Reaction Process: PathBank:SMP0000025

Coenzyme A

C21H36N7O16P3S (767.1152046)

Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as CoASH or HSCoA. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia). Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia [HMDB]. Coenzyme A is found in many foods, some of which are grape, cowpea, pili nut, and summer savory. Coenzyme A (CoASH) is a ubiquitous and essential cofactor, which is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the oxidation of pyruvate in the citric acid cycle and the metabolism of carboxylic acids, including short- and long-chain fatty acids[1]. Coenzyme A (CoASH) is a ubiquitous and essential cofactor, which is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the oxidation of pyruvate in the citric acid cycle and the metabolism of carboxylic acids, including short- and long-chain fatty acids[1]. Coenzyme A, a ubiquitous essential cofactor, is an acyl group carrier and carbonyl-activating group for the citric acid cycle and fatty acid metabolism. Coenzyme A plays a central role in the metabolism of carboxylic acids, including short- and long-chain fatty acids. Coenzyme A. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=85-61-0 (retrieved 2024-10-17) (CAS RN: 85-61-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Glycerol 3-phosphate

C3H9O6P (172.0136744)

Glycerol 3-phosphate, also known as glycerophosphoric acid or alpha-glycerophosphorate, is a member of the class of compounds known as glycerophosphates. Glycerophosphates are compounds containing a glycerol linked to a phosphate group. Glycerol 3-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Glycerol 3-phosphate can be found in a number of food items such as sacred lotus, common oregano, mixed nuts, and yautia, which makes glycerol 3-phosphate a potential biomarker for the consumption of these food products. Glycerol 3-phosphate can be found primarily in blood, feces, saliva, and urine, as well as in human prostate tissue. Glycerol 3-phosphate exists in all living species, ranging from bacteria to humans. In humans, glycerol 3-phosphate is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-12:0/i-21:0/a-21:0/i-21:0), cardiolipin biosynthesis cl(i-12:0/a-25:0/i-13:0/i-12:0), cardiolipin biosynthesis cl(i-13:0/i-21:0/i-21:0/a-25:0), and cardiolipin biosynthesis cl(i-13:0/a-25:0/i-18:0/a-13:0). Glycerol 3-phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis tg(i-24:0/19:0/16:0), de novo triacylglycerol biosynthesis TG(16:0/22:4(7Z,10Z,13Z,16Z)/16:1(9Z)), de novo triacylglycerol biosynthesis TG(18:0/18:3(9Z,12Z,15Z)/14:1(9Z)), and de novo triacylglycerol biosynthesis TG(18:3(6Z,9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)/20:2(11Z,14Z)). Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia). Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G072

Choline

[C5H14NO]+ (104.10753340000001)

Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer. Nutritional supplement. Occurs free and combined in many animal and vegetable foods with highest concentrations found in egg yolk, meat, fish, milk, cereaks and legumes Choline. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=62-49-7 (retrieved 2024-06-29) (CAS RN: 62-49-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Acetylcholine

[C7H16NO2]+ (146.1180976)

Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID:17284361, 17011181, 15556286). Acetylcholine has been found to be a microbial product, urinary acetylcholine is produced by Lactobacillus (PMID:24621061). S - Sensory organs > S01 - Ophthalmologicals > S01E - Antiglaucoma preparations and miotics > S01EB - Parasympathomimetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists Acquisition and generation of the data is financially supported in part by CREST/JST. C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents IPB_RECORD: 232; CONFIDENCE confident structure COVID info from COVID-19 Disease Map Corona-virus KEIO_ID A060 Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Choline phosphate

[C5H15NO4P]+ (184.073866)

Phosphorylcholine, also known as choline phosphate or N-trimethyl-2-aminoethylphosphonate, is a member of the class of compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Phosphorylcholine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Phosphorylcholine can be found in a number of food items such as grapefruit, lime, black cabbage, and barley, which makes phosphorylcholine a potential biomarker for the consumption of these food products. Phosphorylcholine can be found primarily in most biofluids, including urine, blood, saliva, and cerebrospinal fluid (CSF), as well as throughout most human tissues. Phosphorylcholine exists in all eukaryotes, ranging from yeast to humans. In humans, phosphorylcholine is involved in several metabolic pathways, some of which include phosphatidylcholine biosynthesis PC(13D5/9D5), phosphatidylcholine biosynthesis PC(22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)), phosphatidylcholine biosynthesis PC(14:0/20:1(11Z)), and phosphatidylcholine biosynthesis PC(11D5/9D5). Phosphorylcholine is also involved in few metabolic disorders, which include fabry disease, gaucher disease, and krabbe disease. Moreover, phosphorylcholine is found to be associated with alzheimers disease and multi-infarct dementia. Phosphorylcholine (abbreviated ChoP) is the hydrophilic polar head group of some phospholipids, which is composed of a negatively charged phosphate bonded to a small, positively charged choline group. Phosphorylcholine is part of platelet-activating factor; the phospholipid phosphatidylcholine as well as sphingomyelin, the only phospholipid of the membrane that is not built with a glycerol backbone. Treatment of cell membranes, like those of RBCs, by certain enzymes, like some phospholipase A2 renders the phosphorylcholine moiety exposed to the external aqueous phase, and thus accessible for recognition by the immune system. Antibodies against phosphorylcholine are naturally occurring autoantibodies that are created by CD5+/B-1 B cells and are referred to as non-pathogenic autoantibodies . Phosphorylcholine, also known as choline phosphate or CHOP, belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. The phosphate of choline, and the parent compound of the phosphorylcholine family. Phosphorylcholine exists in all living species, ranging from bacteria to humans. Within humans, phosphorylcholine participates in a number of enzymatic reactions. In particular, phosphorylcholine can be converted into choline through its interaction with the enzyme phosphoethanolamine/phosphocholine phosphatase. In addition, phosphorylcholine can be converted into CDP-choline; which is mediated by the enzyme choline-phosphate cytidylyltransferase a. In humans, phosphorylcholine is involved in phospholipid biosynthesis. Outside of the human body, phosphorylcholine has been detected, but not quantified in several different foods, such as barley, pak choy, black radish, saskatoon berries, and acorns. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID P074

Dihydroxyacetone phosphate

C3H7O6P (169.9980252)

An important intermediate in lipid biosynthesis and in glycolysis.; Dihydroxyacetone phosphate (DHAP) is a biochemical compound involved in many reactions, from the Calvin cycle in plants to the ether-lipid biosynthesis process in Leishmania mexicana. Its major biochemical role is in the glycolysis metabolic pathway. DHAP may be referred to as glycerone phosphate in older texts.; Dihydroxyacetone phosphate lies in the glycolysis metabolic pathway, and is one of the two products of breakdown of fructose 1,6-phosphate, along with glyceraldehyde 3-phosphate. It is rapidly and reversibly isomerised to glyceraldehyde 3-phosphate.; In the Calvin cycle, DHAP is one of the products of the sixfold reduction of 1,3-bisphosphoglycerate by NADPH. It is also used in the synthesis of sedoheptulose 1,7-bisphosphate and fructose 1,6-bisphosphate which are both used to reform ribulose 5-phosphate, the key carbohydrate of the Calvin cycle. Dihydroxyacetone phosphate is found in many foods, some of which are sesame, mexican groundcherry, parsley, and common wheat. [Spectral] Glycerone phosphate (exact mass = 169.99802) and beta-D-Fructose 1,6-bisphosphate (exact mass = 339.99605) and NADP+ (exact mass = 743.07545) 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. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis. Dihydroxyacetone phosphate is found to be associated with transaldolase deficiency, which is an inborn error of metabolism. Dihydroxyacetone phosphate has been identified in the human placenta (PMID: 32033212). KEIO_ID D014

Nadide

[C21H28N7O14P2]+ (664.1169428000001)

[Spectral] NAD+ (exact mass = 663.10912) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Cytidine (exact mass = 243.08552) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] NAD+ (exact mass = 663.10912) and NADP+ (exact mass = 743.07545) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

1,4-Dihydronicotinamide adenine dinucleotide

C21H29N7O14P2 (665.1247674)

Nicotinamide adenine dinucleotide (NAD) is a coenzyme central to metabolism. Found in all living cells, NAD is called a dinucleotide because it consists of two nucleotides joined through their phosphate groups. One nucleotide contains an adenine nucleobase and the other nicotinamide. NAD exists in two forms: an oxidized and reduced form, abbreviated as NAD+ and NADH (H for hydrogen) respectively. NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH. NAD (or nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be either converted into ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it via cellular respiration. NAD is a coenzyme composed of ribosylnicotinamide 5-diphosphate coupled to adenosine 5-phosphate by a pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). NADP is formed through the addition of a phosphate group to the 2 position of the adenosyl nucleotide through an ester linkage. NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5-diphosphate coupled to adenosine 5-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2 position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed) [HMDB]. NADH is found in many foods, some of which are dill, ohelo berry, fox grape, and black-eyed pea. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Quinone

C6H4O2 (108.0211284)

Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world. 1,4-Benzoquinone, commonly known as para-quinone or quinone, is a chemical compound with the formula C6H4O2. 1,4-Benzoquinone is found in barley, olive, and anise. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents

Hydroquinone

C6H6O2 (110.0367776)

Hydroquinone, also benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component in most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver. [HMDB]. Hydroquinone is found in many foods, some of which are kai-lan, agar, red bell pepper, and jostaberry. Hydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver. D020011 - Protective Agents > D011837 - Radiation-Protective Agents D020011 - Protective Agents > D000975 - Antioxidants D009676 - Noxae > D009153 - Mutagens D - Dermatologicals

Palmityl-CoA

C37H66N7O17P3S (1005.3448576)

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

Water

H2O (18.0105642)

Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71\\% of Earths surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the bodys solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the suns energy to split off waters hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the suns energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia). Water, also known as purified water or dihydrogen oxide, is a member of the class of compounds known as homogeneous other non-metal compounds. Homogeneous other non-metal compounds are inorganic non-metallic compounds in which the largest atom belongs to the class of other nonmetals. Water can be found in a number of food items such as caraway, oxheart cabbage, alaska wild rhubarb, and japanese walnut, which makes water a potential biomarker for the consumption of these food products. Water can be found primarily in most biofluids, including ascites Fluid, blood, cerebrospinal fluid (CSF), and lymph, as well as throughout all human tissues. Water exists in all living species, ranging from bacteria to humans. In humans, water is involved in several metabolic pathways, some of which include cardiolipin biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)), cardiolipin biosynthesis cl(i-13:0/i-15:0/i-20:0/i-24:0), cardiolipin biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)), and cardiolipin biosynthesis cl(a-13:0/i-18:0/i-13:0/i-19:0). Water is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis tg(i-21:0/i-13:0/21:0), de novo triacylglycerol biosynthesis tg(22:0/20:0/i-20:0), de novo triacylglycerol biosynthesis tg(a-21:0/i-20:0/i-14:0), and de novo triacylglycerol biosynthesis tg(i-21:0/a-17:0/i-12:0). Water is a drug which is used for diluting or dissolving drugs for intravenous, intramuscular or subcutaneous injection, according to instructions of the manufacturer of the drug to be administered [fda label]. Water plays an important role in the world economy. Approximately 70\\% of the freshwater used by humans goes to agriculture. Fishing in salt and fresh water bodies is a major source of food for many parts of the world. Much of long-distance trade of commodities (such as oil and natural gas) and manufactured products is transported by boats through seas, rivers, lakes, and canals. Large quantities of water, ice, and steam are used for cooling and heating, in industry and homes. Water is an excellent solvent for a wide variety of chemical substances; as such it is widely used in industrial processes, and in cooking and washing. Water is also central to many sports and other forms of entertainment, such as swimming, pleasure boating, boat racing, surfing, sport fishing, and diving .

PA(16:0/16:0)

C35H69O8P (648.4729804)

PA(16:0/16:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-coA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). [HMDB] PA(16:0/16:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-CoA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776).

PC(16:0/16:0)

C40H80NO8P (733.562125)

PC(16:0/16:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC. PC(16:0/16:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Dipalmitoylphosphatidylcholine (DPPC) is the major constituent of pulmonary surfactant. It is also used for research purposes in studying liposomes, lipid bilayers, and model biological membranes. R - Respiratory system > R07 - Other respiratory system products > R07A - Other respiratory system products > R07AA - Lung surfactants C78273 - Agent Affecting Respiratory System DPPC (129Y83) is a zwitterionic phosphoglyceride that can be used for the preparation of liposomal monolayers[1]. DPPC-liposome serves effectively as a delivery vehicle for inducing immune responses against GSL antigen in mice[2].

PE(16:0/16:0)

C37H74NO8P (691.5151774)

PE(16:0/16:0) is a phosphatidylethanolamine (PE or GPEtn). It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PE(16:0/16:0), in particular, consists of two chains of palmitic acid at the C-1 and C-2 positions. The palmitic acid moieties are derived from fish oils, milk fats, vegetable oils and animal fats. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. PE(16:0/16:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. D006401 - Hematologic Agents > D010975 - Platelet Aggregation Inhibitors

LysoPC(16:0/0:0)

C24H50NO7P (495.33247200000005)

LysoPC(16:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-Rs are members of the G protein-coupled receptor family of integral membrane proteins. [HMDB] LysoPC(16:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-Rs are members of the G protein-coupled receptor family of integral membrane proteins.

CDP-DG(16:0/16:0)

C44H81N3O15P2 (953.5142656)

CDP-DG(16:0/16:0) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05\\% or so of the total phospholipids. [HMDB] CDP-DG(16:0/16:0) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05\\% or so of the total phospholipids.

PGP(16:0/16:0)

C38H76O13P2 (802.4760906)

PGP(16:0/16:0) is a phosphatidylglycerolphosphate or glycerophospholipid (PGP or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidylglycerolphosphate is present at a level of 1-2\\% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11\\% of the total. It is well established that the concentration of Phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1-sn-glycerol 3-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGPs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PGP also serves as a precursor for the synthesis of cardiolipin. PGP is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. PGP(16:0/16:0) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.

Citicoline

C14H26N4O11P2 (488.10732659999996)

CDP-choline is a member of the class of phosphocholines that is the chloine ester of CDP. It is an intermediate obtained in the biosynthetic pathway of structural phospholipids in cell membranes. It has a role as a human metabolite, a psychotropic drug, a neuroprotective agent, a Saccharomyces cerevisiae metabolite and a mouse metabolite. It is a member of phosphocholines and a member of nucleotide-(amino alcohol)s. It is functionally related to a CDP. It is a conjugate base of a CDP-choline(1+). Citicoline is a donor of choline in biosynthesis of choline-containing phosphoglycerides. It has been investigated for the treatment, supportive care, and diagnosis of Mania, Stroke, Hypomania, Cocaine Abuse, and Bipolar Disorder, among others. Citicoline is a nutritional supplement and source of choline and cytidine with potential neuroprotective and nootropic activity. Citicoline, also known as cytidine-5-diphosphocholine or CDP-choline, is hydrolyzed into cytidine and choline in the intestine. Following absorption, both cytidine and choline are dispersed, utilized in various biosynthesis pathways, and cross the blood-brain barrier for resynthesis into citicoline in the brain, which is the rate-limiting product in the synthesis of phosphatidylcholine. This agent also increases acetylcholine (Ach), norepinephrine (NE) and dopamine levels in the central nervous system (CNS). In addition, citicoline is involved in the preservation of sphingomyelin and cardiolipin and the restoration of Na+/K+-ATPase activity. Citicoline also increases glutathione synthesis and glutathione reductase activity, and exerts antiapoptotic effects. Donor of choline in biosynthesis of choline-containing phosphoglycerides. N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics D002491 - Central Nervous System Agents > D018697 - Nootropic Agents Citicoline (Cytidine diphosphate-choline) is an intermediate in the synthesis of phosphatidylcholine, a component of cell membranes. Citicoline exerts neuroprotective effects. Citicoline (Cytidine diphosphate-choline) is an intermediate in the synthesis of phosphatidylcholine, a component of cell membranes. Citicoline exerts neuroprotective effects.

PI 32:0

C41H79O13P (810.5258014)

Found in mouse muscle; TwoDicalId=438; MgfFile=160824_Muscle_EPA_Neg_07; MgfId=499 Found in mouse kidney; TwoDicalId=164; MgfFile=160827_Kidney_AA_Neg_18; MgfId=910

UNII:R7P33H2T7C

C35H68O5 (568.5066478)

A 1,2-diacyl-sn-glycerol in which both acyl groups are specified as palmitoyl (hexadecanoyl). 1,2-Dipalmitoyl-sn-glycerol is an endogenous metabolite.

PS(32:0)

C38H74NO10P (735.5050074)

(2R)-2-hydroxy-3-(phosphonooxy)propyl hexadecanoate

C19H39O7P (410.2433274)

1,2-Dipalmitoyl-phosphatidyl-glycerole

C38H75O10P (722.509758)

D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D001430 - Bacteriocins

Phosphate Ion

O4P-3 (94.953423)

CL(16:0/16:0/16:0/16:0)

C73H142O17P2 (1352.9721742)

CL(16:0/16:0/16:0/16:0) is a cardiolipin (CL). Cardiolipins are sometimes called double phospholipids because they have four fatty acid tails, instead of the usual two. They are glycerophospholipids in which the O1 and O3 oxygen atoms of the central glycerol moiety are each linked to one 1,3-diacylglyerol chain. Their general formula is OC(COP(O)(=O)OC[C@@H](CO[R1])O[R2])COP(O)(=O)OC[C@@H](CO[R3])O[R4], where R1-R4 are four fatty acyl chains. CL(16:0/16:0/16:0/16:0) contains four chains of hexadecanoic acid at the C1, C2, C3 and C4 positions fatty acids. Cardiolipins are known to be present in all mammalian cells, especially cells with a high number of mitochondria. De novo synthesis of Cardiolipins begins with condensing phosphatidic acid (PA) with cytidine-5’-triphosphate (CTP) to form cytidine-diphosphate-1,2-diacyl-sn-glycerol (CDP-DG). Glycerol-3-phosphate is subsequently added to this newly formed CDP-DG molecule to form phosphatidylglycerol phosphate (PGP), which is immediately dephosphorylated to form PG. The final step is the process of condensing the PG molecule with another CDP-DG molecule to form a new cardiolipin, which is catalyzed by cardiolipin synthase. All new cardiolipins immediately undergo a series remodeling resulting in the common cardiolipin compositions. (PMID: 16442164). Cardiolipin synthase shows no selectivity for fatty acyl chains used in the de novo synthesis of cardiolipin (PMID: 16442164). Cardiolipins (bisphosphatidyl glycerol) are an important component of the inner mitochondrial membrane, where they constitute about 20\\% of the total lipid. While most lipids are made in the endoplasmic reticulum, cardiolipin is synthesized on the matrix side of the inner mitochondrial membrane and are important for mitochondrial respiratory capacity. They are highly abundant in metabolically active cells (heart, muscle) and play an important role in the blood clotting process. Tafazzin is an important enzyme in the remodeling of cardiolipins, and in contrast to cardiolipin synthase, it shows strong acyl specificity. This suggests that the specificity in cardiolipin composition is achieved through the remodeling steps. Mutation in the tafazzin gene disrupts the remodeling of cardiolipins and is the cause of Barth syndrome (BTHS), an X-linked human disease (PMID: 16973164). BTHS patients seem to lack acyl specificity. As a result, there are many potential cardiolipin species that can exist (PMID: 16226238).

1-Palmitoyl-sn-glycero-3-phosphoethanolamine

C21H44NO7P (453.28552440000004)