Classification Term: 2270
Tricarboxylic acids and derivatives (ontology term: CHEMONTID:0001986)
Carboxylic acids containing exactly three carboxyl groups." []
found 86 associated metabolites at sub_class metabolite taxonomy ontology rank level.
Ancestor: Carboxylic acids and derivatives
Child Taxonomies: There is no child term of current ontology term.
Citric acid
Citric acid (citrate) is a tricarboxylic acid, an organic acid with three carboxylate groups. Citrate is an intermediate in the TCA cycle (also known as the Tricarboxylic Acid cycle, the Citric Acid cycle or Krebs cycle). The TCA cycle is a central metabolic pathway for all animals, plants, and bacteria. As a result, citrate is found in all living organisms, from bacteria to plants to animals. In the TCA cycle, the enzyme citrate synthase catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate then acts as the substrate for the enzyme known as aconitase and is then converted into aconitic acid. The TCA cycle ends with regeneration of oxaloacetate. This series of chemical reactions in the TCA cycle is the source of two-thirds of the food-derived energy in higher organisms. Citrate can be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis, and into oxaloacetate. Citrate is a positive modulator of this conversion, and allosterically regulates the enzyme acetyl-CoA carboxylase, which is the regulating enzyme in the conversion of acetyl-CoA into malonyl-CoA (the commitment step in fatty acid synthesis). In short, citrate is transported into the cytoplasm, converted into acetyl CoA, which is then converted into malonyl CoA by acetyl CoA carboxylase, which is allosterically modulated by citrate. In mammals and other vertebrates, Citrate is a vital component of bone, helping to regulate the size of apatite crystals (PMID: 21127269). Citric acid is found in citrus fruits, most concentrated in lemons and limes, where it can comprise as much as 8\\\\\% of the dry weight of the fruit. Citric acid is a natural preservative and is also used to add an acidic (sour) taste to foods and carbonated drinks. Because it is one of the stronger edible acids, the dominant use of citric acid is as a flavoring and preservative in food and beverages, especially soft drinks and candies. Citric acid is an excellent chelating agent, binding metals by making them soluble. It is used to remove and discourage the buildup of limescale from boilers and evaporators. It can be used to treat water, which makes it useful in improving the effectiveness of soaps and laundry detergents. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. Intolerance to citric acid in the diet is known to exist. Little information is available as the condition appears to be rare, but like other types of food intolerance it is often described as a "pseudo-allergic" reaction. Citric acid appears as colorless, odorless crystals with an acid taste. Denser than water. (USCG, 1999) Citric acid is a tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms. It has a role as a food acidity regulator, a chelator, an antimicrobial agent and a fundamental metabolite. It is a conjugate acid of a citrate(1-) and a citrate anion. A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium-chelating ability. Citric acid is one of the active ingredients in Phexxi, a non-hormonal contraceptive agent that was approved by the FDA on May 2020. It is also used in combination with magnesium oxide to form magnesium citrate, an osmotic laxative. Citric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Anhydrous citric acid is a Calculi Dissolution Agent and Anti-coagulant. The mechanism of action of anhydrous citric acid is as an Acidifying Activity and Calcium Chelating Activity. The physiologic effect of anhydrous citric acid is by means of Decreased Coagulation Factor Activity. Anhydrous Citric Acid is a tricarboxylic acid found in citrus fruits. Citric acid is used as an excipient in pharmaceutical preparations due to its antioxidant properties. It maintains stability of active ingredients and is used as a preservative. It is also used as an acidulant to control pH and acts as an anticoagulant by chelating calcium in blood. A key intermediate in metabolism. It is an acid compound found in citrus fruits. The salts of citric acid (citrates) can be used as anticoagulants due to their calcium chelating ability. See also: Citric Acid Monohydrate (related). Citrate, also known as anhydrous citric acid or 2-hydroxy-1,2,3-propanetricarboxylic acid, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Citrate is soluble (in water) and a weakly acidic compound (based on its pKa). Citrate can be found in a number of food items such as ucuhuba, loquat, bayberry, and longan, which makes citrate a potential biomarker for the consumption of these food products. Citrate can be found primarily in most biofluids, including saliva, sweat, feces, and blood, as well as throughout all human tissues. Citrate exists in all living species, ranging from bacteria to humans. In humans, citrate is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of fumarate, the oncogenic action of 2-hydroxyglutarate, and congenital lactic acidosis. Citrate is also involved in several metabolic disorders, some of which include 2-ketoglutarate dehydrogenase complex deficiency, pyruvate dehydrogenase deficiency (E2), fumarase deficiency, and glutaminolysis and cancer. Moreover, citrate is found to be associated with lung Cancer, tyrosinemia I, maple syrup urine disease, and propionic acidemia. A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate ion is written as C6H5O73− or C3H5O(COO)33− . A tricarboxylic acid that is propane-1,2,3-tricarboxylic acid bearing a hydroxy substituent at position 2. It is an important metabolite in the pathway of all aerobic organisms. Citric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=77-92-9 (retrieved 2024-07-01) (CAS RN: 77-92-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3]. Citric acid is a natural preservative and food tartness enhancer. Citric acid induces apoptosis and cell cycle arrest at G2/M phase and S phase in HaCaT cells. Citric acid cause oxidative damage of the liver by means of the decrease of antioxidative enzyme activities. Citric acid causes renal toxicity in mice[1][2][3].
Aconitate [cis or trans]
cis-Aconitic acid is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. The enzyme aconitase (aconitate hydratase; EC 4.2.1.3) catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid cycle. Present in apple fruits, maple syrup and passion fruit juice cis-Aconitic acid, also known as (Z)-aconitic acid, plays several important biological roles: Intermediate in the Citric Acid Cycle: cis-Aconitic acid is an intermediate in the tricarboxylic acid (TCA) cycle, also known as the Krebs cycle or citric acid cycle. It is formed from citrate by the enzyme aconitase and is rapidly converted into isocitrate, another key intermediate in the cycle. The TCA cycle is central to cellular respiration, generating energy-rich molecules like NADH and FADH2. Regulation of Aconitase Activity: The conversion of citrate to cis-aconitate and then to isocitrate by aconitase is an important regulatory step in the TCA cycle. This conversion helps in maintaining the balance of the cycle and is influenced by factors like the energy status of the cell. Role in Cholesterol Synthesis: cis-Aconitic acid is also involved in the synthesis of cholesterol. It serves as a precursor for the synthesis of mevalonate, a key intermediate in the cholesterol biosynthesis pathway. Potential Involvement in Disease: Altered metabolism or accumulation of cis-aconitic acid has been associated with certain diseases, including neurodegenerative disorders and cancer. Its role in these conditions is an area of ongoing research. Plant Growth and Development: In plants, cis-aconitic acid has been found to play a role in growth and development, including seed germination and leaf senescence. In summary, cis-aconitic acid is a crucial intermediate in the TCA cycle, impacting energy production and various metabolic pathways in cells. Its role extends to cholesterol synthesis and potentially to various disease processes, highlighting its importance in cellular metabolism and physiology. cis-Aconitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=585-84-2 (retrieved 2024-07-01) (CAS RN: 585-84-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (Z)-Aconitic acid (cis-Aconitic acid) is the cis-isomer of Aconitic acid. (Z)-Aconitic acid (cis-Aconitic acid) is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid. (Z)-Aconitic acid (cis-Aconitic acid) is the cis-isomer of Aconitic acid. (Z)-Aconitic acid (cis-Aconitic acid) is an intermediate in the tricarboxylic acid cycle produced by the dehydration of citric acid.
Isocitric acid
Isocitric acid, also known as isocitrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Isocitric acid is a TCA (tricarboxylic acid) cycle intermediate. It is a structural isomer of citric acid and is formed from citrate with the help of the enzyme aconitase. More specifically, Isocitric acid is synthesized from citric acid via the intermediate cis-aconitic acid by the enzyme aconitase (aconitate hydratase). Isocitrate is acted upon by isocitrate dehydrogenase (IDH) to form alpha-ketoglutarate. This is a two-step process, which involves oxidation of isocitrate to oxalosuccinate (a ketone), followed by the decarboxylation of the carboxyl group beta to the ketone, forming alpha-ketoglutarate. In humans, IDH exists in three isoforms: IDH3 catalyzes the third step of the citric acid cycle while converting NAD+ to NADH in the mitochondria. The isoforms IDH1 and IDH2 catalyze the same reaction outside the context of the citric acid cycle and use NADP+ as a cofactor instead of NAD+. They localize to the cytosol as well as the mitochondrion and peroxisome. Isocitric acid exists in all living species, ranging from bacteria to plants to humans. Isocitric acid is a minor organic acid found in most fruit juices, especially in blackberries, youngberries, and boyberries, and in vegetables, especially in carrots. The determination of D-isocitric acid has become of importance in the analysis of fruit juices for the detection of illegal additives (adulteration). Since the quantities of citric and isocitric acids are correlated in fruit juices, a high ratio of citric to isocitric acid can indicate the addition of citric acid as an alduterant. In authentic orange juice, for example, the ratio of citric acid to D-isocitric acid is usually less than 130. Isocitric acid is mostly used in the food industry (food additive) as a food acidulant. The citrate oxidation to isocitrate is catalyzed by the enzyme aconitase. Human prostatic secretion is remarkably rich in citric acid and low aconitase activity will therefore play a significant role in enabling accumulation of high citrate levels (PubMed ID 8115279) [HMDB]. Isocitric acid is found in many foods, some of which are wild carrot, redcurrant, carrot, and soursop. [Spectral] Isocitrate (exact mass = 192.027) and CDP (exact mass = 403.01818) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Isocitric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=320-77-4 (retrieved 2024-07-01) (CAS RN: 320-77-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3]. Isocitric acid is an endogenous metabolite present in Saliva and Cellular_Cytoplasm that can be used for the research of Alzheimer's Disease, Lewy Body Dementia and Anoxia[1][2][3].
2-Methylcitric acid
Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270), which are inherited disorders. MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine (PMID: 17295121). Methylcitric acid (MCA) is elevated in body fluids of patients with propionic acidaemia (PA; OMIM 232000, 232050), methylmalonic aciduria (MMA; OMIM 251000, 251120) and multiple carboxylase deficiency (OMIM 253260, 253270). MCA is formed by condensation of accumulated propionyl- CoA and oxalacetate by the enzyme si-citrate synthase (EC 4.1.3.7). MCA molecule has two stereogenic centers so that it can occur in the form of four stereoisomers. Only two stereoisomers of MCA, (2S, 3S) and (2R, 3S), were found in human urine. (PMID: 17295121) [HMDB] 2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1]. 2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1]. 2-Methylcitric acid (Methylcitric acid) is an endogenous metabolite in the 2-methylcitric acid cycle. 2-Methylcitric acid accumulates in methylmalonic and propionic acidemias and acts as a marker metabolite. 2-Methylcitric acid markedly inhibits ADP-stimulated and uncoupled respiration in mitochondria supported by glutamate[1].
Homocitric acid
Homocitric acid (CAS: 3562-74-1) is a normal urinary organic acid (PMID: 14708889). Homocitric acid is a citric acid analogue found as a minor metabolite in urine samples from patients with propionic acidaemia. Homocitric acid is formed by citrate synthase due to propionyl-CoA carboxylase deficiency (by the citrate synthase condensation reaction of alpha-ketoglutarate with acetyl coenzyme A and propionyl coenzyme A) (PMID: 7850997). Homocitric acid has been identified in the human placenta (PMID: 32033212). Homocitric acid is a normal urinary organic acid. (PMID: 14708889)
(Z)-But-1-ene-1,2,4-tricarboxylate
This compound belongs to the family of Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof).
cis-2-Methylaconitate
cis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742) [HMDB]. cis-2-Methylaconitate is found in many foods, some of which are new zealand spinach, cauliflower, rocket salad, and pepper (c. chinense). cis-2-Methylaconitate is produced due to the dehydration of 2-methylcitrate in 2-methylcitric acid cycle. The cycle is catalyzed by a cofactor-less (PrpD) enzyme or by an aconitase-like (AcnD) enzyme. (PMID: 17567742). cis-2-Methylaconitate has been found to be a microbial metabolite (ECMDB).
Methylisocitric acid
Methylisocitric acid is a product of bacterial metabolism in the gut. It can be produced by 2-methylisocitrate lyase and by 2-methylisocitrate dehydratase. Methylisocitric acid has also been found to be a metabolite of Candida (https://www.tandfonline.com/doi/pdf/10.1080/00021369.1974.10861293). Methylisocitric acid is a product of bacterial metabolism in the gut. It can be produced by 2-methylisocitrate lyase and by 2-methylisocitrate dehydratase. [HMDB]
Oxalosuccinic acid
Oxalosuccinic acid, also known as oxalosuccinate or 1-oxopropane-1,2,3-tricarboxylate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Oxalosuccinic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxalosuccinic acid can be found in a number of food items such as japanese chestnut, poppy, wax apple, and hyssop, which makes oxalosuccinic acid a potential biomarker for the consumption of these food products. Oxalosuccinic acid exists in all living species, ranging from bacteria to humans. Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. Its an alpha-keto compound, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Oxalosuccinate never leaves the active site of the enzyme, however; its unstable and immediately undergoes decarboxylation to produce the 5-carbon compound, alpha-ketoglutarate . Oxalosuccinate is a substrate for cytoplasmic Isocitrate dehydrogenase and mitochondiral Isocitrate dehydrogenase (mitochondrial).
1,2,3-Propanetricarboxylic acid
1,2,3-Propanetricarboxylic acid is found in corn. 1,2,3-Propanetricarboxylic acid is isolated from plants e.g. sugarbeet sap, sap of Acer saccharinum (maple syrup). Propane-1,2,3-tricarboxylic acid, also known as tricarballylic acid, carballylic acid, and beta-carboxyglutaric acid, is a tricarboxylic acid that has three carboxylic acid functional groups. The compound is an inhibitor of the enzyme aconitase and interferes with the Krebs cycle. 1,2,3-Propanetricarboxylic acid can be produced by Bacteroides, Butyrivibrio, Megasphaera, Wolinella and fungi Nectriaceae (PMID:22815244; PMID:16346691). It is also associated with Fumonisins. Fumonisins are fungal toxins produced by Fusarium verticilloides. Detection of this compound indicates presence of fumonisins in gastrointestinal tract. Corn intake or corn contaminated with fumonisins can lead to increased levels of tricarballylic acid (PMID:22815244). Isolated from plants e.g. sugarbeet sap, sap of Acer saccharinum (maple syrup) Tricarballylic acid, a conjugate acid of a?tricarballylate, is a competitive inhibitor of the enzyme aconitate hydratase (aconitase; EC 4.2.1.3) with a Ki value of 0.52 mM[1]. Tricarballylic acid, a conjugate acid of a?tricarballylate, is a competitive inhibitor of the enzyme aconitate hydratase (aconitase; EC 4.2.1.3) with a Ki value of 0.52 mM[1]. Tricarballylic acid, a conjugate acid of a?tricarballylate, is a competitive inhibitor of the enzyme aconitate hydratase (aconitase; EC 4.2.1.3) with a Ki value of 0.52 mM[1].
trans-Aconitic acid
trans-Aconitic acid, also known as trans-aconitate or (e)-aconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. trans-Aconitic acid exists in all living species, ranging from bacteria to humans. trans-Aconitic acid is a dry, musty, and nut tasting compound. Outside of the human body, trans-aconitic acid has been detected, but not quantified in several different foods, such as garden tomato fruits, root vegetables, soy beans, and rices. trans-Aconitic acid is normally present in human urine, and it has been suggested that is present in larger amounts with Reyes syndrome and organic aciduria. trans-Aconitic acid in the urine is a biomarker for the consumption of soy products. trans-Aconitic acid is a substrate of enzyme trans-Aconitic acid 2-methyltransferase (EC2.1.1.144). Isolated from Asarum europaeum, from cane-sugar molasses, roasted chicory root, roasted malt barley, passion fruit, sorghum root and sugar beet. Flavouring agent used in fruit flavours and alcoholic beverages. Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase. Trans-aconitate in the urine is a biomarker for the consumption of soy products. (E)-Aconitic acid is found in many foods, some of which are cereals and cereal products, rice, garden tomato (variety), and root vegetables. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A117 trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase. trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase.
D-threo-Isocitric acid
D-threo-Isocitric acid, also known as isocitrate or isocitrIC ACID, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. D-threo-Isocitric acid exists in all living species, ranging from bacteria to humans. D-threo-Isocitric acid has been detected, but not quantified in several different foods, such as citrus, fruits, common beans, green beans, and yellow wax beans. Found in fruit juices. Occurs in blackberry
(1R,2R)-Isocitric acid
(1R,2R)-Isocitric acid is found in citrus. (1R,2R)-Isocitric acid is found in lemon juice. Found in lemon juice
Triethyl citrate
Triethyl citrate is used in foods as a flavouring agent, solvent and surface-active agent Triethyl citrate is an ester of citric acid. It is a colorless, odorless liquid used as a food additive (E number E1505) to stabilize foams, especially as whipping aid for egg white. In pharmaceutical coatings and plastics It is used in foods as a flavouring agent, solvent and surface-active agent
Garcinia acid
Garcinia acid is found in fruits. Garcinia acid is isolated from Garcinia atroviridis (gelugor), Garcinia indica (kokam) and Garcinia cambogi (-)-Hydroxycitric acid (Garcinia acid) is the principal acid of fruit rinds of Garcinia cambogia. (-)-Hydroxycitric acid is a potent and competitive and orally active inhibitor of ATP citrate lyase. (-)-Hydroxycitric acid suppresses the fatty acid synthesis, lipogenesis, food intake, and induced weight loss[1][2]. (-)-Hydroxycitric acid (Garcinia acid) is the principal acid of fruit rinds of Garcinia cambogia. (-)-Hydroxycitric acid is a potent and competitive inhibitor of ATP citrate lyase. (-)-Hydroxycitric acid suppresses the fatty acid synthesis, lipogenesis, food intake, and induced weight loss[1][2]. (-)-Hydroxycitric acid (Garcinia acid) is the principal acid of fruit rinds of Garcinia cambogia. (-)-Hydroxycitric acid is a potent and competitive and orally active inhibitor of ATP citrate lyase. (-)-Hydroxycitric acid suppresses the fatty acid synthesis, lipogenesis, food intake, and induced weight loss[1][2]. (-)-Hydroxycitric acid (Garcinia acid) is the principal acid of fruit rinds of Garcinia cambogia. (-)-Hydroxycitric acid is a potent and competitive inhibitor of ATP citrate lyase. (-)-Hydroxycitric acid suppresses the fatty acid synthesis, lipogenesis, food intake, and induced weight loss[1][2].
2-Hydroxyestradiol-3-methyl ether
2-Hydroxyestradiol-3-methylether is a methoxylated derivative of 2-hydroxyestradiol. 2-hydroxy estrogen metabolites can be converted to anticarcinogenic methoxylated metabolites (2-methoxyestrone and 2-methoxyestradiol, 2-hydroxyestrone and 2-hydroxyestradiol 3-methyl ether) by catechol O-methyltransferase (PMID: 11172156). 2-hydroxyestradiol 3-methyl ether has been found in the urine of pregnant women (along with other 2-hydroxyestrogen ethers) although the amounts are generally small (less than 5 ug/24 hours). (PMID: 966757).
Dodecanedioylcarnitine
Dodecanedioylcarnitine is classified as a tricarboxylic acid or a Tricarboxylic acid derivative. Tricarboxylic acids are carboxylic acids containing exactly three carboxyl groups. Dodecanedioylcarnitine is considered to be a practically insoluble (in water) and a weak acidic compound. Dodecanedioylcarnitine can be found in blood. A human metabolite taken as a putative food compound of mammalian origin [HMDB]
Sorbitan trioleate
Sorbitan trioleate is a food emulsifie Food emulsifier
Sorbitan tristearate
Sorbitan tristearate is a food emulsifier, stabiliser Sorbitan tristearate, also known as Span 65, is a nonionic surfactant. It is variously used as a dispersing agent, emulsifier, and stabilizer, in food and in aerosol sprays. As a food additive, it has the E number E492 Food emulsifier, stabiliser
Starch acetate
Many uses in processed foods including stabilizer, thickener, moisture control, flavour modifier, release/antisticking agent and firming agent
Monoglyceride citrate
Monoglyceride citrate 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 .
1-Isopropyl citrate
1-Isopropyl citrate is a sequestrant, antioxidant, solvent and vehicle in margarine manufacture. Sequestrant, antioxidant, solvent and vehicle in margarine manuf.
Stearyl citrate
Stearyl citrate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
Fumonisin AK1
Fumonisin AK1 is produced by Fusarium proliferatum. Production by Fusarium proliferatum.
2-Isopropyl citrate
2-Isopropyl citrate is a sequestrant and antioxidant for margarine and other foodstuffs. It is a plasticiser for food contact packaging. Sequestrant and antioxidant for margarine and other foodstuffs. Plasticiser for food contact packaging
2-Stearyl citrate
Antioxidant, sequestrant and emulsifier for use in margarine. Plasticiser for food contact packaging. Antioxidant, sequestrant and emulsifier for use in margarine. Plasticiser for food contact packaging
Ethyl aconitate
Ethyl aconitate is a flavouring ingredient. Prepd. as mixture of mono-, di- and triesters by acid-catalysed esterification of aconitic acid with EtOH or by heating
1,5-Dibutyl methyl hydroxycitrate
1,5-Dibutyl methyl hydroxycitrate is found in fruits. 1,5-Dibutyl methyl hydroxycitrate is a constituent of the fruit of Garcinia atroviridis (gelugor). Constituent of the fruit of Garcinia atroviridis (gelugor). 1,5-Dibutyl methyl hydroxycitrate is found in fruits.
Garcinia lactone dibutyl ester
Garcinia lactone dibutyl ester is found in fruits. Garcinia lactone dibutyl ester is a constituent of the fruit of Garcinia atroviridis (gelugor). Constituent of the fruit of Garcinia atroviridis (gelugor). Garcinia lactone dibutyl ester is found in fruits.
3-Hydroxy-3-carboxymethyl-adipic acid
3-Hydroxy-3-carboxymethyl-adipic acid belongs to the family of Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof)
3-(Carboxymethyl)-3-hydroxypentanedioic acid
3-(Carboxymethyl)-3-hydroxypentanedioic acid belongs to the family of Tricarboxylic Acids and Derivatives. These are organic compounds containing three carboxylic acid groups (or salt/ester derivatives thereof)
Suberoyl-L-carnitine
Suberoyl-L-carnitine is an acylcarnitine. More specifically, it is an suberoic aicd ester of carnitine. Acylcarnitines were first discovered more than 70 year ago (PMID: 13825279). It is believed that there are more than 1000 types of acylcarnitines in the human body. The general role of acylcarnitines is to transport acyl-groups (organic acids and fatty acids) from the cytoplasm into the mitochondria so that they can be broken down to produce energy. This process is known as beta-oxidation. According to a recent review [Dambrova et al. 2021, Physiological Reviews], acylcarnitines (ACs) can be classified into 9 different categories depending on the type and size of their acyl-group: 1) short-chain ACs; 2) medium-chain ACs; 3) long-chain ACs; 4) very long-chain ACs; 5) hydroxy ACs; 6) branched chain ACs; 7) unsaturated ACs; 8) dicarboxylic ACs and 9) miscellaneous ACs. Short-chain ACs have acyl-groups with two to five carbons (C2-C5), medium-chain ACs have acyl-groups with six to thirteen carbons (C6-C13), long-chain ACs have acyl-groups with fourteen to twenty once carbons (C14-C21) and very long-chain ACs have acyl groups with more than 22 carbons. Suberoyl-L-carnitine is therefore classified as a medium chain AC. As a medium-chain acylcarnitine Suberoyl-L-carnitine is somewhat less abundant than short-chain acylcarnitines. These are formed either through esterification with L-carnitine or through the peroxisomal metabolism of longer chain acylcarnitines (PMID: 30540494). Many medium-chain acylcarnitines can serve as useful markers for inherited disorders of fatty acid metabolism. Carnitine octanoyltransferase (CrOT, EC:2.3.1.137) is responsible for the synthesis of all medium-chain (MCAC, C5-C12) and medium-length branched-chain acylcarnitines in peroxisomes (PMID: 10486279). The study of acylcarnitines is an active area of research and it is likely that many novel acylcarnitines will be discovered in the coming years. It is also likely that many novel roles in health and disease will be uncovered. An excellent review of the current state of knowledge for acylcarnitines is available at [Dambrova et al. 2021, Physiological Reviews].
5-(Acetoxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d]oxazole-6,7-diyl diacetate
Urea,3,4-tri-O-acetyl-D-ribopyranosyl)-
Tris(2-carboxyethyl)phosphine
D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents
2,3-(C14-O-C14)Galactosamine-4-phosphate
5-[1-Carboxy-2-(trimethylazaniumyl)ethoxy]-5-oxopentanoate
Fructose citrate
Glucose citrate
Glycomul TO
Imidazole citrate
D004791 - Enzyme Inhibitors
Monoacetyldiglyceride
[(3S,4R,5R)-5-[(1R)-2-Hydroxy-1-octadec-9-enoyloxyethyl]-4-octadec-9-enoyloxyoxolan-3-yl] octadec-9-enoate
Taxine
Nitrogenase
Nitrogenase can be found in soy bean, which makes nitrogenase a potential biomarker for the consumption of this food product. Nitrogenases are enzymes (EC 1.18.6.1EC 1.19.6.1) that are produced by certain bacteria, such as cyanobacteria (blue-green algae). These enzymes are responsible for the reduction of nitrogen (N2) to ammonia (NH3). Nitrogenases are the only family of enzymes known to catalyze this reaction, which is a key step in the process of nitrogen fixation. Nitrogen fixation is required for all forms of life, with nitrogen being essential for the biosynthesis of molecules (nucleotides, amino acids) that create plants, animals and other organisms .
Iron citrate
It is used as a food additive .
Sodium stearoyl 2-lactylate
It is used in foods as a dough strengthener, emulsifier, stabiliser, surface active agent, formulation aid, processing aid and texturiser.
Iron(II) citrate
D018977 - Micronutrients > D014131 - Trace Elements Dietary supplement
Calcium citrate
Emulsifier in foods, dietary supplement. Calcium citrate is an intermediate in the isolation of citric acid from the fermentation process by which citric acid is produced industrially. The citric acid in the broth solution is neutralized by calcium hydroxide, precipitating insoluble calcium citrate. This is then filtered off from the rest of the broth and washed to give clean calcium citrate. Emulsifier in foods, dietary supplement
Iron(III) citrate
V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AE - Drugs for treatment of hyperkalemia and hyperphosphatemia D006401 - Hematologic Agents > D006397 - Hematinics > D005290 - Ferric Compounds Nutrient supplement
Iron(III) ammonium citrate
Anticaking agent, dietary iron supplement. May be used in infant formulas [DFC]. A complex salt of undetermined structure, composed of iron, ammonia and citric acid; there are two types of salts - brown and green - containing different amounts of iron. [JECFA] Anticaking agent, dietary iron supplement. May be used in infant formulas [DFC]
Calcium stearoyl 2-lactylate
It is used in foods as an emulsifier, texturiser, surface-tension control agent and dough conditioner
Manganese citrate
Dietary supplement
Sodium dihydrogen citrate
Preservative. Monosodium citrate, or sodium dihydrogen citrate, is an acid salt with the chemical formula NaH2C6H5O7, or C3H4OH(COOH)2COONa. Since it has two remaining open spots on the citrate anion, it is used as a relatively strong sequestrant. It is used to prevent platelet clumping in blood samples. It is one of the 3 citric acid salts. Preservative
Disodium hydrogen citrate
Preservative. Disodium citrate, or disodium hydrogen citrate, is a sodium acid salt of citric acid (sodium citrate) with the chemical formula Na2HC6H5O7, or Na2H(C3H5O(COO)3). It is one of the 3 citric acid salts. It is used as an antioxidant in food as well as to improve the effects of other antioxidants. It is also used as an acidity regulator and sequestrant. Typical products include gelatin, jam, sweets, ice cream, carbonated beverages, milk powder, wine, and processed cheeses. Preservative
Sodium citrate
It is used in food processing as an emulsifying agent, pH control agent, colour control agent, flavouring agent and modifier. It is used in conjunction with ascorbate or erythorbate derivs. as a cure accelerator in processed meat products. Trisodium citrate, sometimes referred to simply as sodium citrate, possesses a saline, mildly tart flavor. Sodium citrate is chiefly used as a food additive E331, usually for flavor or as a preservative. Sodium citrate is employed as a flavoring agent in certain varieties of club soda. Sodium citrate is common as an ingredient in Bratwurst, lemon-lime and citrus soft drinks, such as Ting, Chinotto, and some Ocean Spray juices, contributing to their tart tastes, and can also be found in such energy drinks as Rockstar and Red Bull. It is used in food processing as an emulsifying agent, pH control agent, colour control agent, flavouring agent and modifier. It is used in conjunction with ascorbate or erythorbate derivs. as a cure accelerator in processed meat products
Potassium citrate
Alkalising and buffering agent. It is used in foods, beverages and oral pharmaceutical formulations. More sol. than Na salts; also used in low-Na foods and as a potassium source in nutritional supplements. Potassium citrate is an effective way to treat/manage gout and arrhythmia, if the patient is hypokalemic. In common with other substances that render the urine alkaline, it may be used to reduce the danger of crystalluria during sulfonamide therapy. Potassium citrate is found in beverages. Alkalising and buffering agent. It is used in foods, beverages and oral pharmaceutical formulations. More sol. than Na salts; also used in low-Na foods and as a potassium source in nutritional supplements
(2R,3S)-2-methylisocitrate
(2r,3s)-2-methylisocitrate, also known as methylisocitric acid or (2s,3r)-3-hydroxybutane-1,2,3-tricarboxylate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups (2r,3s)-2-methylisocitrate is soluble (in water) and a weakly acidic compound (based on its pKa). (2r,3s)-2-methylisocitrate can be found in a number of food items such as green zucchini, cinnamon, fig, and nanking cherry, which makes (2r,3s)-2-methylisocitrate a potential biomarker for the consumption of these food products.
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate can be found in a number of food items such as feijoa, german camomile, sugar apple, and rapini, which makes 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate a potential biomarker for the consumption of these food products.
cyclic- 3,4-O-oxalyl-L-threonate
Cyclic- 3,4-o-oxalyl-l-threonate, also known as 3,4-cyclic oxalyl theronolactone, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Cyclic- 3,4-o-oxalyl-l-threonate is soluble (in water) and a moderately acidic compound (based on its pKa). Cyclic- 3,4-o-oxalyl-l-threonate can be found in a number of food items such as pot marjoram, arrowhead, naranjilla, and corn salad, which makes cyclic- 3,4-o-oxalyl-l-threonate a potential biomarker for the consumption of these food products.
cyclic-2,3-O-oxalyl-L-threonate
Cyclic-2,3-o-oxalyl-l-threonate, also known as 2,3-cyclic oxalyl theronolactone, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Cyclic-2,3-o-oxalyl-l-threonate is soluble (in water) and a moderately acidic compound (based on its pKa). Cyclic-2,3-o-oxalyl-l-threonate can be found in a number of food items such as mustard spinach, ostrich fern, fennel, and malus (crab apple), which makes cyclic-2,3-o-oxalyl-l-threonate a potential biomarker for the consumption of these food products.
D-threo-isocitrate
D-threo-isocitrate, also known as isocitric acid or 1-hydroxytricarballylate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. D-threo-isocitrate is soluble (in water) and a weakly acidic compound (based on its pKa). D-threo-isocitrate can be found in a number of food items such as sunflower, endive, mulberry, and chickpea, which makes D-threo-isocitrate a potential biomarker for the consumption of these food products.
oxalosuccinate
Oxalosuccinic acid, also known as oxalosuccinate or 1-oxopropane-1,2,3-tricarboxylate, belongs to tricarboxylic acids and derivatives class of compounds. Those are carboxylic acids containing exactly three carboxyl groups. Oxalosuccinic acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Oxalosuccinic acid can be found in a number of food items such as japanese chestnut, poppy, wax apple, and hyssop, which makes oxalosuccinic acid a potential biomarker for the consumption of these food products. Oxalosuccinic acid exists in all living species, ranging from bacteria to humans. Oxalosuccinic acid/oxalosuccinate is an unstable 6-carbon intermediate in the tricarboxylic acid cycle. Its an alpha-keto compound, formed during the oxidative decarboxylation of isocitrate to alpha-ketoglutarate, which is catalyzed by the enzyme isocitrate dehydrogenase. Oxalosuccinate never leaves the active site of the enzyme, however; its unstable and immediately undergoes decarboxylation to produce the 5-carbon compound, alpha-ketoglutarate .
