Classification Term: 1753
Very long-chain fatty acids (ontology term: CHEMONTID:0002950)
Fatty acids with an aliphatic tail that contains at least 22 carbon atoms." []
found 99 associated metabolites at category metabolite taxonomy ontology rank level.
Ancestor: Fatty acids and conjugates
Child Taxonomies: There is no child term of current ontology term.
Nervonic acid
Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID:16394593). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID:8072429). (15Z)-tetracosenoic acid is a tetracosenoic acid having a cis-double bond at position 15. It is a conjugate acid of a (15Z)-tetracosenoate. Nervonic acid is a natural product found in Tropaeolum speciosum, Calophyllum inophyllum, and other organisms with data available. Nervonic Acid is a monounsaturated fatty acid with a 24-carbon backbone and the sole double bond originating from the 9th carbon from the methyl end, with this bond in the cis- configuration. See also: Borage Seed Oil (part of). A tetracosenoic acid having a cis-double bond at position 15. Present in fish and rape seed oils Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin. Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin.
Erucic acid
Before genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil from rapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would get stripped out of the genome as well, greatly reducing its valuable erucic acid content. Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability. Later trials showed that rats had the same problems with other vegetable fatty acids, because rats are poor at metabolising some fats. The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that of its competitors.; Erucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid.; Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ?-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50\\% of their oils. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.; The name erucic means: of or pertaining to eruca; which is a genus of flowering plants in the family Brassicaceae. It is also the Latin for coleworth, which today is better known as kale. Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. It is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. For industrial purposes, a High-Erucic Acid Rapeseed (HEAR) has been developed. These cultivars can yield 40\\% to 60\\% of the total oil recovered as erucic acid. Erucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Erucic acid’s ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:Ln9) and erucic acid (22:1N9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. Human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2\\% erucic acid by weight in the US and 5\\% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. napus and B. rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid. Erucic acid is a docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers. It is a conjugate acid of an erucate. Erucic acid is a natural product found in Dipteryx lacunifera, Myrtus communis, and other organisms with data available. Erucic Acid is a monounsaturated very long-chain fatty acid with a 22-carbon backbone and a single double bond originating from the 9th position from the methyl end, with the double bond in the cis- configuration. See also: Cod Liver Oil (part of). A docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers.
Octacosanoic acid
Octacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID:2474624). Octacosanoic acid is a higher aliphatic primary acids purified from sugar-cane (Saccharum officinarum L.) wax that has been shown to inhibit platelet aggregation induced ex vivo by addition of agonists to platelet-rich plasma (PRP) of rats, guinea pigs, and healthy human volunteers. (PMID:5099499). Octacosanoic acid is formed from octacosanol via beta-oxidation. (PMID:15847942). Octacosanoic acid is a straight-chain saturated fatty acid that is octacosane in which one of the terminal methyl groups has been oxidised to the corresponding carboxy group. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and an ultra-long-chain fatty acid. It is a conjugate acid of an octacosanoate. Octacosanoic acid is a natural product found in Lysimachia patungensis, Rhizophora apiculata, and other organisms with data available. A straight-chain saturated fatty acid that is octacosane in which one of the terminal methyl groups has been oxidised to the corresponding carboxy group. Octacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID: 2474624)
Docosanedioic acid
Phellogenic acid, also known as 1,20-eicosanedicarboxylic acid or 1,22-docosanedioate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, phellogenic acid is considered to be a fatty acid lipid molecule. Phellogenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Phellogenic acid can be found in potato, which makes phellogenic acid a potential biomarker for the consumption of this food product. Docosanedioic acid is an alpha,omega-dicarboxylic acid that is docosane in which the methyl groups have been oxidised to the corresponding carboxylic acids. It has a role as a metabolite. It is an alpha,omega-dicarboxylic acid and a dicarboxylic fatty acid. It is a conjugate acid of a docosanedioate(2-). It derives from a hydride of a docosane. Docosanedioic acid is a natural product found in Pinus radiata with data available.
Lignoceric acid (C24)
Lignoceric acid, also known as N-tetracosanoic acid or tetraeicosanoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, lignoceric acid is considered to be a fatty acid lipid molecule. Lignoceric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lignoceric acid can be found in a number of food items such as hazelnut, cheese, rye bread, and cetacea (dolphin, porpoise, whale), which makes lignoceric acid a potential biomarker for the consumption of these food products. Lignoceric acid can be found primarily in blood and feces, as well as in human fibroblasts tissue. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. In humans, lignoceric acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1\\\\% – 2.2\\\\%). This fatty acid is also a byproduct of lignin production . Tetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound. Acquisition and generation of the data is financially supported in part by CREST/JST. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2]. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2].
Docosahexaenoic acid
Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis- double bonds with the first double bond located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease (Wikipedia). Docosahexaenoic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Extensively marketed as a dietary supplement in Japan [DFC]. Doconexent is found in many foods, some of which are mung bean, fruit preserve, northern pike, and snapper. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundantly present brain and retina. It can be obtained directly from fish oil and maternal milk.
Adrenic acid
Adrenic acid, also known as 7,10,13,16-docosatetraenoic acid or adrenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Adrenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Adrenic acid can be found in blood and in human myelin tissue. Within the cell, adrenic acid is primarily located in the cytoplasm, in the membrane (predicted from logP), and in the peroxisome. It can also be found in the extracellular space. In humans, adrenic acid is involved in alpha-linolenic acid and linoleic acid metabolism. Docosatetraenoic acid designates any straight chain 22:4 fatty acid. In particular, all-cis-7,10,13,16-docosatetraenoic acid is an ω-6 fatty acid with the trivial name adrenic acid (AdA). This is a naturally occurring polyunsaturated fatty acid formed through a 2-carbon chain elongation of arachidonic acid. It is one of the most abundant fatty acids in the early human brain. This unsaturated fatty acid is also metabolized by cells into biologically active products, such as dihomoprostaglandins and dihomo-epoxyeicosatrienoic acids (dihomo-EETs) (Wikipedia). Adrenic acid, which is a prostacyclin inhibitor, appears to be a potential prothrombotic agent (PMID: 1642692). Adrenic acid, which is a prostacyclin inhibitor, appears to be potential prothrombotic agent. (PMID 1642692) [HMDB]
Docosatrienoate (22:3n3)
Docosatrienoic acid, also known as docosatrienoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosatrienoic acid is a very hydrophobic molecule, is practically insoluble (in water), and is relatively neutral. Application of docosatrienoic acid was shown to dose-dependently decrease the peak K+ current amplitude and accelerate the potassium activation and inactivation kinetics at all membrane potentials.
Docosapentaenoate (DPA; 22:5n-3)
Docosapentaenoic acid (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source. There are three functions of docosapentaenoic acid. The most important is as part of phospholipids in all animal cellular membranes: a deficiency of docosapentaenoic acid leads to faulty membranes being formed. A second is in the transport and oxidation of cholesterol: clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes: sudden failure of growth, lesions of skin and kidney and connective tissue, erythrocyte fragility, impaired fertility, uncoupling of oxidation and phosphorylation. In man pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common on Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid. (PMID: 6469703) [HMDB]. 7Z,10Z,13Z,16Z,19Z-Docosapentaenoic acid is found in many foods, some of which are green zucchini, green bell pepper, green bean, and red bell pepper. Docosapentaenoic acid (22n-3) (also known as clupanodonic acid) is an essential omega-3 fatty acid (EFA) which is prevalent in fish oils. Docosapentaenoic acid, commonly called DPA, is an intermediary between eicosapentaenoic acid (EPA, 20:5 ω-3) and docosahexaenoic acid (DHA, 22:6 ω-3). Seal oil is a rich source of this metabolite. There are three functions of docosapentaenoic acid. Most importantly, it is a component of phospholipids found in all animal cell membranes, and a deficiency of docosapentaenoic acid leads to faulty membranes being formed. Secondly, it is involved in the transport and oxidation of cholesterol, and clupanodonic acid tends to lower plasma cholesterol. A third function is as a precursor of prostanoids which are only formed from docosapentaenoic acid. Deficiency of this in experimental animals causes lesions mainly attributable to faulty cellular membranes. Outcomes include sudden failure of growth, lesions of the skin, kidney, and connective tissue, erythrocyte fragility, impaired fertility, and the uncoupling of oxidation and phosphorylation. In humans, pure deficiency of docosapentaenoic acid has been studied particularly in persons fed intravenously. A relative deficiency (that is, a low ratio in the body of docosapentaenoic to long-chain saturated fatty acids and isomers of docosapentaenoate) is common in Western diets and plays an important part in the causation of atherosclerosis, coronary thrombosis, multiple sclerosis, the triopathy of diabetes mellitus, hypertension, and certain forms of malignant disease. Various factors affect the dietary requirement of docosapentaenoic acid (PMID: 6469703). Docosapentaenoic acid (22n-3) is a component of phospholipids found in all animal cell membranes.
Behenic acid
Behenic acid, also known as docosanoate or 1-docosanoic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, behenic acid is considered to be a fatty acid lipid molecule. Behenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Behenic acid can be found in a number of food items such as rice, opium poppy, pepper (c. frutescens), and gram bean, which makes behenic acid a potential biomarker for the consumption of these food products. Behenic acid can be found primarily in blood, feces, and urine. Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 °C and boiling point of 306 °C . Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. It is an important constituent of the behen oil extracted from the seeds of the Ben-oil tree, and it is so named from the Persian month Bahman when the roots of this tree were harvested. Behenic acid has been identified in the human placenta (PMID:32033212). Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.
Resolvin D1
Resolvin D1 (RvD1) is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225).
Resolvin D2
Resolvin D2 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225) [HMDB] Resolvin D2 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225).
Nonanoyl-CoA
Nonanoyl CoA is an acyl-CoA with the C-9 fatty acid Acyl chain moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine. Nonanoyl coA is a acyl-CoA with the C-9 fatty acid Acyl chain moiety.
Diadenosine triphosphate
Diadenosine triphosphate (AP3A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP3A accumulates in cells in response to various physiological factors. AP3A FHIT (Fragile histidine Triad) is a human tumor suppressor gene. The Fhit protein is believed to inhibit tumor growth by inducing apoptosis through interaction with AP3A. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 9187362, 16401072, 12833632, 11896678). Diadenosine triphosphate (AP3A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are Ap3A, Ap4A, Ap5A, and Ap6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP3A is a primer for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. AP3A is synthesized in cells by tryptophanyl-tRNA synthetase (WRS); cellular level of AP3A significantly increases after interferon treatment. AP3A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP3A accumulates in cells in response to various physiological factors.
Docosadienoate (22:2n6)
(13Z,16Z)-Docosadienoic acid, also known as docosadienoate or C22:2N-6,9, belongs to the class of organic compounds known as very-long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. (13Z,16Z)-Docosadienoic acid is a very hydrophobic molecule that is practically insoluble (in water) and is relatively neutral. (13Z,16Z)-Docosadienoic acid can be found in feces.
Ximenic acid
Ximenic acid is found in fats and oils. Ximenic acid is isolated from seed fat of Ximenia species and fish oil lipids. Isolated from seed fat of Ximenia subspecies and fish oil lipids. Ximenic acid is found in fats and oils and fishes.
Cerebronic acid
Constituent of various glycosphingolipids of wheat, corn and other plant subspecies Cerebronic acid is found in peanut and cereals and cereal products. D-Cerebronic acid is found in mushrooms. D-Cerebronic acid is isolated from Polyporus umbellatus (zhu ling).
22-Hydroxydocosanoic acid
22-hydroxydocosanoic acid, also known as omega-hydroxybehenic acid or phellonic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, 22-hydroxydocosanoic acid is considered to be a fatty acid lipid molecule. 22-hydroxydocosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 22-hydroxydocosanoic acid can be found in potato, which makes 22-hydroxydocosanoic acid a potential biomarker for the consumption of this food product.
Hexacosanoic acid
Hexacosanoic acid, also known as N-hexacosanoate or c26:0, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, hexacosanoic acid is considered to be a fatty acid lipid molecule. Hexacosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hexacosanoic acid can be found in a number of food items such as dandelion, potato, cottonseed, and sugar apple, which makes hexacosanoic acid a potential biomarker for the consumption of these food products. Hexacosanoic acid can be found primarily in blood, as well as in human adrenal gland and fibroblasts tissues. Hexacosanoic acid exists in all eukaryotes, ranging from yeast to humans. In humans, hexacosanoic acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Hexacosanoic acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Moreover, hexacosanoic acid is found to be associated with adrenomyeloneuropathy, peroxisomal biogenesis defect, and adrenoleukodystrophy, neonatal. Hexacosanoic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. [In the chem box it is shown folded only because of lack of space. In fact, it is a straight-chain, saturated fatty acid.] . Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary treatment is with Lorenzos oil. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Adrenal insufficiency in ALD patients can be successfully treated (T3DB). Hexacosanoic acid, or cerotic acid, is a 26-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax, and is a white crystalline solid. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. Hexacosanoic acid, also known as C26:0 or N-hexacosanoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Hexacosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hexacosanoic acid is a potentially toxic compound.
(all-Z)-7,10,13-Docosatrienoic acid
(all-Z)-7,10,13-Docosatrienoic acid is a metabolite of Oleic acid produced particularly under conditions of essential fatty acid deficienc Metabolite of Oleic acid production particularly under conditions of essential fatty acid deficiency.
Pentacosanoic acid
Pentacosanoic acid, also known as pentacosanoate or hyenate, is a straight-chain saturated fatty acid and a very long-chain fatty acid. It is a conjugate acid of a pentacosanoate. Pentacosanoic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Pentacosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Pentacosanoic acid is a potentially toxic compound. Pentacosanoic acid is a straight-chain saturated fatty acid and a very long-chain fatty acid. It is a conjugate acid of a pentacosanoate. Pentacosanoic acid is a natural product found in Staphisagria macrosperma, Rhizophora apiculata, and other organisms with data available. Isolated from Citrus bergamia (bergamot orange) Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1]. Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1].
Docosapentaenoate (DPA; 22:5n-6)
Docosapentaenoic acid is an unsaturated fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans. Docosapentaenoic acid (22n-6) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Docosapentaenoic acid (22n-6) can be found in blood and urine, as well as in human adipose tissue, fibroblasts, and platelet tissues. Within the cell, docosapentaenoic acid (22n-6) is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. In humans, docosapentaenoic acid (22n-6) is involved in alpha-linolenic acid and linoleic acid metabolism. Docosapentaenoic acid (22n-6) is found to be associated with thyroid cancer. fatty acids, Unsaturated
17(R)-HDHA
Docosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761). This fatty acyl belongs to the main class of docosanoids. (Lipid Maps). Docosahexaenoic acid (DHA) is a omega-3 essential fatty acid that reduces the incidence and severity of a number of diseases. Recently, a novel series of DHA-derived lipid mediators with potent protective actions has been identified. In this study we demonstrate that dietary amplification of these DHA-derived products protects the liver from necroinflammatory injury. In vitro, supplementation of hepatocytes with DHA significantly reduced hydrogen peroxide-induced DNA damage, evaluated by the "comet assay," and oxidative stress, determined by measurement of malondialdehyde levels. In vivo, dietary supplementation of mice with DHA ameliorated carbon tetrachloride-induced necroinflammatory damage. In addition, hepatic cyclooxygenase-2 expression and PGE2 levels were significantly reduced in mice fed DHA-enriched diets. In these animals, increased hepatic formation of DHA-derived lipid mediators (i.e., 17S-hydroxy-DHA (17S-HDHA) and protectin D1) was detected by HPLC-gas chromatography/mass spectrometry analysis. Consistent with these findings, synthetic 17-HDHA abrogated genotoxic and oxidative damage in hepatocytes and decreased TNF-alpha release and 5-lipoxygenase expression in macrophages. In a transactivation assay, 17-HDHA acted in a concentration-dependent manner as a PPARgamma agonist. Taken together, these findings identify a potential role for DHA-derived products, specifically 17S-HDHA and protectin D1, in mediating the protective effects of dietary DHA in necroinflammatory liver injury. (PMID: 17056761)
20-HDoHE
20-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 20-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)
4-HDoHE
4-HDoHE is an endogenous oxidized unsaturated fatty acids. Human and mouse plasma samples also catalyzed 4-HDoHE lactonization and 5-HETE lactone hydrolysis. (PMID: 12963475) 4-HDoHE is a hydroxydocosahexaenoic acid that consists of 5E,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid bearing an additional 4-hydroxy substituent. (CHEBI:72624)
7-HDoHE
7-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 7-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)
Tricosanoic acid
Tricosanoic acid, also known as N-tricosanoate or 22FA, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tricosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tricosanoic acid is a potentially toxic compound. Constituent of Citrus bergamia (bergamot orange) oil Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant. Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant.
Resolvin D5
Resolvin D5 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225) [HMDB] Resolvin D5 is an autacoid resolvin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. The bioactive local mediators, or autacoids, that require enzymatic generation from the omega-3 essential fatty acid EPA were first identified in resolving inflammatory exudates in vivo and carry potent stereoselective biological actions. Resolvins of the E (RvE) series are derived from eicosapentaenoic acid (EPA). Those derived from docosahexaenoic acid (DHA) were termed resolvins of the D series, for example resolvin D1 (RvD1).Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The term resolvins (resolution-phase interaction products) was first introduced to signify that these new structures were endogenous mediators, biosynthesized in the resolution phase of inflammatory exudates, possessing very potent anti-inflammatory and immunoregulatory actions. These actions include reducing neutrophil traffic, regulating cytokine and reactive oxygen species, and lowering the magnitude of the response. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225).
8-HDoHE
8-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 8-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)
16-HDoHE
16-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 16-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)
11-HDoHE
11-HDoHE is an autoxidation product of docosahexaenoic acid DHA. 11-HDoHE is a long-chain polyunsaturated fatty acid that is any docosahexaenoic acid bearing a single hydroxy substituent. An oxidation product of docosahexaenoic acid metabolism. (CHEBI:72790)
10-HDoHE
10-HDoHE is an autoxidation product of docosahexaenoic acid (DHA) in vitro. It is also produced from incubations of DHA in rat liver, brain, and intestinal microsomes. (±)10-HDoHE is a potential marker of oxidative stress in brain and retina where DHA is an abundant polyunsaturated fatty acid. (http://bioreagent.bertinpharma.com)
Cetoleic acid
Cetoleic acid is a poly-unsaturated fatty acid. Source: fish oils and rapeseed. Found as a lipid membrane component.
(S)-Neolitsine
(S)-Neolitsine is found in herbs and spices. (S)-Neolitsine is an alkaloid from the leaves of Laurus nobilis (bay laurel).
Lumequic acid
Lumequic acid is found in fruits. Lumequic acid is isolated from seed oil of Ximenia americana (tallow nut Isolated from seed oil of Ximenia americana (tallow nut). Lumequic acid is found in fruits.
Melissic acid A
Melissic acid A is found in fats and oils. Melissic acid A is found in some plant waxes, e.g. cotto Found in some plant waxes, e.g. cotton
4,8,12,15,19-Docosapentaenoic acid
4,8,12,15,19-Docosapentaenoic acid is found in fats and oils. 4,8,12,15,19-Docosapentaenoic acid is a constituent of many fish oils e.g. sardine, mackerel and herring. Constituent of many fish oils e.g. sardine, mackerel and herring. 4,8,12,15,19-Docosapentaenoic acid is found in fats and oils and fishes.
2(R)-hydroxydocosanoic acid
Alpha-hydroxybehenic acid, also known as A-hydroxydocosanoate or A-hydroxybehenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, alpha-hydroxybehenic acid is considered to be a fatty acid lipid molecule. Alpha-hydroxybehenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Alpha-hydroxybehenic acid can be synthesized from docosanoic acid. Alpha-hydroxybehenic acid can also be synthesized into N-(2-hydroxybehenoyl)-D-galactosylsphingosine. Alpha-hydroxybehenic acid can be found in black elderberry, which makes alpha-hydroxybehenic acid a potential biomarker for the consumption of this food product. 2(R)-Hydroxydocosanoic acid is a long-chain hydroxy fatty acid. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.
28-Methyl-27-nonacosenoic acid
28-Methyl-27-nonacosenoic acid is a constituent of Piper retrofractum (Javanese long pepper) Constituent of Piper retrofractum (Javanese long pepper).
Tetracosahexaenoic acid
The formation of docosahexaenoic acid(DHA) involves the production of tetracosahexaenoic acid C24:6n-3) from dietary linolenic acid (C18:3n-3) via a series of elongation and desaturation reactions, followed by beta-oxidation of C24:6n-3 to C22:6n-3. DHA is deficient in patients lacking peroxisomes.(PMID: 11734571). The formation of docosahexaenoic acid(DHA) involves the production of tetracosahexaenoic acid C24:6n-3) from dietary linolenic acid (C18:3n-3) via a series of elongation and desaturation reactions, followed by beta-oxidation of C24:6n-3 to C22:6n-3.
Heptacosanoic acid
Heptacosanoic acid is a fatty acid found in follicular casts (the abnormal impactation of a sebaceous follicle) implicated as the preclinical lesion of acne vulgaris. (PMID: 2940302). Heptacosanoic acid is one of the fatty acids found that contribute to a significant increase in the microviscosity of erythrocyte membranes in patients affected with adrenoleukodystrophy (ALD) and adrenomyeloneuropathy (AMN). (PMID: 6874949). Heptacosanoic acid has been found in the adrenal cortex and brain, in adrenoleukodystrophy and Zellweger syndrome in humans. (PMID: 3806133). Heptacosanoic acid has been found in blood and tissues of patients with different genetic peroxisomal disorder (Refsums disease, X-linked adrenoleukodystrophy, neonatal adrenoleukodystrophy or Zellweger syndrome). (PMID: 2474624). Heptacosanoic acid is a fatty acid found in follicular casts (the abnormal impactation of a sebaceous follicle) implicated as the preclinical lesion of acne vulgaris. (PMID: 2940302)
Nonacosanoic acid
Nonacosanoic acid is a normal human fatty acid found in many tissues as constituents of cceramides (the major component of the stratum corneum) (PMID: 12190865), in lipids in normal brain white matter (PMID: 8515276), and the sebaceous follicle (PMID: 2940302). Nonacosanoic acid is a normal human fatty acid found in many tissues as constituents of cceramides (the major component of the stratum corneum) (PMID: 12190865), in lipids in normal brain white matter (PMID: 8515276), and the sebaceous follicle (PMID: 2940302).
2-Hydroxy-22-methyltetracosanoic acid
2-Hydroxy-22-methyltetracosanoic acid is found in lanolin wool fat. Found in lanolin wool fat
19,20-DiHDPA
19,20-DiHDPA is one of the major metabolites produced when Docosahexaenoic acid (DHA) is incubated with NADPH-supplemented rat liver microsomes. Docosahexaenoic acid (DHA) is an essential fatty acid and the most abundant omega-3 fatty acid in neural tissues, especially in the retina and brain. DHA is also slowly metabolized by monkey seminal vesicles to 19,20-DiHDPA. The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the omega-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase. (PMID: 1742320) [HMDB] 19,20-DiHDPA is one of the major metabolites produced when Docosahexaenoic acid (DHA) is incubated with NADPH-supplemented rat liver microsomes. Docosahexaenoic acid (DHA) is an essential fatty acid and the most abundant omega-3 fatty acid in neural tissues, especially in the retina and brain. DHA is also slowly metabolized by monkey seminal vesicles to 19,20-DiHDPA. The route of production likely proceeds through cytochrome P450-catalyzed epoxidation at the omega-3 double bond, followed by conversion to the vicinal diols by epoxide hydrolase. (PMID: 1742320).
Neuroprotectin D1
Neuroprotectin D1 is an autacoid protectin. Autacoids are chemical mediators including the families of resolvins and protectins, defined by their potent bioactions and novel chemical structures. They require enzymatic generation from docosanoids, oxygenated products from docosahexaenoic acid (DHA), which specifically possess a conjugated triene double-bond system in their structures, are denoted protectins. The protectins demonstrate anti-inflammatory and neuroprotective actions in vivo. Resolvins and protectins have specific stereoselective actions which evoke biological actions in the nanogram range in vivo and are natural exudate products. Resolvins and protectins as distinct chemical families join the lipoxins as potent agonists of endogenous anti-inflammation and are proresolving chemical mediators of interest in human disease as potential new approaches to treatment. The terms protectin and neuroprotectin [the term applied to protectin that is generated in the neural tissues] were introduced given the anti-inflammatory and protective actions of the 10,17-docosatriene in neural systems, stroke, and animal models of Alzheimers disease. The prefix in neuroprotectin (NPD1) provides a local pathway address for the biosynthesis and action of this molecule. In recent years, investigators have recognized inflammation as playing a key role in many prevalent diseases not previously considered to be of inflammatory etiology. These include Alzheimers disease, cardiovascular disease, and cancer, which now join those well-appreciated inflammatory disorders such as arthritis and periodontal disease. Identifying the molecular mechanism(s) that underlie the many reports of the benefits of dietary omega-3 PUFAs remains an important challenge for nutrition and medicine. Thus, that these new mediator families, resolvins and protectins, are biosynthesized from EPA and DHA, act locally, and possess potent, novel bioactions is of interest to researchers. (PMID: 17090225).
Tetracosatetraenoic acid (24:4n-6)
Tetracosatetraenoic acid n-6 is metabolized to radiolabelled monohydroxylated fatty acids (predominantly the 9-hydroxy positional isomer) but not to other lipoxygenase or cyclooxygenase products by the calcium ionophore-stimulated cells. (PMID: 8049246). Oxidation of tetracosatetraenoic acid n-6 is relatively normal in adrenoleukodystrophy cells and in the cells from one PD,peroxisomal disease patient. Tetracosatetraenoic acid n-6 is metabolized to radiolabelled monohydroxylated fatty acids (predominantly the 9-hydroxy positional isomer) but not to other lipoxygenase or cyclooxygenase products by the calcium ionophore-stimulated cells.
Tetracosapentaenoic acid (24:5n-6)
Tetracosapentaenioc acid is intermediate of Linolenic acid metabolism. [HMDB] Tetracosapentaenioc acid is intermediate of Linolenic acid metabolism.
Tetracosapentaenoic acid (24:5n-3)
Tetracosapentaenioc acid is intermediate of alpha-Linolenic acid metabolism. [HMDB] Tetracosapentaenioc acid is intermediate of alpha-Linolenic acid metabolism.
Tetracosahexaenoic acid (24:6n-3)
6,9,12,15,18,21-Tetracosahexaenoic acid (24:6n-3) is one of the n-3 PUFA and is a very long chain fatty acid. Distribution of 24:6n-3 in marine organisms was investigated by several researchers. Takagi et al. reported relatively high contents of 24:6n-3 in sea lilies and brittle stars (4–10\\% of total fatty acids). High 24:6n-3 content was also found in marine coelenterates. In some edible fishes, 24:6n-3 was detected at significant levels (0–10\\% of total fatty acids).The existence of 24:6n-3 in mammalian tissues was reported with other very long chain fatty acids in the spermatozoa,the retina, and the brain. Voss et al. reported that 24:6n-3 is formed as an intermediate in the metabolic pathway from 20:5n-3 to 22:6n-3 in rat liver. Even though 24:6n-3 is a PUFA existing in fish and mammalian species, physiological functions of 24:6n-3 have not been studied. As functions to be studied, anti-inflammatory and antiallergic. effects of 24:6n-3 are noteworthy because these events are known to be closely related to the unsaturated fatty acid metabolism such as in the arachidonic acid cascade, and 20:5n-3 and 22:6n-3 were reported to suppress inflammatory actions by influencing arachidonic acid metabolism.s24:6n-3 could inhibit the antigen-stimulated production of LT-related compounds as well as other n-3 polyunsaturated fatty acids (PUFA) such as eicosapentaenoic. acid (20:5n-3) and docosahexaenoic acid (22:6n-3), which are major n-3 PUFA in fish oils; 24:6n-3 was also shown to reduce the histamine content in MC/9 cells at 25 uM (27\\% reduction from the control), and the effect was diminished with increase of the fatty acid concentration (up to 100 uM). These two n-3 PUFA, 20:5n-3 and 22:6n-3, also reduced the histamine content (16 and 20\\% reduction at 25 μM, respectively), whereas arachidonic acid (20:4n-6) increased it (18\\% increase at 25 μM).
(E)-2-Tetracosenoic acid
(E)-2-Tetracosenoic acid is found in cereals and cereal products. (E)-2-Tetracosenoic acid is isolated from the leaf wax of durum whea Isolated from the leaf wax of durum wheat. (E)-2-Tetracosenoic acid is found in cereals and cereal products.
8-Dotriacontenoic acid
8-Dotriacontenoic acid is found in green vegetables. 8-Dotriacontenoic acid is a constituent of Centella asiatica (Asiatic pennywort) Constituent of Centella asiatica (Asiatic pennywort). 8-Dotriacontenoic acid is found in herbs and spices and green vegetables.
Catelaidic acid
Catelaidic acid is found in fats and oils. Catelaidic acid is a constituent of partially hydrogenated fish oil Constituent of partially hydrogenated fish oil. Catelaidic acid is found in fats and oils and fishes.
Tetracosahexaenoic acid, n-3
This compound belongs to the family of Straight Chain Fatty Acids. These are fatty acids with a straight aliphatic chain.
(4Z,7Z,11E,13Z,16Z,19Z)-10-Hydroperoxydocosahexaenoic acid
(4Z,7Z,11E,13Z,16Z,19Z)-10-Hydroperoxydocosahexaenoic acid, also known as 10-HPDoHE or 10-peroxy-docosahexaenoic acid, is considered to be a practically insoluble (in water) and relatively neutral molecule. (4Z,7Z,11E,13Z,16Z,19Z)-10-Hydroperoxydocosahexaenoic acid can be biosynthesized from all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.
(4Z,7Z,9E,13Z,16Z,19Z)-11-Hydroperoxydocosahexaenoic acid
(4Z,7Z,9E,13Z,16Z,19Z)-11-Hydroperoxydocosahexaenoic acid, also known as 11-HPDoHE or 11-peroxy-docosahexaenoic acid, is considered to be a practically insoluble (in water) and relatively neutral molecule. (4Z,7Z,9E,13Z,16Z,19Z)-11-Hydroperoxydocosahexaenoic acid can be biosynthesized from all-cis-docosa-4,7,10,13,16,19-hexaenoic acid.
17Z-hexacosenoic acid
17Z-hexacosenoic acid is also known as C26:1N-9 or 17cis-Hexacosenoate. 17Z-hexacosenoic acid is considered to be practically insoluble (in water) and acidic. 17Z-hexacosenoic acid is a fatty acid lipid molecule
14-oxo-DoHE(1-)
14-oxo-DoHE(1-) is also known as 14-oxo-(4Z,7Z,10Z,12E,16Z,19Z)-Docosahexaenoate. 14-oxo-DoHE(1-) is considered to be practically insoluble (in water) and acidic
FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14-O-22:6(4Z,7Z,10Z,13Z,16Z,19Z))
Branched fatty acid esters of hydroxy fatty acids (FAHFAs) are endogenous lipids found in adipose tissue and serum that correlate with insulin sensitivity and are reduced in insulin-resistant humans. Structurally, they are characterized by a branched ester linkage between a fatty acid and a hydroxy-fatty acid. Different positions of the branched ester on the hydroxy fatty acid results in different isomers. FAHFA(22:6(4Z,7Z,10Z,13Z,16Z,19Z)/14-O-22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, is formed from the condensation of the carboxy group of docosahexaenoic acid (DHA) with the hydroxy group of 14-hydroxydocosahexaenoic acid. It is alternatively named 14-DHAHDHA since it is the 14-hydroxy isomer of the DHAHDLA (docosahexaenoic acid-hydroxydocosahexaenoic acid) family.
4,7,10,13,16-Docosapentaenoic acid
Docosapentaenoic acid is fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans.
7,10,13,16,19-Docosapentaenoic acid
7,8,17-trihydroxy-4,9,11,13,15,19-docosahexaenoic acid
Leptomycin B
15-Docosenoic acid
15-docosenoic acid is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 15-docosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 15-docosenoic acid can be found in peanut, which makes 15-docosenoic acid a potential biomarker for the consumption of this food product.
Docosenic acid
Docosenic acid, also known as docosenate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosenic acid is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Docosenic acid can be found in peanut, which makes docosenic acid a potential biomarker for the consumption of this food product.
Docosenoic acid
Docosenoic acid, also known as docosenoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosenoic acid is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Docosenoic acid can be found in common buckwheat, which makes docosenoic acid a potential biomarker for the consumption of this food product.
Melissic acid
Melissic acid, also known as melissate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, melissic acid is considered to be a fatty acid lipid molecule. Melissic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Melissic acid can be found in dandelion and orange mint, which makes melissic acid a potential biomarker for the consumption of these food products. Melissic acid (or triacontanoic acid) is a saturated fatty acid .
24-Hydroxytetracosanoic acid
24-hydroxytetracosanoic acid, also known as 24-hydroxylignoceric acid or omega-hydroxylignocerate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, 24-hydroxytetracosanoic acid is considered to be a fatty acid lipid molecule. 24-hydroxytetracosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 24-hydroxytetracosanoic acid can be found in potato, which makes 24-hydroxytetracosanoic acid a potential biomarker for the consumption of this food product.
Tetracosanedioic acid
Tetracosanedioic acid, also known as tetracosanedioate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, tetracosanedioic acid is considered to be a fatty acid lipid molecule. Tetracosanedioic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Tetracosanedioic acid can be found in potato, which makes tetracosanedioic acid a potential biomarker for the consumption of this food product.
(15Z)-tetracosenoate
(15z)-tetracosenoate, also known as nervonate or (Z)-15-tetracosenoic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms (15z)-tetracosenoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (15z)-tetracosenoate can be found in a number of food items such as flaxseed, star fruit, sweet basil, and breadnut tree seed, which makes (15z)-tetracosenoate a potential biomarker for the consumption of these food products.
22-hydroxy-3-oxochol-4-en-24-oyl-CoA
22-hydroxy-3-oxochol-4-en-24-oyl-coa is practically insoluble (in water) and an extremely strong acidic compound (based on its pKa). 22-hydroxy-3-oxochol-4-en-24-oyl-coa can be found in a number of food items such as longan, radish, napa cabbage, and rocket salad, which makes 22-hydroxy-3-oxochol-4-en-24-oyl-coa a potential biomarker for the consumption of these food products.
22-hydroxydocosanoate
22-hydroxydocosanoate, also known as phellonate or omega-hydroxy behenic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 22-hydroxydocosanoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 22-hydroxydocosanoate can be found in a number of food items such as sesbania flower, chinese cabbage, jute, and sapodilla, which makes 22-hydroxydocosanoate a potential biomarker for the consumption of these food products.
22-oxo-docosanoate
22-oxo-docosanoate, also known as 22-oxobehenate or 22-oxo-c22:0(1-), is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 22-oxo-docosanoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 22-oxo-docosanoate can be found in a number of food items such as strawberry guava, fig, sea-buckthornberry, and rowal, which makes 22-oxo-docosanoate a potential biomarker for the consumption of these food products.
all-cis-7,10,13,16,19-docosapentaenoate
All-cis-7,10,13,16,19-docosapentaenoate, also known as N-3 docosapentaenoic acid or c22:5(omega-3)(1-), is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. All-cis-7,10,13,16,19-docosapentaenoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). All-cis-7,10,13,16,19-docosapentaenoate can be found in a number of food items such as grapefruit/pummelo hybrid, chia, capers, and muscadine grape, which makes all-cis-7,10,13,16,19-docosapentaenoate a potential biomarker for the consumption of these food products.
Behenate
Behenate, also known as docosanoate or behenic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Behenate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Behenate can be found in a number of food items such as winter savory, chinese broccoli, radish, and globe artichoke, which makes behenate a potential biomarker for the consumption of these food products. Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 ¬∞C and boiling point of 306 ¬∞C . Behenate, also known as docosanoate or behenic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Behenate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Behenate can be found in a number of food items such as winter savory, chinese broccoli, radish, and globe artichoke, which makes behenate a potential biomarker for the consumption of these food products. Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 °C and boiling point of 306 °C .
docosanedioate
Docosanedioate, also known as docosanedioic acid or c22:0-dca(2-), is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Docosanedioate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Docosanedioate can be found in a number of food items such as pomes, green zucchini, pot marjoram, and rowal, which makes docosanedioate a potential biomarker for the consumption of these food products. Docosanedioic acid is a dicarboxylic acid with the linear formula HOOC(CH2)20COOH .
