88165PathwayPlasmalogen SynthesisPlasmalogens are a class of phospholipids found in animals. Plasmalogens are thought to influence membrane dynamics and fatty acid levels, while also having roles in intracellular signalling and as antioxidants. Plasmalogens consist of a glycerol backbone with an vinyl-ether-linked alkyl chain at the sn-1 position, an ester-linked long-chain fatty acid at the sn-2 position, and a head group attached to the sn-3 position through a phosphodiester linkage. It is the vinyl-ether-linkage that separates plasmalogens from other phospholipids. Plasmalogen biosynthesis begins in the peroxisomes, where the integral membrane protein dihydroxyacetone phosphate acyltransferase (DHAPAT) catalyzes the esterification of the free hydroxyl group of dihydroxyacetone phosphate (DHAP) with a molecule any of long chain acyl CoA. Next, alkyl-DHAP synthase, a peroxisomal enzyme associated with DHAPAT, replaces the fatty acid on the DHAP with a long chain fatty alcohol. The third step of plasmalogen biosynthesis is catalyzed by the enzyme acyl/alkyl-DHAP reductase, which is found in the membrane of both the peroxisome and endoplasmic reticulum (ER). Acyl/alkyl-DHAP reductase uses NADPH as a cofactor to reduce the ketone of the 1-alkyl-DHAP using a classical hydride transfer mechanism. The remainder of plasmalogen synthesis occurs using enzymes in the ER. Lysophosphatidate acyltransferases (LPA-ATs) transfer the acyl component of a polyunsaturated acyl-CoA to the the 1-alkyl-DHAP, creating a 1-alkyl-2-acylglycerol 3-phosphate. The phosphate is then removed by lipid phosphate phosphohydrolase I (PAP-I), and the head group is attached by a choline/ethanolaminephosphotransferase. The majority of plasmalogens have either ethanolamine or choline as a headgroup, although a small amount of serine and inositol-linked ether-phospholipids can also be found. In the final step, the vinyl-ether linkage is created by plasmanylethanolamine desaturase, which catalyzes the formation of a double bond in the alkyl chain of the plasmalogen. MetabolicPW088283CenterPathwayVisualizationContext8855929002200#000099PathwayVisualization8803988165Plasmalogen SynthesisPlasmalogens are a class of phospholipids found in animals. Plasmalogens are thought to influence membrane dynamics and fatty acid levels, while also having roles in intracellular signalling and as antioxidants. Plasmalogens consist of a glycerol backbone with an vinyl-ether-linked alkyl chain at the sn-1 position, an ester-linked long-chain fatty acid at the sn-2 position, and a head group attached to the sn-3 position through a phosphodiester linkage. It is the vinyl-ether-linkage that separates plasmalogens from other phospholipids. Plasmalogen biosynthesis begins in the peroxisomes, where the integral membrane protein dihydroxyacetone phosphate acyltransferase (DHAPAT) catalyzes the esterification of the free hydroxyl group of dihydroxyacetone phosphate (DHAP) with a molecule any of long chain acyl CoA. Next, alkyl-DHAP synthase, a peroxisomal enzyme associated with DHAPAT, replaces the fatty acid on the DHAP with a long chain fatty alcohol. The third step of plasmalogen biosynthesis is catalyzed by the enzyme acyl/alkyl-DHAP reductase, which is found in the membrane of both the peroxisome and endoplasmic reticulum (ER). Acyl/alkyl-DHAP reductase uses NADPH as a cofactor to reduce the ketone of the 1-alkyl-DHAP using a classical hydride transfer mechanism. The remainder of plasmalogen synthesis occurs using enzymes in the ER. Lysophosphatidate acyltransferases (LPA-ATs) transfer the acyl component of a polyunsaturated acyl-CoA to the the 1-alkyl-DHAP, creating a 1-alkyl-2-acylglycerol 3-phosphate. The phosphate is then removed by lipid phosphate phosphohydrolase I (PAP-I), and the head group is attached by a choline/ethanolaminephosphotransferase. The majority of plasmalogens have either ethanolamine or choline as a headgroup, although a small amount of serine and inositol-linked ether-phospholipids can also be found. In the final step, the vinyl-ether linkage is created by plasmanylethanolamine desaturase, which catalyzes the formation of a double bond in the alkyl chain of the plasmalogen. Metabolic51CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000662Platelet CL:00002331Homo sapiens9606EukaryoteHuman12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle4Arabidopsis thaliana3702EukaryoteThale cress6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast23Pseudomonas aeruginosa287Prokaryote21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia449Bathymodiolus platifrons220390EukaryoteDeep sea mussel2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast4PeroxisomeGO:00057777Endoplasmic Reticulum MembraneGO:000578914Mitochondrial Outer MembraneGO:00057415CytoplasmGO:00057371CytosolGO:000582924Mitochondrial Intermembrane SpaceGO:00057583Mitochondrial MatrixGO:00057592MitochondrionGO:000573912Mitochondrial Inner MembraneGO:000574327Peroxisome MembraneGO:00057788Smooth Endoplasmic Reticulum GO:000579013Endoplasmic ReticulumGO:000578310Cell MembraneGO:00058866LysosomeGO:000576416Lysosomal LumenGO:004320220Endoplasmic Reticulum LumenGO:000578831Periplasmic SpaceGO:000562035ChloroplastGO:000950734Plant-Type VacuoleGO:000032539Mitochondrial membraneGO:003196611Extracellular SpaceGO:000561518Melanosome MembraneGO:003316225Golgi apparatusGO:000579421SynapseGO:004520215NucleusGO:000563436MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016840PeriplasmGO:004259719sarcoplasmic reticulumGO:001652932Inner MembraneGO:007025826Golgi apparatus membraneGO:00001391LiverBTO:00007597294Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273102Endothelium BTO:00003935cardiocyteBTO:00015395411PW_BS00000549711PW_BS000049221411PW_BS0000223344121PW_BS0000283317121PW_BS00002832914121PW_BS000028383751PW_BS0001003821451PW_BS0001002881441PW_BS0000243891461PW_BS000112390761PW_BS000112408451PW_BS0001153744171PW_BS0000534824101PW_BS000115502461PW_BS0001153987171PW_BS0001138511PW_BS0000082111PW_BS000002422411PW_BS00004210813PW_BS0001081471241PW_BS000147151141PW_BS0001511601181PW_BS000160315123PW_BS0000241321121PW_BS0001321115121PW_BS00011134524121PW_BS000028124151PW_BS000124388161PW_BS0001121181171PW_BS000118122551PW_BS0001224182451PW_BS0001151355171PW_BS00013545424171PW_BS0001152975101PW_BS0000242991101PW_BS00002448924101PW_BS000115205561PW_BS0000245062461PW_BS0001154311PW_BS0000043211PW_BS000003171211PW_BS000017592711PW_BS00005929111PW_BS000029311511PW_BS000031111811PW_BS000011181311PW_BS000018101711PW_BS0000105811411PW_BS00005814101PW_BS000014541315PW_BS0000546131PW_BS0000061021231PW_BS0001021041431PW_BS000104103331PW_BS000103101531PW_BS0001011553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS00017816212181PW_BS00016219914181PW_BS000024188118PW_BS0000241632181PW_BS0001631985181PW_BS00002421013181PW_BS000024222341PW_BS000024226441PW_BS000024224241PW_BS00002417018PW_BS0001701951318PW_BS0000242491341PW_BS00002429341PW_BS0000241333121PW_BS00013313412121PW_BS0001341122121PW_BS0001123361121PW_BS00002812915121PW_BS0001291151012PW_BS00011533217121PW_BS000028350114121PW_BS00002833527121PW_BS00002813013121PW_BS0001303331212PW_BS0000283683601PW_BS0000281192171PW_BS0001193761017PW_BS00005339914171PW_BS000113406351PW_BS000115405105PW_BS0001153841251PW_BS000100407251PW_BS000115117131PW_BS0001171231751PW_BS00012343311451PW_BS0001151251351PW_BS000125429151PW_BS0001154141551PW_BS0001154222751PW_BS0001151203171PW_BS00012012112171PW_BS00012144717171PW_BS000115468114171PW_BS00011513613171PW_BS0001364641171PW_BS00011545015171PW_BS00011537527171PW_BS0000534793101PW_BS0001154781010PW_BS00011548012101PW_BS00011548414101PW_BS0001154812101PW_BS00011549127101PW_BS00011530013101PW_BS000024501361PW_BS000115209106PW_BS0000243911261PW_BS000112206261PW_BS0000245082761PW_BS0001153951361PW_BS0001139611PW_BS0000092811611PW_BS000028261115PW_BS0000263612011PW_BS00003613121PW_BS000013126651PW_BS00012612711651PW_BS00012715612241PW_BS00015617912211PW_BS000179107313PW_BS0001072137181PW_BS0000242231241PW_BS0000242164181PW_BS0000242156181PW_BS0000242111018PW_BS0000242253541PW_BS0000242273441PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000243183123PW_BS0000241136121PW_BS000113337116121PW_BS0000283583912PW_BS00002836912601PW_BS0000284436171PW_BS000115448116171PW_BS000115207661PW_BS00002415111PW_BS000015204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100943PW_BS000094105113PW_BS000105110231PW_BS0001101141112PW_BS000114140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS0000951572241PW_BS00015715924PW_BS00015916611PW_BS0001661802211PW_BS00018015284PW_BS00015221425181PW_BS00002421217181PW_BS0000241901118PW_BS0000242771218PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS00002465111PW_BS0000652905491PW_BS00002429817101PW_BS0000242941141PW_BS0000243081011PW_BS0000243221231PW_BS000024253541PW_BS00002434141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115409115PW_BS0001154151851PW_BS0001154251355PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS0001154461217PW_BS0001151371117PW_BS00013745118171PW_BS00011546013175PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154831110PW_BS00011548718101PW_BS00011549025101PW_BS0001154957101PW_BS000115208116PW_BS0000245041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS000047231511PW_BS000023241529PW_BS00002425715291PW_BS00002430412PW_BS000024109323PW_BS000109562611PW_BS00005616212PW_BS000016397113PW_BS000039215114PW_BS000021918511PW_BS000091184121PW_BS000024372102PW_BS0000285181PW_BS0000512111Eicosanoyl-CoAHMDB0004258Eicosanoyl-CoA is an intermediate metabolite in the synthesis of phosphatidic acid, a substrate of lysophosphatidic acid acyltransferase with high specificity as an acyl donor. Cells and membranes of mammalian cells synthesize their glycerophospholipids and triglycerides to maintain the cellular integrity and to provide energy for cellular functions. The phospholipids are synthesized de novo in cells through an evolutionary conserved process involving serial acylations of glycerol-3-phosphate. Several isoforms of the enzyme 1-acylglycerol-3-phosphate-O-acyltransferase (EC 2.3.1.51, AGPAT) acylate lysophosphatidic acid at the sn-2 position to produce phosphatidic acid. Bile acid-CoA:amino acid N-acyltransferase (EC 2.3.1.65, BACAT) catalyzes the conjugation of bile acids to glycine and taurine for excretion into bile and can utilize Eicosanoyl-CoA as an acyl donor as well; this may play important roles in protection against toxicity by accumulation of unconjugated bile acids and non-esterified very long-chain fatty acids. (PMID: 17535882, 12810727).15895-27-9C020411606115115527ICOSANOYL-COA17220830CCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC41H74N7O17P3SInChI=1S/C41H74N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h28-30,34-36,40,51-52H,4-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/t30-,34-,35-,36+,40-/m1/s1JYLSVNBJLYCSSW-IBYUJNRCSA-N{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-[(2-{[2-(icosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid1062.061061.407476119-3.349[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-3-[(2-{[2-(icosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid0-4FDB023354Arachidinoyl-coa;Arachidinoyl-coenzyme a;Arachidoyl coenzyme a;Arachidoyl-coa;Arachidoyl-coenzyme a;Arachidyl coa;Arachidyl coenzyme a;Eicosanethioate;Eicosanethioic acid;Eicosanethioic acid s-ester with coenzyme a;Eicosanoyl coenzyme a;Eicosyl-coenzyme a;Icosanoyl-coa;S-eicosanoate;S-eicosanoate coa;S-eicosanoate coenzyme a;S-eicosanoic acid;CoA(20:0)PW_C002111Eicosan330852550649255822278558334818643318610832995724383998853821090342881116473891142233901225894081251613741267354821283295021288653981134Dihydroxyacetone phosphateHMDB0001473Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.57-04-5C0011166816108DIHYDROXY-ACETONE-PHOSPHATE648DB04326OCC(=O)COP(O)(O)=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)GNGACRATGGDKBX-UHFFFAOYSA-N(3-hydroxy-2-oxopropoxy)phosphonic acid170.0578169.998024468-0.893dihydroxyacetone-phosphate0-2FDB0016181,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acidPW_C001134Dhapp10268147423305542534258131085908147593615168841604266031577098132779341117837434578559334938241241105513881158391181207331221225644181225904081233331351251374541251623741257872971259502991267124891267364821272422051283035061283305026772DHAP(18:0)HMDB0011133DHAP(18:0) is the octadecanoyl derivative of dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia)C0380544012736476389126CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=OC21H41O7PInChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26)GTPATKZCXDKGQS-UHFFFAOYSA-N[3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid436.5198436.258990178-5.712stearoylglycerone phosphate0-2C038051-octadecanoyl dhap;1-octadecanoyl dihydroxyacetone phosphate;1-octadecanoyl-glycerone-3-phosphate;1-stearoylglycerone 3-phosphatePW_C006772DP18:033095785603341225914081251633741267374821283315021099Coenzyme AHMDB0001423Coenzyme 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).85-61-0C0001068161146900CO-A6557CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC21H36N7O16P3SInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1RGJOEKWQDUBAIZ-IBOSZNHHSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid767.534767.115208365-2.2210coenzyme A0-4FDB022614Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatePW_C001099CoA2114386884538792289217240759241422459528132928623133421133511846181046295848421448655448796523210252471045280103547712457341085777101602315560751616384164681786930160696116269731997083188710816372931987347210745822282291519081226909022491241709215195130132991531824925488494261631576907293771191337722213477230329772921117755013277555334775631127763333677672129779961157804733278056350784133357856713079259333799743318000536880620118806273748063511980665376938283829383438398674288110555389110561390115842399115847398119951406120147405120231384120305122120634407120762117121406123121421433121521125121666429121682408121714414122404422122741120122904121122960135123965447123979468124079136124220464124265450124974375125341479125509478125579480125592484125634297126084481126549491126560482126746300126884501127046209127109391127301205127540206127667388128121508128133502128340395964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)CO[P@](O)(=O)O[P@@](O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid785.5497785.157134455-2.279flavine-adenine dinucleotide0-3FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD99911451868192321642531762828825188402118814148942161229162249213358253622372326460236468831474113475810488165268103528510253351115496126551112756131186030155605415660821616116162639016475178649917966661077039163717520573212137465222748722390762241181821611887215118992111229622512328249124431511251922712595226127102911272029213029301130413024362331877080293771261337715213477501113775071127751811577541334776151327772633778054329783753457893033179222336792723588001236880034369807141191199584061199993841200514081201074071204324051204531221204901241212784291212984181214173821214893831227481201227761211228023741228234431230663761230871351231664481238494641238684541239763991240473981253484791253784801254294821254744811256972971259794891261072991262774841268915011269203911269685021269872071270112061273102091274325061276023881278403891584OctadecanolHMDB0002350Octadenol is a fatty alcohol present in human and is normally incorporated into plasmalogen lipids. Patients with the autosomal recessive form of rhizomelic chondrodysplasia punctata (AR-RCDP) have elevated octadenol levels, but tended to be normal in other generalized peroxisomal disorders such as neonatal adrenoleukodystrophy and Zellweger syndrome (peroxisomal disorders are deficient in the incorporation of fatty alcohol into plasmalogen lipids). (PMID: 8373640). Sjogren-Larsson syndrome is defined by the triad of ichthyosis, mental retardation, and spasticity, and patients accumulate fatty alcohols such as Octadenol in the plasma and cultured fibroblasts. (PMID: 2241202). Sjogren-Larsson syndrome (SLS) is an autosomal recessive disorder associated with reduced activity of the fatty alcohol: NAD+ oxidoreductase complex (FAO). SLS patients are specifically deficient in the fatty aldehyde dehydrogenase (FALDH) component of FAO. Measurement of FAO and FALDH detection for SLS, FAO and FALDH activities in cultured skin fibroblasts using the 18-carbon substrate Octadenol is useful for SLS carrier detection. (PMID: 1583866). Patients with Sjogren-Larsson syndrome accumulate long-chain fatty alcohol in plasma, with a greater relative accumulation of Octadenol. (PMID: 2666627).112-92-5D01924822132154CYCLOHEXANOL7928CCCCCCCCCCCCCCCCCCOC18H38OInChI=1S/C18H38O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h19H,2-18H2,1H3GLDOVTGHNKAZLK-UHFFFAOYSA-Noctadecan-1-ol270.4937270.292265838-6.711stearyl alcohol00FDB0127641-hydroxyoctadecane;Alcohol stearylicus;Alfol 18;Atalco s;N-1-octadecanol;N-octadecanol;N-octadecyl alcohol;Octadecan-1-ol;Octadecanol nf;Octadecyl alcohol;Stearal;Stearic alcohol;Stearol;Stearyl alcohol;Stearyl alcohol pure;1-octadecanol;Octadecanol;StearylalkoholPW_C001584Stearal33135785613341225944081251663741267404821283345026778DHAP(18:0e)HMDB0011142DHAP(18:0e) is the octadecanoyl derivative of Dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0e) or 1-Octadecyl-glycerone-3-phosphate is converted from 1-Octadecanoyl-glycerone-3-phosphate via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. (Wikipedia).497917567816325996866CCCCCCCCCCCCCCCCCCOCC(=O)COP(O)(O)=OC21H43O6PInChI=1S/C21H43O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h2-20H2,1H3,(H2,23,24,25)DSLZSTBYLRGPIK-UHFFFAOYSA-N[3-(octadecyloxy)-2-oxopropoxy]phosphonic acid422.5363422.27972562-5.5223-(octadecyloxy)-2-oxopropoxyphosphonic acid0-21-octadecyl dhap;1-octadecyl dihdroxyacetone phosphate;1-octadecyl-glycerone-3-phosphatePW_C006778DP18:0e331453318187856233478575130122595408122607125125167374125179136126741482126755300128335502128349395661Stearic acidHMDB0000827Stearic acid, also called octadecanoic acid, is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. It is a waxy solid, and its chemical formula is CH3(CH2)16COOH. Its name comes from the Greek word stear, which means tallow. Its IUPAC name is octadecanoic acid. -- Wikipedia.57-11-4C01530528128842STEARIC_ACID5091DB03193CCCCCCCCCCCCCCCCCC(O)=OC18H36O2InChI=1S/C18H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-17H2,1H3,(H,19,20)QIQXTHQIDYTFRH-UHFFFAOYSA-Noctadecanoic acid284.4772284.271530396-6.631stearic acid0-1FDB0029411-heptadecanecarboxylate;1-heptadecanecarboxylic acid;N-octadecanoate;N-octadecanoic acid;Octadecanoate;Octadecanoic acid;Stearate;Stearex beads;Stearic acid;Stearic acid cherry;Stearophanate;Stearophanic acid;FA(18:0)PW_C00066118:02884222890833155129281511297922678342111785633341225964081226191221251683741251931351267424821267712971283365021283662056780LPA(18:0e/0:0)HMDB00111441-Octadecyl-sn-glycero-3-phosphate is a lysophosphatidyl ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. The formation of the ether bond in mammals requires two enzymes, dihydoxyacetonephosphate acyltransferase (DHAPAT) and alkyldihydroxyacetonephosphate synthase (ADAPS), that reside in the peroxisome.104324938607920CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=OC21H45O6PInChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)HUUYDUFSUADEJQ-UHFFFAOYSA-N[2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid424.559424.295376167-5.2532-hydroxy-3-(octadecyloxy)propoxyphosphonic acid0-21-octadecyl-sn-glycero-3-phosphate;Lysopa(18:0e);Lysopa(o-18:0);Pa(o-18:0/0:0);[(2r)-2-hydroxy-3-octadecoxy-propyl] dihydrogen phosphatePW_C006780LPA18333911334818785641301225971251251691361267433001283373952791Arachidonyl-CoAHMDB0006523Arachidonyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. Arachidonyl-CoA is produced from 8,11,14-Eicosatrienoyl-CoA via the enzyme fatty acid desaturase 1 (EC 1.14.19.-). It is then converted to Arachidonic acid via the enzymepalmitoyl-CoA hydrolase (EC 3.1.2.2).17046-56-9C022491606115215514ARACHIDONYL-COA17220831CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2NC41H66N7O17P3SInChI=1S/C41H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h8-9,11-12,14-15,17-18,28-30,34-36,40,51-52H,4-7,10,13,16,19-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b9-8-,12-11-,15-14-,18-17-/t30-,34?,35+,36+,40-/m1/s1JDEPVTUUCBFJIW-BSQIERQBSA-N{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid1053.9861053.344873947-3.379[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid0-4FDB023958(5z,8z,11z,14z)-icosatetraenoyl-coa;(5z,8z,11z,14z)-icosatetraenoyl-coenzyme a;Arachidonoyl-coa;Arachidonoyl-coenzyme a;Arachidonyl-coa;Arachidonyl-coenzyme a;CoA(20:4(5Z,8Z,11Z,14Z))PW_C002791AracCoA3349182551649256802278565130818743318689232995734383100655382111742389114229390122598125125170136126744300128338395128875398404821-alkyl-2-acylglycerol 3 phosphate(18:0/20:4)HMDB0061332[(2R)-2-[(5E,8E,11E,14E)-Icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphonic acid belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphates. These are glycerophosphates in which the O-1 atom of the glycerol is bonded to a fatty acid (saturated or unsaturated) through an ether linkage, and the O-2 atom is bonded to another fatty acid through an ester linkage. [(2R)-2-[(5E,8E,11E,14E)-Icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphonic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.CCCCCCCCCCCCCCCCCCOC[C@H](COP(O)(O)=O)OC(=O)CCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC41H75O7PInChI=1S/C41H75O7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-41(42)48-40(39-47-49(43,44)45)38-46-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,40H,3-10,12,14-16,18,20-21,23,25-27,29,31-39H2,1-2H3,(H2,43,44,45)/b13-11+,19-17+,24-22+,30-28+/t40-/m1/s1VYWAINFTJJSWHG-WMPKNLFQSA-N[(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphonic acid711.0038710.525041266-7.122(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxyphosphonic acid0-2PW_C0404821A2A3PP334111335018785661301225991251251711361267453001283393951420WaterHMDB0002111Water 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 Earth's 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 body's 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 sun's energy to split off water's 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 sun's 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).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513404861-alkyl-2-acylglycerolHMDB0061333(2S)-1-Hydroxy-3-(octadecyloxy)propan-2-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate belongs to the class of organic compounds known as 1-alkyl,2-acylglycerols. These are glycerides consisting of two fatty acyl chains covalently bonded to a glycerol molecule at the 1- and 2-positions through an ether and an ester linkage, respectively (2S)-1-Hydroxy-3-(octadecyloxy)propan-2-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate is considered to be a practically insoluble (in water) and relatively neutral molecule.CCCCCCCCCCCCCCCCCCOC[C@H](CO)OC(=O)CCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC41H74O4InChI=1S/C41H74O4/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-41(43)45-40(38-42)39-44-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,40,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-39H2,1-2H3/b13-11+,19-17+,24-22+,30-28+/t40-/m0/s1ZZXSPACFFRFTBX-IFUORAJTSA-N(2S)-1-hydroxy-3-(octadecyloxy)propan-2-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate631.0239630.558710856-7.721(2S)-1-hydroxy-3-(octadecyloxy)propan-2-yl (5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoate00PW_C0404861A2A337818785691301226011251251731361267483001283423951104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153891201CDP-EthanolamineHMDB0001564Cytidine is a molecule (known as a nucleoside) that is formed when cytosine is attached to a ribose ring (also known as a ribofuranose) via a beta-N1-glycosidic bond. CDP-Ethanolamine has the chemical formula C11H20N4O11P2, and an average molecular weight of 446.2442. CDP-Ethanolamine is involved in multiple pathways, some of which are Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) Pathway, Phosphatidylcholine Biosynthesis PC(20:3(8Z,11Z,14Z)/22:4(7Z,10Z,13Z,16Z)) Pathway, Phosphatidylethanolamine Biosynthesis PE(20:1(11Z)/22:0) Pathway, and Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Pathway.3036-18-8C0057012372716732CDP-ETHANOLAMINE110296NCCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=OC11H20N4O11P2InChI=1S/C11H20N4O11P2/c12-2-4-23-27(19,20)26-28(21,22)24-5-6-8(16)9(17)10(25-6)15-3-1-7(13)14-11(15)18/h1,3,6,8-10,16-17H,2,4-5,12H2,(H,19,20)(H,21,22)(H2,13,14,18)/t6-,8-,9-,10-/m1/s1WVIMUEUQJFPNDK-PEBGCTIMSA-N[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](2-aminoethoxy)phosphinic acid446.2442446.060380526-1.536cdp ethanolamine0-1FDB022691Cdp ethanolamine;Cdp-ethanolamine;Cdpethanolamine;Cytidine diphosphate ethanolamine;Cytidine 5'-(trihydrogen diphosphate), p'-(2-aminoethyl) esterPW_C001201C-Etala33841815290288153432240895497857113079966329799783319482038294856383113276389115533399115749398122603125125175136126750300128344395404871-alkyl-2-acylglycerol 3 phosphoethanolamine(18:0/20:4)HMDB0061334(2-Aminoethoxy)[(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphinic acid belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position (2-Aminoethoxy)[(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphinic acid is considered to be a practically insoluble (in water) and relatively neutral molecule.CCCCCCCCCCCCCCCCCCOC[C@H](COP(O)(=O)OCCN)OC(=O)CCC\C=C\C\C=C\C\C=C\C\C=C\CCCCCC43H80NO7PInChI=1S/C43H80NO7P/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-43(45)51-42(41-50-52(46,47)49-39-37-44)40-48-38-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-41,44H2,1-2H3,(H,46,47)/b13-11+,19-17+,24-22+,30-28+/t42-/m1/s1LRBBGQHIVCMVRY-NMJNNTAZSA-N(2-aminoethoxy)[(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxy]phosphinic acid754.0716753.567240431-7.0622-aminoethoxy(2R)-2-[(5E,8E,11E,14E)-icosa-5,8,11,14-tetraenoyloxy]-3-(octadecyloxy)propoxyphosphinic acid00PW_C0404871A2A3PE3385187857213012260412512517613612675130012834539564Cytidine monophosphateHMDB0000095Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].63-37-6C00055613117361CMP5901NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC9H14N3O8PInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1IERHLVCPSMICTF-XVFCMESISA-N{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid323.1965323.051850951-1.305cytidine monophosphate0-2FDB0118825'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acidPW_C000064CMP1151825121427342338618497256576810158021087079188759516091472499151224925719512196164122101511527428515336308153734934815174265231578449111784881157857313078736132799531347996933180421170947913849482138398680223110637391113277390115535398120855122121346121122216124122487405122605125123435135124768118125053376125177136125841297126378299126641478126752300127293205127940388128217209128346395423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+8682274268164762727268115819188832293639983399221116746148349152943176414212410241159294223312629337374540314774914869544974565253104532911153561125376103590614759341516038155609416162501666484178659416468811606979199717020571942067227213723321172502147310216731319874732221176313211843210123122251232424912513288125812261272929015275285153373087713713377236329779373367839333478417335784891157852233178536356785741308002036880045184800483728062311880654135808651580965253818415193832383949002710859622311055939011568739811997440612007012212024738212070240712098140812118112412126542912131941912192412512208640512240842212275912012292139912330711912354637412383546412388945512447713612463737612497837512544729712559848412566947912577748112592148212594729912597349512600049012624347812655349112675330012712538912716450112738050212740738812745150712780420912812550812834739514738Dihydroxyacetone phosphate acyltransferaseA4IF87GNPAT52.3.1.429382938212259240815798D-2-hydroxyglutarate dehydrogenase, mitochondrialA5PKH4
Catalyzes the oxidation of D-2-hydroxyglutarate to alpha-ketoglutarate.
D2HGDH51.1.99.-120879407122593408162051-acyl-sn-glycerol-3-phosphate acyltransferase alphaQ95MP8
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
AGPAT152.3.1.5112129138312130441812140812312141312412142243312260012516258Phospholipid phosphatase 2Q2HJ61
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P) (By similarity).
PLPP253.1.3.412132340512141012312142438212260212514744Cholinephosphotransferase 1Q1LZE6
Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes (By similarity).
CHPT152.7.8.21213204191226061258792Dihydroxyacetone phosphate acyltransferase and Alkyldihydroxyacetonephosphate synthase5PW_P008792170311473821703215798184481-acyl-sn-glycerol-3-phosphate acyltransferase alpha5PW_P00844816665162058460Lipid phosphate phosphohydrolase 15PW_P00846016677162588793Choline/ethanolaminephosphotransferase 15PW_P00879317033147441146942falsePW_R146942Right54764521111Compoundfalse54764611341Compoundtrue54764767721Compoundfalse54764810991Compoundtrue13710387922.3.1.42146943falsePW_R146943Right54764967721Compoundfalse54765015841Compoundtrue54765167781Compoundfalse5476526611Compoundtrue13710487922.3.1.42146944falsePW_R146944Right54765367801Compoundfalse54765427911Compoundtrue547655404821Compoundfalse54765610991Compoundtrue13710584482.3.1.51146945falsePW_R146945Right547657404821Compoundfalse54765814201Compoundtrue547659404861Compoundfalse54766011041Compoundtrue13710684603.1.3.4146946falsePW_R146946Right547661404861Compoundfalse54766212011Compoundtrue547663404871Compoundfalse547664641Compoundtrue13710787937966PW_T007966821867781Compound408125Right2658293211140881false32053010regular2001902658294113440881false54565510regular2001902658295677240881false325105510regular2001902658296109940885false53099510regular503026582979644089false29590010regular100252658298158440881false550114510regular2001902658299677840881false325151510regular200190265830066140881false550141010regular20019026583019644089false290138010regular100252658302678012581false1170188010regular2001902658303279112582false1650174510regular30028026583044048212581false1170138010regular2002002658305109912585false1375159510regular50302658306142012549false1660155010regular787826583074048612581false1705112810regular2001902658308110412546false1678134610regular44432658309120112581false1495101310regular20019026583104048712581false170564310regular20020026583116412581false149576810regular20019026583124231259false181595810regular100252658313677812581false1165233510regular200190928731147384086false3258258subunitregular1608092873215798408113false3458508subunitregular16080928733147384086false31013158subunitregular1608092873415798408113false34513308subunitregular16080928735162051252false119517128subunitregular15070928736162581252false173014308subunitregular15070928737147441252false17309688subunitregular150707932598792880394089252169287319252179287323241326582973620217Cofactor7932608792880394089252189287339252199287343241426583013620222Cofactor7932618448880391259252209287357932628460880391259252219287367932638793880391259252229287373241526583123620235Cofactor3620213M420 720 C420 750 425 820 425 850 5false183620214M545 750 C437 755 425 820 425 850 5false183620215M425 1055 C425 1025 425 975 425 945 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3620216M530 1010 C471 1013 425 975 425 945 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3620217M180 325 L180 375 L230 325 z10true183620218M425 1245 C425 1275 425 1300 425 1330 5false183620219M550 1240 C495 1256 425 1300 425 1330 5false183620220M425 1515 C425 1485 425 1455 425 1425 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3620221M550 1505 C484 1494 425 1430 425 1400 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3620222M395 1375 L395 1425 L445 1375 z10true183620223M1270 1880 C1270 1850 1270 1812 1270 1782 5false183620224M1650 1885 C1545 1885 1270 1812 1270 1782 5false183620225M1270 1580 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