PROTEINS; and LIPIDS; causing oxidative damages.	2.13	1	0	chalcogen; monoatomic oxygen; nonmetal atom	macronutrient
biotin vitamin B7 : Any member of a group of vitamers that belong to the chemical structural class called biotins that exhibit biological activity against vitamin B7 deficiency. Vitamin B7 deficiency is very rare in individuals who take a normal balanced diet. Foods rich in biotin are egg yolk, liver, cereals, vegetables (spinach, mushrooms) and rice. Symptoms associated with vitamin B7 deficiency include thinning hair, scaly skin rashes around eyes, nose and mouth, and brittle nails. The vitamers include biotin and its ionized and salt forms.	1.92	1	0	biotins; vitamin B7	coenzyme; cofactor; Escherichia coli metabolite; fundamental metabolite; human metabolite; mouse metabolite; nutraceutical; prosthetic group; Saccharomyces cerevisiae metabolite
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	2.05	1	0
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.21	1	0	cyclodextrin
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.	2.71	3	0	icosa-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
palmitoleic acid hexadecenoate : A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.	5.78	10	2	hexadec-9-enoic acid	algal metabolite; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; human blood serum 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.	6.01	34	0	octadec-9-enoic acid	antioxidant; Daphnia galeata metabolite; EC 3.1.1.1 (carboxylesterase) inhibitor; Escherichia coli metabolite; mouse metabolite; plant metabolite; solvent
tacrolimus Tacrolimus: A macrolide isolated from the culture broth of a strain of Streptomyces tsukubaensis that has strong immunosuppressive activity in vivo and prevents the activation of T-lymphocytes in response to antigenic or mitogenic stimulation in vitro.. tacrolimus (anhydrous) : A macrolide lactam containing a 23-membered lactone ring, originally isolated from the fermentation broth of a Japanese soil sample that contained the bacteria Streptomyces tsukubaensis.	2.13	1	0	macrolide lactam	bacterial metabolite; immunosuppressive agent
eicosapentaenoic acid icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.	4.52	5	1	icosapentaenoic acid; omega-3 fatty acid	anticholesteremic drug; antidepressant; antineoplastic agent; Daphnia galeata metabolite; fungal metabolite; micronutrient; mouse metabolite; nutraceutical
alpha-asarone asarone: structure in Merck Index, 9th ed, #847. asarone : A phenylpropanoid that is benzene substituted by methoxy groups at positions 1, 2 and 4 and a propen-1-yl group at position 5. It has been isolated from Acorus.. alpha-asarone : The trans-isomer of asarone.	2.08	1	0	asarone	anticonvulsant; GABA modulator
elaidic acid [no description available]	5.94	31	0	octadec-9-enoic acid	food component
sesquiterpenes [no description available]	2.08	1	0
quinine [no description available]	1.96	1	0	cinchona alkaloid	antimalarial; muscle relaxant; non-narcotic analgesic
ovalbumin Ovalbumin: An albumin obtained from the white of eggs. It is a member of the serpin superfamily.	2.06	1	0
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.25	1	0	prostaglandins E	human metabolite; mouse metabolite; oxytocic
dinoprost Dinoprost: A naturally occurring prostaglandin that has oxytocic, luteolytic, and abortifacient activities. Due to its vasocontractile properties, the compound has a variety of other biological actions.. prostaglandin F2alpha : A prostaglandins Falpha that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9, 11 and 15. It is a naturally occurring prostaglandin used to induce labor.	2.92	1	0	monocarboxylic acid; prostaglandins Falpha	human 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.	13.86	34	2	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
beta carotene beta Carotene: A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC).. provitamin A : A provitamin that can be converted into vitamin A by enzymes from animal tissues.	3.15	1	0	carotenoid beta-end derivative; cyclic carotene	antioxidant; biological pigment; cofactor; ferroptosis inhibitor; human metabolite; mouse metabolite; plant metabolite; provitamin A
8,11,14-eicosatrienoic acid 8,11,14-Eicosatrienoic Acid: A 20-carbon-chain fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid, 5,8,11,14-eicosatetraenoic acid, only at position 5.. all-cis-icosa-8,11,14-trienoic acid : An icosatrienoic acid having three cis double bonds at positions 8, 11 and 14.	2	1	0	fatty acid 20:3; long-chain fatty acid	fungal metabolite; human metabolite; nutraceutical
rumenic acid 9-cis,11-trans-octadecadienoic acid : An octadeca-9,11-dienoic acid having 9-cis,11-trans-stereochemistry.	7.13	12	3	octadeca-9,11-dienoic acid
gamma-linolenic acid gamma-Linolenic Acid: An omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed). gamma-linolenic acid : A C18, omega-6 acid fatty acid comprising a linolenic acid having cis- double bonds at positions 6, 9 and 12.	2	1	0	linolenic acid; omega-6 fatty acid	human metabolite; mouse metabolite; plant metabolite
alpha-linolenic acid linolenic acid : A two-membered subclass of octadecatrienoic acid comprising the (9Z,12Z,15Z)- and (6Z,9Z,12Z)-isomers. Linolenic acids are nutrients essential to the formation of prostaglandins and are also used in making paints and synthetic resins.. linolenate : A polyunsaturated fatty acid anion obtained by deprotonation of the carboxy group of either alpha- or gamma-linolenic acid.	4.08	14	0	linolenic acid; omega-3 fatty acid	micronutrient; mouse metabolite; nutraceutical
petroselinic acid petroselinic acid: isomer of oleic acid in parsley seeds; RN given refers to cpd without isomeric designation; NM refers to (Z)-isomer; structure in Merck Index, 9th ed, #6974. petroselinic acid : The cis-isomer of octadec-6-enoic acid, a long-chain fatty acid.	2.01	1	0	octadec-6-enoic acid	plant metabolite
soraphen a [no description available]	2.08	1	0	cyclic hemiketal; ether; macrolide; olefinic compound	bacterial metabolite; EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor; teratogenic agent
anandamide anandamide : An N-acylethanolamine 20:4 resulting from the formal condensation of carboxy group of arachidonic acid with the amino group of ethanolamine.	3.04	1	0	endocannabinoid; N-acylethanolamine 20:4	human blood serum metabolite; neurotransmitter; vasodilator agent
cerulenin Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.	2.02	1	0	epoxide; monocarboxylic acid amide	antifungal agent; antiinfective agent; antilipemic drug; antimetabolite; antimicrobial agent; fatty acid synthesis inhibitor
8-epi-prostaglandin f2alpha 8-epi-prostaglandin F2alpha: a potent preglomerular vasoconstrictor acting principally through thromboxane A2 receptor activation. 8-epi-prostaglandin F2alpha : An isoprostane that is prostaglandin F2alpha having inverted stereochemistry at the 8-position.	2.92	1	0	F2-isoprostane	biomarker; bronchoconstrictor agent; vasoconstrictor agent
cis-vaccenic acid cis-vaccenic acid: isomer of oleic acid. vaccenic acid : An octadecenoic acid having a double bond at position 11; and which can occur in cis- or trans- configurations.. cis-vaccenic acid : The cis isomer of vaccenic acid.	2.63	3	0	vaccenic acid
9,11-linoleic acid 9,11-linoleic acid: a conjugated dienoic linoleate (CLA); RN given refers to cpd without isomeric designation in Chemline. (9E,11E)-octadecadienoic acid : An octadeca-9,11-dienoic acid having 9-trans,11-trans-stereochemistry.	10.04	32	3	octadeca-9,11-dienoic acid	anti-inflammatory agent; antiatherogenic agent; antineoplastic agent; apoptosis inducer; bacterial xenobiotic metabolite; human metabolite
caryophyllene caryophyllene: RN given refers to cpd without isomeric designation; structure given in first source	2.08	1	0
diphenylhexatriene Diphenylhexatriene: A fluorescent compound that emits light only in specific configurations in certain lipid media. It is used as a tool in the study of membrane lipids.	1.96	1	0	alkatriene	fluorochrome
triolein Triolein: (Z)-9-Octadecenoic acid 1,2,3-propanetriyl ester.. triolein : A triglyceride formed by esterification of the three hydroxy groups of glycerol with oleic acid. Triolein is one of the two components of Lorenzo's oil.	2.05	1	0	triglyceride	Caenorhabditis elegans metabolite; plant metabolite
tannins Tannins: Polyphenolic compounds with molecular weights of around 500-3000 daltons and containing enough hydroxyl groups (1-2 per 100 MW) for effective cross linking of other compounds (ASTRINGENTS). The two main types are HYDROLYZABLE TANNINS and CONDENSED TANNINS. Historically, the term has applied to many compounds and plant extracts able to render skin COLLAGEN impervious to degradation. The word tannin derives from the Celtic word for OAK TREE which was used for leather processing.	2.07	1	0
phosphatidylcholines Phosphatidylcholines: Derivatives of PHOSPHATIDIC ACIDS in which the phosphoric acid is bound in ester linkage to a CHOLINE moiety.	2.44	2	0	1,2-diacyl-sn-glycero-3-phosphocholine
glycolipids [no description available]	2.06	1	0
natriuretic peptide, brain Natriuretic Peptide, Brain: A PEPTIDE that is secreted by the BRAIN and the HEART ATRIA, stored mainly in cardiac ventricular MYOCARDIUM. It can cause NATRIURESIS; DIURESIS; VASODILATION; and inhibits secretion of RENIN and ALDOSTERONE. It improves heart function. It contains 32 AMINO ACIDS.	2.06	1	0	polypeptide
flavin mononucleotide Flavin Mononucleotide: A coenzyme for a number of oxidative enzymes including NADH DEHYDROGENASE. It is the principal form in which RIBOFLAVIN is found in cells and tissues.	2.13	1	0

Condition	Relationship Strength	Studies	Trials
Innate Inflammatory Response [description not available]	4.12	5	0
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.	4.12	5	0
Benign Neoplasms [description not available]	4.69	4	0
Neoplasms New abnormal growth of tissue. Malignant neoplasms show a greater degree of anaplasia and have the properties of invasion and metastasis, compared to benign neoplasms.	4.69	4	0
Cardiometabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components not only include metabolic dysfunctions of METABOLIC SYNDROME but also HYPERTENSION, and ABDOMINAL OBESITY.	4.25	6	0
Diabetes Mellitus, Adult-Onset [description not available]	2.58	2	0
Insulin Sensitivity [description not available]	3.59	8	0
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.	2.58	2	0
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	3.59	8	0
Metabolic Syndrome A cluster of symptoms that are risk factors for CARDIOVASCULAR DISEASES and TYPE 2 DIABETES MELLITUS. The major components of metabolic syndrome include ABDOMINAL OBESITY; atherogenic DYSLIPIDEMIA; HYPERTENSION; HYPERGLYCEMIA; INSULIN RESISTANCE; a proinflammatory state; and a prothrombotic (THROMBOSIS) state.	4.25	6	0
Pregnancy The status during which female mammals carry their developing young (EMBRYOS or FETUSES) in utero before birth, beginning from FERTILIZATION to BIRTH.	4.76	6	1
Allergic Rhinitis [description not available]	3.12	1	0
Asthma, Bronchial [description not available]	3.12	1	0
Dermatitis, Eczematous [description not available]	3.12	1	0
Allergic Reaction [description not available]	3.41	2	0
Asthma A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).	3.12	1	0
Eczema A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).	3.12	1	0
Hypersensitivity Altered reactivity to an antigen, which can result in pathologic reactions upon subsequent exposure to that particular antigen.	3.41	2	0
Rhinitis, Allergic An inflammation of the NASAL MUCOSA triggered by ALLERGENS.	3.12	1	0
Cardiovascular Diseases Pathological conditions involving the CARDIOVASCULAR SYSTEM including the HEART; the BLOOD VESSELS; or the PERICARDIUM.	7.35	6	1
Diabetes Mellitus A heterogeneous group of disorders characterized by HYPERGLYCEMIA and GLUCOSE INTOLERANCE.	2.17	1	0
Parodontosis [description not available]	2.17	1	0
Periodontal Diseases Pathological processes involving the PERIODONTIUM including the gum (GINGIVA), the alveolar bone (ALVEOLAR PROCESS), the DENTAL CEMENTUM, and the PERIODONTAL LIGAMENT.	2.17	1	0
Necrosis The death of cells in an organ or tissue due to disease, injury or failure of the blood supply.	2.21	1	0
Cancer of Nasopharynx [description not available]	2.21	1	0
Nasopharyngeal Neoplasms Tumors or cancer of the NASOPHARYNX.	2.21	1	0
Depression Depressive states usually of moderate intensity in contrast with MAJOR DEPRESSIVE DISORDER present in neurotic and psychotic disorders.	2.21	1	0
Obesity A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).	5.15	10	1
Weight Gain Increase in BODY WEIGHT over existing weight.	4.53	5	1
Adenocarcinoma, Basal Cell [description not available]	2.1	1	0
Breast Cancer [description not available]	2.1	1	0
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.1	1	0
Breast Neoplasms Tumors or cancer of the human BREAST.	2.1	1	0
Disease Exacerbation [description not available]	2.48	2	0
Fatty Liver, Nonalcoholic [description not available]	2.5	2	0
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	4.99	5	0
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	2.5	2	0
Eczema, Atopic [description not available]	2.1	1	0
Airway Hyper-Responsiveness [description not available]	2.1	1	0
Breathing Sounds [description not available]	2.1	1	0
Delayed Effects, Prenatal Exposure [description not available]	2.51	2	0
Dermatitis, Atopic A chronic inflammatory genetically determined disease of the skin marked by increased ability to form reagin (IgE), with increased susceptibility to allergic rhinitis and asthma, and hereditary disposition to a lowered threshold for pruritus. It is manifested by lichenification, excoriation, and crusting, mainly on the flexural surfaces of the elbow and knee. In infants it is known as infantile eczema.	2.1	1	0
Respiratory Sounds Noises, normal and abnormal, heard on auscultation over any part of the RESPIRATORY TRACT.	2.1	1	0
Alloxan Diabetes [description not available]	2.52	2	0
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.28	6	0
Cancer of Colon [description not available]	2.13	1	0
Colonic Neoplasms Tumors or cancer of the COLON.	2.13	1	0
Elevated Cholesterol [description not available]	4.41	1	1
Hypercholesterolemia A condition with abnormally high levels of CHOLESTEROL in the blood. It is defined as a cholesterol value exceeding the 95th percentile for the population.	4.41	1	1
Hypertriglyceridemia A condition of elevated levels of TRIGLYCERIDES in the blood.	4.41	1	1
Complications, Pregnancy [description not available]	2.11	1	0
Intertrochanteric Fractures [description not available]	2.13	1	0
Hip Fractures Fractures of the FEMUR HEAD; the FEMUR NECK; (FEMORAL NECK FRACTURES); the trochanters; or the inter- or subtrochanteric region. Excludes fractures of the acetabulum and fractures of the femoral shaft below the subtrochanteric region (FEMORAL FRACTURES).	2.13	1	0
Cardiac Diseases [description not available]	2.96	1	0
Heart Diseases Pathological conditions involving the HEART including its structural and functional abnormalities.	2.96	1	0
Allergic Contact Dermatitis [description not available]	2.06	1	0
Dermatitis, Allergic Contact A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.	2.06	1	0
Chronic Illness [description not available]	2.06	1	0
Cardiac Failure [description not available]	2.06	1	0
Chronic Disease Diseases which have one or more of the following characteristics: they are permanent, leave residual disability, are caused by nonreversible pathological alteration, require special training of the patient for rehabilitation, or may be expected to require a long period of supervision, observation, or care (Dictionary of Health Services Management, 2d ed). For epidemiological studies chronic disease often includes HEART DISEASES; STROKE; CANCER; and diabetes (DIABETES MELLITUS, TYPE 2).	2.06	1	0
Heart Failure A heterogeneous condition in which the heart is unable to pump out sufficient blood to meet the metabolic need of the body. Heart failure can be caused by structural defects, functional abnormalities (VENTRICULAR DYSFUNCTION), or a sudden overload beyond its capacity. Chronic heart failure is more common than acute heart failure which results from sudden insult to cardiac function, such as MYOCARDIAL INFARCTION.	2.06	1	0
Overweight A status with BODY WEIGHT that is above certain standards. In the scale of BODY MASS INDEX, overweight is defined as having a BMI of 25.0-29.9 kg/m2. Overweight may or may not be due to increases in body fat (ADIPOSE TISSUE), hence overweight does not equal over fat.	4.37	1	1
Adipocere [description not available]	2.07	1	0
Dyslipidemia [description not available]	2.46	2	0
Dyslipidemias Abnormalities in the serum levels of LIPIDS, including overproduction or deficiency. Abnormal serum lipid profiles may include high total CHOLESTEROL, high TRIGLYCERIDES, low HIGH DENSITY LIPOPROTEIN CHOLESTEROL, and elevated LOW DENSITY LIPOPROTEIN CHOLESTEROL.	2.46	2	0
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.07	1	0
Compensatory Hyperinsulinemia A GLUCOSE-induced HYPERINSULINEMIA, a marker of insulin-resistant state. It is a mechanism to compensate for reduced sensitivity to insulin.	2.07	1	0
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.07	1	0
Hyperinsulinism A syndrome with excessively high INSULIN levels in the BLOOD. It may cause HYPOGLYCEMIA. Etiology of hyperinsulinism varies, including hypersecretion of a beta cell tumor (INSULINOMA); autoantibodies against insulin (INSULIN ANTIBODIES); defective insulin receptor (INSULIN RESISTANCE); or overuse of exogenous insulin or HYPOGLYCEMIC AGENTS.	2.07	1	0
Impaired Glucose Tolerance [description not available]	2.08	1	0
Glucose Intolerance A pathological state in which BLOOD GLUCOSE level is less than approximately 140 mg/100 ml of PLASMA at fasting, and above approximately 200 mg/100 ml plasma at 30-, 60-, or 90-minute during a GLUCOSE TOLERANCE TEST. This condition is seen frequently in DIABETES MELLITUS, but also occurs with other diseases and MALNUTRITION.	2.08	1	0
Blood Pressure, High [description not available]	2.08	1	0
Weight Reduction [description not available]	3.84	2	1
Hypertension Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.	2.08	1	0
Weight Loss Decrease in existing BODY WEIGHT.	3.84	2	1
Arteriosclerosis Thickening and loss of elasticity of the walls of ARTERIES of all sizes. There are many forms classified by the types of lesions and arteries involved, such as ATHEROSCLEROSIS with fatty lesions in the ARTERIAL INTIMA of medium and large muscular arteries.	2.93	1	0
Experimental Mammary Neoplasms [description not available]	2.41	2	0
Animal Mammary Carcinoma [description not available]	2.02	1	0
Heart Disease, Ischemic [description not available]	4.33	1	1
Myocardial Ischemia A disorder of cardiac function caused by insufficient blood flow to the muscle tissue of the heart. The decreased blood flow may be due to narrowing of the coronary arteries (CORONARY ARTERY DISEASE), to obstruction by a thrombus (CORONARY THROMBOSIS), or less commonly, to diffuse narrowing of arterioles and other small vessels within the heart. Severe interruption of the blood supply to the myocardial tissue may result in necrosis of cardiac muscle (MYOCARDIAL INFARCTION).	4.33	1	1
Obstructive Lung Diseases [description not available]	2.04	1	0
Lung Diseases, Obstructive Any disorder marked by obstruction of conducting airways of the lung. AIRWAY OBSTRUCTION may be acute, chronic, intermittent, or persistent.	2.04	1	0
Coronary Heart Disease [description not available]	2.4	2	0
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	2.4	2	0
Chronic Hepatitis C [description not available]	2	1	0
Hepatitis C, Chronic INFLAMMATION of the LIVER in humans that is caused by HEPATITIS C VIRUS lasting six months or more. Chronic hepatitis C can lead to LIVER CIRRHOSIS.	2	1	0
Lipid Metabolism, Inborn Error [description not available]	2	1	0
Condition, Preneoplastic [description not available]	2	1	0
Precancerous Conditions Pathological conditions that tend eventually to become malignant.	2	1	0

11-octadecenoic acid

Description

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Synonyms (57)

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Dosage Studied

Drug Classes (1)

Research

Studies (210)

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Research Demand Index: 28.29

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