Classification Term: 1732
Straight chain fatty acids (ontology term: CHEMONTID:0000333)
Fatty acids with a straight aliphatic chain." []
found 24 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.
But-2-enoic acid
But-2-enoic acid, also known as (2E)-2-butenoate or alpha-crotonic acid, belongs to the class of organic compounds known as straight chain organic acids. These are organic acids with a straight aliphatic chain. But-2-enoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Food flavour component KEIO_ID C093 NSC 8751 is an endogenous metabolite. NSC 8751 is an endogenous metabolite.
Daminozide
D006133 - Growth Substances > D010937 - Plant Growth Regulators CONFIDENCE standard compound; INTERNAL_ID 2629 D010575 - Pesticides > D006540 - Herbicides D016573 - Agrochemicals KEIO_ID D173 Daminozide, a plant growth regulator, is a selective inhibitor of the human KDM2/7 histone demethylases, with IC50s of 0.55, 1.5 and 2.1 μM for PHF8, KDM2A, and KIAA1718, respectively. Daminozide has >100-fold selectivity for KDM2/7 subfamily versus other demethylase subfamily members tested[1][2].
Succinic acid semialdehyde
Succinic acid semialdehyde (or succinate semialdehyde) is an intermediate in the catabolism of gamma-aminobutyrate or GABA (PMID:16435183). It is formed from GABA by the action of GABA transaminase, which leads to the production of succinate semialdehyde and alanine. The resulting succinate semialdehyde is further oxidized by succinate semialdehyde dehydrogenase to become succinic acid, which also yields NADPH. Under certain situations, high levels of succinate semialdehyde can function as a neurotoxin and a metabotoxin. A neurotoxin is a compound that causes damage to the brain and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Elevated serum levels of succinate semialdehyde are found in succinic semialdehyde dehydrogenase (SSADH) deficiency (gamma-hydroxybutyric aciduria), a rare neurometabolic disorder of gamma-aminobutyric acid (GABA) degradation. Symptoms include motor delay, hypotonia, speech delay, autistic features, seizures, and ataxia. Patients also exhibit behavioural problems such as attention deficit, hyperactivity, anxiety, or aggression (PMID:18622364). Succinate semialdehyde is considered a reactive carbonyl and may lead to increased oxidative stress. This stress is believed to contribute to the formation of free radicals in the brain tissue of animal models induced with SSADH deficiency, which further leads to secondary cell damage and death. Additionally, oxidative stress may be responsible for the loss of striatal dopamine, which may contribute to the neuropathology of SSADH deficiency. Succinic acid semialdehyde is an intermediate in the catabolism of gamma-aminobutyrate (PMID 16435183). Succinate semialdehyde dehydrogenase is an enzyme that catalyses the reaction of succinate semialdehyde and NAD+ to form succinate and NADH. Succinic semialdehyde dehydrogenase (SSADH) deficiency (gamma-hydroxybutyric aciduria) is a rare neurometabolic disorder of gamma-aminobutyric acid degradation. Symptoms include motor delay, hypotonia, speech delay, autistic features, seizures, and ataxia. Patients also exhibit behavioral problems, such as attention deficit, hyperactivity, anxiety, or aggression. (PMID: 18622364) [HMDB]. Succinic acid semialdehyde is found in many foods, some of which are yellow zucchini, japanese chestnut, banana, and pineappple sage.
Valerate
Valeric acid, or pentanoic acid, is a straight chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low molecular weight carboxylic acids, it has a very unpleasant odor. Valeric acid is commonly found in human feces, with an average concentration of 2.4 umol/g feces (range of 0.6-3.8 umol/g) (PMID:6740214). Valeric acid is produced by the gut microbiota, typically Clostridia species and other gut bacterial species such as Megasphaera massiliensis MRx0029 (PMID:30052654) via the condensation of ethanol with propionic acid (PMID:18116989). Valeric acid is largely considered as a gut microbial metabolite. Recently, valeric acid has been found to exert strong gut protective effects. Studies involving mice that received high doses of radiation showed that valeric acid replenishment (via oral gavage) elevated the survival rate of irradiated mice, protected hematogenic organs (such as the thymus and spleen), improved gastrointestinal (GI) tract function and enhanced intestinal epithelial integrity (PMID:31931652 ). Valeric acid was also found to restore the enteric bacteria taxonomic proportions and reprogram the small intestinal protein profile to normal levels. Valeric acid, like butyric acid, also appears to be a potent histone deacetylase (HDAC) inhibitor. High levels of HDAC proteins have been implicated in a variety of disease pathologies, from cancer and colitis to cardiovascular disease and neurodegeneration (PMID:30052654). Valeric acid is also found in certain plants, specifically in the perennial flowering plant valerian (Valeriana officinalis), from which it gets its name. Industrially valeric acid is primarily used is in the synthesis of its esters. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Ethyl valerate and pentyl valerate are used as food additives because of their fruity flavours. Hydrolysis of these valerate-containing food additives in the gut can also lead to the appearance of valerate in blood, urine and stool samples. Minor constituent of biological systems e.g. yeast fat, some plant oilsand is also present in blue cheeses, wines, apple, banana, morello cherry, cooked shrimp, scallop, roasted peanut, roasted filberts and other foodstuffs. Flavouring agent. Pentanoic acid is found in many foods, some of which are red raspberry, pepper (c. frutescens), tea, and fats and oils. KEIO_ID V002
Butyric acid
Butyric acid is a short-chain fatty acid (SCFA) formed in the mammalian colon by bacterial fermentation of carbohydrates (including dietary fibre). It is a straight-chain alkyl carboxylic acid that appears as an oily, colorless liquid with an unpleasant (rancid butter) odor. The name butyric acid comes from the Greek word for "butter", the substance in which it was first found. Triglycerides of butyric acid constitute 3‚Äì4\\% of butter. When butter goes rancid, butyric acid is liberated from the short-chain triglycerides via hydrolysis. Butyric acid is a widely distributed SCFA and is found in all organisms ranging from bacteria to plants to animals. It is present in animal fat and plant oils, bovine milk, breast milk, butter, parmesan cheese, body odor and vomit. While butyric acid has an unpleasant odor, it does have a pleasant buttery taste. As a result, butyric acid is used as a flavoring agent in food manufacturing. Low-molecular-weight esters of butyric acid, such as methyl butyrate, also have very pleasant aromas or tastes. As a result, several butyrate esters are used as food and perfume additives. Butyrate is naturally produced by fermentation processes performed by obligate anaerobic bacteria found in the mammalian gut. It is a metabolite of several bacterial genera including Anaerostipes, Coprococcus, Eubacterium, Faecalibacterium and Roseburia (PMID: 12324374; PMID: 27446020). Highly-fermentable fiber residues, such as those from resistant starch, oat bran, pectin, and guar can be transformed by colonic bacteria into butyrate. One study found that resistant starch consistently produces more butyrate than other types of dietary fibre (PMID: 14747692). The production of butyrate from fibres in ruminant animals such as cattle is responsible for the butyrate content of milk and butter. Butyrate has a number of important biological functions and binds to several specific receptors. In humans, butyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2), a G protein-coupled receptor. Like other SCFAs, butyrate is also an agonist at the free fatty acid receptors FFAR2 and FFAR3, which function as nutrient sensors that facilitate the homeostatic control of energy balance. Butyrate is essential to host immune homeostasis (PMID: 25875123). Butyrates effects on the immune system are mediated through the inhibition of class I histone deacetylases (specifically, HDAC1, HDAC2, HDAC3, and HDAC8) and activation of its G-protein coupled receptor targets including HCA2, FFAR2 and FFAR3. Among the short-chain fatty acids, butyrate is the most potent promoter of intestinal regulatory T cells in vitro and the only SCFA that is an HCA2 ligand (PMID: 25741338). Butyrate has been shown to be a critical mediator of the colonic inflammatory response. It possesses both preventive and therapeutic potential to counteract inflammation-mediated ulcerative colitis and colorectal cancer. As a short-chain fatty acid, butyrate is metabolized by mitochondria as an energy source through fatty acid metabolism. In particular, it is an important energy source for cells lining the mammalian colon (colonocytes). Without butyrate, colon cells undergo autophagy (i.e., self-digestion) and die. Butyric acid, also known as butyrate or butanoic acid, is a member of the class of compounds known as straight chain fatty acids. Straight chain fatty acids are fatty acids with a straight aliphatic chain. Thus, butyric acid is considered to be a fatty acid lipid molecule. Butyric acid is soluble (in water) and a weakly acidic compound (based on its pKa). Butyric acid can be found in a number of food items such as cinnamon, pepper (c. baccatum), burdock, and mandarin orange (clementine, tangerine), which makes butyric acid a potential biomarker for the consumption of these food products. Butyric acid can be found primarily in most biofluids, including saliva, breast milk, feces, and cerebrospinal fluid (CSF), as well as throughout most human tissues. Butyric acid exists in all eukaryotes, ranging from yeast to humans. In humans, butyric acid is involved in a couple of metabolic pathways, which include butyrate metabolism and fatty acid biosynthesis. Moreover, butyric acid is found to be associated with aIDS. Butyric acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugène Chevreul. By 1818, he had purified it sufficiently to characterize it. However, Chevreul did not publish his early research on butyric acid; instead, he deposited his findings in manuscript form with the secretary of the Academy of Sciences in Paris, France. Henri Braconnot, a French chemist, was also researching the composition of butter and was publishing his findings, and this led to disputes about priority. As early as 1815, Chevreul claimed that he had found the substance responsible for the smell of butter. By 1817, he published some of his findings regarding the properties of butyric acid and named it. However, it was not until 1823 that he presented the properties of butyric acid in detail. The name of butyric acid comes from the Latin word for butter, butyrum (or buturum), the substance in which butyric acid was first found . If the compound has been ingested, rapid gastric lavage should be performed using 5\\% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of -oximes has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally (T3DB). D018377 - Neurotransmitter Agents > D018494 - Histamine Agents > D006633 - Histamine Antagonists KEIO_ID B006
5-Acetamidovalerate
5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate. Experiment using DL-{4,5-3H}lysine showed 5-acetamidovalerate as the major product. If radiolabeled N6-acetyl-L-lysine was used with added α-ketoglutarate, and pyridoxal phosphate, radiolabeled 2-keto-6-acetamidocaproate was produced. α-Ketoglutarate was preferred over pyruvate, and there was little or no dependence on pyridoxal phosphate. If thiamine pyrophosphate and NAD were added to a similar reaction, virtually all of the label was in 5-acetamidovalerate. If labeled 5-acetamidovalerate was used, labeled 5-aminovalerate (5-aminopentanoate) was identified. In addition, whole cell cultures of R. leguminicola incubated with labeled 5-acetamidovalerate accumulated radiolabeled glutarate. Whole cell cultures incubated with radiolabeled glutarate produced a mixture of tricarboxylic acid cycle acids and other carboxylic acids. 5-Acetamidovalerate is involved in the lysine degradation III pathway. It can be generated from the enzymatic reduction of 5-aminopentanoate or enzymatic oxidation of 2-keto-6-acetamidocaproate.
Glutarate semialdehyde
In the lysine degradation IV pathway, glutarate semialdehyde reacts with NADP+ and H2O to produce glutarate, NADPH, and H+. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase. In the lysine degradation III pathway, glutarate semialdehyde reacts with NAD+ and H2O to produce glutarate and NADH. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase. In the lysine degradation IV pathway, glutarate semialdehyde reacts with NADP+ and H2O to produce glutarate, NADPH, and H+. In this pathway, glutarate semialdehyde is produced by the reaction between 5-aminopentanoate and 2-ketoglutarate, with L-glutamate as a byproduct. The enzyme responsible for this reaction is 5-aminovalerate aminotransferase.
3-Methylthiopropionic acid
3-methylthiopropionate is one of the metabolites of methionine (especially of D-methionine) and pharmacokinetics of 3-MTP in urine seems to contribute to the clinicopathological investigation of the liver cirrhosis. (PMID 3997054) [HMDB] 3-methylthiopropionate is one of the metabolites of methionine (especially of D-methionine) and pharmacokinetics of 3-MTP in urine seems to contribute to the clinicopathological investigation of the liver cirrhosis. (PMID 3997054). 3-(Methylthio)propionic acid is an intermediate in the methionine metabolism.
Deoxycarnitine
4-Trimethylammoniobutanoic acid, also known as gamma-butyrobetaine (GBB) or 3-dehydroxycarnitine, is a highly water-soluble derivative of gamma-aminobutyric acid (GABA). It is also a precursor of L-carnitine. It is a substrate of gamma butyrobetaine hydroxylase/dioxygenase (also known as BBOX) which catalyzes the formation of L-carnitine from gamma-butyrobetaine, the last step in the L-carnitine biosynthesis pathway. Carnitine is essential for the transport of activated fatty acids across the mitochondrial membrane during mitochondrial beta-oxidation. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase, or the OCTN2 transporter aetiologically, causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, impaired reabsorption by the kidney, and increased urinary loss. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physicochemical properties as well. High-performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile (PMID: 17508264, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.). 3-Dehydroxycarnitine is an acylcarnitine. Numerous disorders have been described that lead to disturbances in energy production and in intermediary metabolism in the organism which are characterized by the production and excretion of unusual acylcarnitines. A mutation in the gene coding for carnitine-acylcarnitine translocase or the OCTN2 transporter aetiologically causes a carnitine deficiency that results in poor intestinal absorption of dietary L-carnitine, its impaired reabsorption by the kidney and, consequently, in increased urinary loss of L-carnitine. Determination of the qualitative pattern of acylcarnitines can be of diagnostic and therapeutic importance. The betaine structure of carnitine requires special analytical procedures for recording. The ionic nature of L-carnitine causes a high water solubility which decreases with increasing chain length of the ester group in the acylcarnitines. Therefore, the distribution of L-carnitine and acylcarnitines in various organs is defined by their function and their physico-chemical properties as well. High performance liquid chromatography (HPLC) permits screening for free and total carnitine, as well as complete quantitative acylcarnitine determination, including the long-chain acylcarnitine profile. (PMID: 17508264, Monatshefte fuer Chemie (2005), 136(8), 1279-1291., Int J Mass Spectrom. 1999;188:39-52.) [HMDB] COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
2-Pentenoic acid
2-Pentenoic acid is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]") It is used as a food additive .
4-Pentenoic acid
4-Pentenoic acid is a flavouring ingredien Flavouring ingredient
Isocrotonic acid
Isocrotonic acid is used in food preservatives.Isocrotonic acid (or quartenylic acid) is the cis analogue of crotonic acid. It is an oil, possessing a smell similar to that of brown sugar. (Wikipedia It is used in food preservatives
3-S-methylmercaptopropionate
3-s-methylmercaptopropionate, also known as 3-methylthiopropionic acid or 3-(methylsulfanyl)propanoic acid, is a member of the class of compounds known as straight chain fatty acids. Straight chain fatty acids are fatty acids with a straight aliphatic chain. 3-s-methylmercaptopropionate is soluble (in water) and a weakly acidic compound (based on its pKa). 3-s-methylmercaptopropionate can be found in a number of food items such as other bread, italian sweet red pepper, triticale, and pot marjoram, which makes 3-s-methylmercaptopropionate a potential biomarker for the consumption of these food products.
