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Citric acid

C6H8O7 (192.027)

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].

Palmitic acid

C16H32O2 (256.2402)

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Crotonoyl-CoA

C25H40N7O17P3S (835.1414)

Crotonoyl-CoA is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of a group of enzymes acyl-Coenzyme A oxidases 1, 2, 3 (E.C.: 1.3.3.6) corresponding to palmitoyl, branched chain, and pristanoyl, respectively, in the peroxisomal fatty acid beta-oxidation, producing hydrogen peroxide. Abnormality of this group of enzymes is linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. It is also a substrate of a group of enzymes called acyl-Coenzyme A dehydrogenase (E.C.:1.3.99-, including 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched chain amino acids in the mitochondria (Rozen et al., 1994). Acyl-Coenzyme A dehydrogenase (1.3.99.3) has shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, medium chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl coenzyme A hydratase (E.C.4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism, benzoate degradation via CoA ligation; in contrast it is the product of this enzyme in the butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-Hydroxybutyryl-CoA dehydratase (E.C.:4.2.1.55), glutaconyl-CoA decarboxylase (E.C.: 4.1.1.70), vinylacetyl-CoA Δ-isomerase (E.C.: 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (E.C.: 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl CoA is produced by glutaryl-Coenzyme A dehydrogenase (E.C.:1.3.99.7) lysine and tryptophan metabolic pathway. This enzyme is linked to type-1glutaric aciduria, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases. [HMDB] Crotonoyl-CoA (CAS: 992-67-6) is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of acyl-coenzyme A oxidases 1, 2, and 3 (EC 1.3.3.6) corresponding to palmitoyl, branched-chain, and pristanoyl, respectively. In peroxisomal fatty acid beta-oxidation, these enzymes produce hydrogen peroxide. Abnormalities in this group of enzymes are linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. Crotonoyl-CoA is also a substrate of a group of enzymes called acyl-coenzyme A dehydrogenases (EC 1.3.99-, 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched-chain amino acids in the mitochondria (PMID: 7698750). Acyl-coenzyme A dehydrogenase has been shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, and medium-chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl-coenzyme A hydratase (EC 4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism as well as benzoate degradation via CoA ligation. Crotonoyl-CoA is the product of this enzyme in butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-hydroxybutyryl-CoA dehydratase (EC 4.2.1.55), glutaconyl-CoA decarboxylase (EC 4.1.1.70), vinylacetyl-CoA delta-isomerase (EC 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (EC 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl-CoA is produced by glutaryl-coenzyme A dehydrogenase (EC 1.3.99.7). This enzyme is linked to glutaric aciduria type I, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases.

Malonyl-CoA

C24H38N7O19P3S (853.1156)

Malonyl-CoA belongs to the class of organic compounds known as acyl-CoAs. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-CoA is considered to be a fatty ester lipid molecule. Malonyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, malonyl-CoA participates in a number of enzymatic reactions. In particular, malonyl-CoA can be biosynthesized from acetyl-CoA; which is mediated by the enzyme acetyl-CoA carboxylase 1. In addition, malonyl-CoA can be converted into malonic acid and coenzyme A; which is catalyzed by the enzyme fatty acid synthase. Outside of the human body, malonyl-CoA has been detected, but not quantified in, several different foods, such as rapes, mamey sapotes, jews ears, pepper (C. chinense), and Alaska wild rhubarbs. This could make malonyl-CoA a potential biomarker for the consumption of these foods. Malonyl-CoA is a coenzyme A derivative that plays a key role in fatty acid synthesis in the cytoplasmic and microsomal systems. Malonyl-coa, also known as malonyl coenzyme a or coenzyme a, s-(hydrogen propanedioate), is a member of the class of compounds known as acyl coas. Acyl coas are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, malonyl-coa is considered to be a fatty ester lipid molecule. Malonyl-coa is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Malonyl-coa can be found in a number of food items such as root vegetables, sourdock, ceylon cinnamon, and buffalo currant, which makes malonyl-coa a potential biomarker for the consumption of these food products. Malonyl-coa exists in E.coli (prokaryote) and yeast (eukaryote).

Oxaloacetate

C4H4O5 (132.0059)

Oxalacetic acid, also known as oxaloacetic acid, keto-oxaloacetate or 2-oxobutanedioate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. Oxalacetic acid is a metabolic intermediate in many processes that occur in animals and plants. It takes part in gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, fatty acid synthesis and the citric acid cycle. Oxalacetic acid exists in all living species, ranging from bacteria to plants to humans. Within humans, oxalacetic acid participates in a number of enzymatic reactions. In particular, oxalacetic acid is an intermediate of the citric acid cycle, where it reacts with acetyl-CoA to form citrate, catalyzed by citrate synthase. It is also involved in gluconeogenesis and the urea cycle. In gluconeogenesis oxaloacetate is decarboxylated and phosphorylated by phosphoenolpyruvate carboxykinase and becomes 2-phosphoenolpyruvate using guanosine triphosphate (GTP) as phosphate source. In the urea cycle, malate is acted on by malate dehydrogenase to become oxaloacetate, producing a molecule of NADH. After that, oxaloacetate can be recycled to aspartate, as this recycling maintains the flow of nitrogen into the cell. In mice, injections of oxalacetic acid have been shown to promote brain mitochondrial biogenesis, activate the insulin signaling pathway, reduce neuroinflammation and activate hippocampal neurogenesis (PMID: 25027327). Oxalacetic acid has also been reported to reduce hyperglycemia in type II diabetes and to extend longevity in C. elegans (PMID: 25027327). Outside of the human body, oxalacetic acid has been detected, but not quantified in, several different foods, such as Persian limes, lemon balms, wild rice, canola, and peanuts. This could make oxalacetic acid a potential biomarker for the consumption of these foods. Oxalacetic acid, also known as ketosuccinic acid or oxaloacetate, belongs to short-chain keto acids and derivatives class of compounds. Those are keto acids with an alkyl chain the contains less than 6 carbon atoms. Thus, oxalacetic acid is considered to be a fatty acid lipid molecule. Oxalacetic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Oxalacetic acid can be synthesized from succinic acid. Oxalacetic acid can also be synthesized into oxaloacetic acid 4-methyl ester. Oxalacetic acid can be found in a number of food items such as daikon radish, sacred lotus, cucurbita (gourd), and tarragon, which makes oxalacetic acid a potential biomarker for the consumption of these food products. Oxalacetic acid can be found primarily in cellular cytoplasm, cerebrospinal fluid (CSF), and urine, as well as in human liver tissue. Oxalacetic acid exists in all living species, ranging from bacteria to humans. In humans, oxalacetic acid is involved in several metabolic pathways, some of which include the oncogenic action of succinate, the oncogenic action of 2-hydroxyglutarate, glycogenosis, type IB, and the oncogenic action of fumarate. Oxalacetic acid is also involved in several metabolic disorders, some of which include the oncogenic action of l-2-hydroxyglutarate in hydroxygluaricaciduria, transfer of acetyl groups into mitochondria, argininemia, and 2-ketoglutarate dehydrogenase complex deficiency. Moreover, oxalacetic acid is found to be associated with anoxia. C274 - Antineoplastic Agent > C177430 - Agent Targeting Cancer Metabolism C26170 - Protective Agent > C1509 - Neuroprotective Agent Oxaloacetic acid (2-Oxosuccinic acid) is a metabolic intermediate involved in several ways, such as citric acid cycle, gluconeogenesis, the urea cycle, the glyoxylate cycle, amino acid synthesis, and fatty acid synthesis[1][2]. Oxaloacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=328-42-7 (retrieved 2024-10-17) (CAS RN: 328-42-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Acetyl-CoA

C23H38N7O17P3S (809.1258)

The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent. The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia)

Pyruvic acid

C3H4O3 (88.016)

Pyruvic acid, also known as 2-oxopropanoic acid or alpha-ketopropionic acid, belongs to alpha-keto acids and derivatives class of compounds. Those are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon. Thus, pyruvic acid is considered to be a fatty acid lipid molecule. Pyruvic acid is soluble (in water) and a moderately acidic compound (based on its pKa). Pyruvic acid can be synthesized from propionic acid. Pyruvic acid is also a parent compound for other transformation products, including but not limited to, 4-hydroxy-3-iodophenylpyruvate, 3-acylpyruvic acid, and methyl pyruvate. Pyruvic acid can be found in a number of food items such as kumquat, groundcherry, coconut, and prunus (cherry, plum), which makes pyruvic acid a potential biomarker for the consumption of these food products. Pyruvic acid can be found primarily in most biofluids, including sweat, blood, urine, and feces, as well as throughout most human tissues. Pyruvic acid exists in all living species, ranging from bacteria to humans. In humans, pyruvic acid is involved in several metabolic pathways, some of which include glycogenosis, type IB, glycolysis, urea cycle, and gluconeogenesis. Pyruvic acid is also involved in several metabolic disorders, some of which include non ketotic hyperglycinemia, pyruvate dehydrogenase complex deficiency, fructose-1,6-diphosphatase deficiency, and 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency. Moreover, pyruvic acid is found to be associated with anoxia, schizophrenia, fumarase deficiency, and meningitis. Pyruvic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pyruvic acid is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. It can also be used to construct the amino acid alanine and can be converted into ethanol or lactic acid via fermentation . Those taking large doses of supplemental pyruvate—usually greater than 5 grams daily—have reported gastrointestinal symptoms, including abdominal discomfort and bloating, gas and diarrhea. One child receiving pyruvate intravenously for restrictive cardiomyopathy died (DrugBank). Pyruvate serves as a biological fuel by being converted to acetyl coenzyme A, which enters the tricarboxylic acid or Krebs cycle where it is metabolized to produce ATP aerobically. Energy can also be obtained anaerobically from pyruvate via its conversion to lactate. Pyruvate injections or perfusions increase contractile function of hearts when metabolizing glucose or fatty acids. This inotropic effect is striking in hearts stunned by ischemia/reperfusion. The inotropic effect of pyruvate requires intracoronary infusion. Among possible mechanisms for this effect are increased generation of ATP and an increase in ATP phosphorylation potential. Another is activation of pyruvate dehydrogenase, promoting its own oxidation by inhibiting pyruvate dehydrogenase kinase. Pyruvate dehydrogenase is inactivated in ischemia myocardium. Yet another is reduction of cytosolic inorganic phosphate concentration. Pyruvate, as an antioxidant, is known to scavenge such reactive oxygen species as hydrogen peroxide and lipid peroxides. Indirectly, supraphysiological levels of pyruvate may increase cellular reduced glutathione (T3DB). Pyruvic acid or pyruvate is a simple alpha-keto acid. It is a three-carbon molecule containing a carboxylic acid group and a ketone functional group. Pyruvate is the simplest alpha-keto acid and according to official nomenclature by IUPAC, it is called alpha-keto propanoic acid. Like other keto acids, pyruvic acid can tautomerize from its ketone form to its enol form, containing a double bond and an alcohol. Pyruvate is found in all living organisms ranging from bacteria to plants to humans. It is intermediate compound in the metabolism of carbohydrates, proteins, and fats. Pyruvate is a key intermediate in several metabolic pathways throughout the cell. In particular, pyruvic acid can be made from glucose through glycolysis, converted back to carbohydrates (such as glucose) via gluconeogenesis, or to fatty acids through a reaction with acetyl-CoA. Pyruvic acid supplies energy to cells through the citric acid cycle (TCA or Krebs cycle) when oxygen is present (aerobic respiration), and alternatively ferments to produce lactate when oxygen is lacking (lactic acid). In glycolysis, phosphoenolpyruvate (PEP) is converted to pyruvate by pyruvate kinase. This reaction is strongly exergonic and irreversible. In gluconeogenesis, it takes two enzymes, pyruvate carboxylase and PEP carboxykinase, to catalyze the reverse transformation of pyruvate to PEP. Pyruvic acid is also a metabolite of Corynebacterium (PMID: 27872963). Pyruvic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=127-17-3 (retrieved 2024-07-01) (CAS RN: 127-17-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats. Pyruvic acid is an intermediate metabolite in the metabolism of carbohydrates, proteins, and fats.

Palmityl-CoA

C37H66N7O17P3S (1005.3449)

Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis. A fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis. [HMDB] COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

3-Hydroxybutyryl-coenzyme A

C25H42N7O18P3S (853.152)

Butyryl-CoA

C25H42N7O17P3S (837.1571)

Butyryl-CoA is an intermediate in the metabolism of Butanoate. It is a substrate for Acyl-coenzyme A oxidase 3 (peroxisomal), 3-ketoacyl-CoA thiolase (mitochondrial), 3-ketoacyl-CoA thiolase (peroxisomal), Acyl-coenzyme A oxidase 1 (peroxisomal), Acyl-CoA dehydrogenase (medium-chain specific, mitochondrial), Acyl-CoA dehydrogenase (long-chain specific, mitochondrial), Acyl-coenzyme A oxidase 2 (peroxisomal), Acetyl-CoA acetyltransferase (mitochondrial), Acetyl-CoA acetyltransferase (cytosolic), Acyl-CoA dehydrogenase (short-chain specific, mitochondrial) and Trifunctional enzyme beta subunit (mitochondrial).