15191PathwayPhosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:1(9Z))Phosphatidylcholines (PC) are a class of phospholipids that incorporate a phosphocholine headgroup into a diacylglycerol backbone. They are the most abundant phospholipid in eukaryotic cell membranes and has both structural and signalling roles. In eukaryotes, there exist two phosphatidylcholine biosynthesis pathways: the Kennedy pathway and the methylation pathway. The Kennedy pathway begins with the direct phosphorylation of free choline into phosphocholine followed by conversion into CDP-choline and subsequently phosphatidylcholine. It is the major synthesis route in animals. The methylation pathway involves the 3 successive methylations of phosphatidylethanolamine to form phosphatidylcholine. The first reaction of the Kennedy pathway involves the cytosol-localized enzyme choline/ethanolamine kinase catalyzing the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. A parallel Kennedy pathway forms phosphatidylethanolamine from ethanolamine - the only difference being a different enzyme, ethanolamine-phosphate cytidylyltransferase, catalyzing the second step. Phosphatidylethanolamine is also synthesized from phosphatidylserine in the mitochondrial membrane by phosphatidylserine decarboxylase. Phosphatidylethanolamine funnels into the methylation pathway in which phosphatidylethanolamine N-methyltransferase (PEMT) then catalyzes three sequential N-methylation steps to convert phosphatidylethanolamine to phosphatidylcholine. PEMT uses S-adenosyl-L-methionine as a methyl donor.MetabolicPW015383CenterPathwayVisualizationContext1566722623249#000099PathwayVisualization1513815191Phosphatidylcholine Biosynthesis PC(18:3(9Z,12Z,15Z)/18:1(9Z))Phosphatidylcholines (PC) are a class of phospholipids that incorporate a phosphocholine headgroup into a diacylglycerol backbone. They are the most abundant phospholipid in eukaryotic cell membranes and has both structural and signalling roles. In eukaryotes, there exist two phosphatidylcholine biosynthesis pathways: the Kennedy pathway and the methylation pathway. The Kennedy pathway begins with the direct phosphorylation of free choline into phosphocholine followed by conversion into CDP-choline and subsequently phosphatidylcholine. It is the major synthesis route in animals. The methylation pathway involves the 3 successive methylations of phosphatidylethanolamine to form phosphatidylcholine. The first reaction of the Kennedy pathway involves the cytosol-localized enzyme choline/ethanolamine kinase catalyzing the conversion of choline into phosphocholine. Second, choline-phosphate cytidylyltransferase, localized to the endoplasmic reticulum membrane, catalyzes the conversion of phosphocholine to CDP-choline. Last, choline/ethanolaminephosphotransferase catalyzes phosphatidylcholine biosynthesis from CDP-choline. It requires either magnesium or manganese ions as cofactors. A parallel Kennedy pathway forms phosphatidylethanolamine from ethanolamine - the only difference being a different enzyme, ethanolamine-phosphate cytidylyltransferase, catalyzing the second step. Phosphatidylethanolamine is also synthesized from phosphatidylserine in the mitochondrial membrane by phosphatidylserine decarboxylase. Phosphatidylethanolamine funnels into the methylation pathway in which phosphatidylethanolamine N-methyltransferase (PEMT) then catalyzes three sequential N-methylation steps to convert phosphatidylethanolamine to phosphatidylcholine. PEMT uses S-adenosyl-L-methionine as a methyl donor.Metabolic11709019915674Gallego-Ortega D, Ramirez de Molina A, Ramos MA, Valdes-Mora F, Barderas MG, Sarmentero-Estrada J, Lacal JC: Differential role of human choline kinase alpha and beta enzymes in lipid metabolism: implications in cancer onset and treatment. PLoS One. 2009 Nov 12;4(11):e7819. doi: 10.1371/journal.pone.0007819.15191Pathway1709122791820Alatorre-Cobos F, Cruz-Ramirez A, Hayden CA, Perez-Torres CA, Chauvin AL, Ibarra-Laclette E, Alva-Cortes E, Jorgensen RA, Herrera-Estrella L: Translational regulation of Arabidopsis XIPOTL1 is modulated by phosphocholine levels via the phylogenetically conserved upstream open reading frame 30. J Exp Bot. 2012 Sep;63(14):5203-21. doi: 10.1093/jxb/ers180. Epub 2012 Jul 12.15191Pathway1709210893425Henneberry AL, Wistow G, McMaster CR: Cloning, genomic organization, and characterization of a human cholinephosphotransferase. J Biol Chem. 2000 Sep 22;275(38):29808-15. doi: 10.1074/jbc.M005786200.15191Pathway1CellCL:00000005HepatocyteCL:00001822Platelet CL:00002333NeuronCL:00005404Cardiomyocyte CL:00007468Beta cellCL:00006397Epithelial CellCL:00000666MyocyteCL:00001871Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly2Bacteria2ProkaryoteBacteria49Bathymodiolus platifrons220390EukaryoteDeep sea mussel51Picea sitchensis3332EukaryoteSitka spruce19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote60Nitzschia sp.0001EukaryoteNitzschia415NucleusGO:00056345CytoplasmGO:00057371CytosolGO:000582913Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578914Mitochondrial Outer MembraneGO:000574112Mitochondrial Inner MembraneGO:000574325Golgi apparatusGO:00057943Mitochondrial MatrixGO:00057592MitochondrionGO:000573927Peroxisome MembraneGO:000577810Cell MembraneGO:000588631Periplasmic SpaceGO:000562035ChloroplastGO:00095074PeroxisomeGO:000577711Extracellular SpaceGO:000561532Inner MembraneGO:007025819sarcoplasmic reticulumGO:001652924Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032526Golgi apparatus membraneGO:000013939Mitochondrial membraneGO:003196617NucleoplasmGO:00056548Smooth Endoplasmic Reticulum GO:00057901LiverBTO:00007597292Endothelium BTO:00003937Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:0001102741128StomachBTO:0001307155264Adrenal MedullaBTO:00000497189MuscleBTO:000088714118231511PW_BS0000238511PW_BS0000082111PW_BS000002101531PW_BS00010110813PW_BS000108188118PW_BS0000241601181PW_BS0001601951318PW_BS0000242137181PW_BS0000241644PW_BS0001642881441PW_BS000024151141PW_BS0001512491341PW_BS000024221411PW_BS000022181311PW_BS000018171211PW_BS000017315123PW_BS00002412815121PW_BS0001281115121PW_BS0001111321121PW_BS00013213412121PW_BS00013413013121PW_BS00013032914121PW_BS00002817018PW_BS0001703841251PW_BS0001001251351PW_BS0001253821451PW_BS0001002231241PW_BS0000243911261PW_BS0001123951361PW_BS0001133891461PW_BS00011213613171PW_BS00013639914171PW_BS0001134101551PW_BS000115122551PW_BS00012212112171PW_BS000121124151PW_BS00012444415171PW_BS0001151355171PW_BS0001351181171PW_BS00011848515101PW_BS0001152975101PW_BS0000242991101PW_BS000024205561PW_BS000024388161PW_BS000112432511PW_BS00004321425181PW_BS00002435625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS0001154311PW_BS0000043211515PW_BS0000323211PW_BS00000349711PW_BS000049592711PW_BS00005929111PW_BS00002914101PW_BS000014541315PW_BS000054892PW_BS0000891041431PW_BS000104117131PW_BS000117103331PW_BS0001031203171PW_BS0001201333121PW_BS000133107313PW_BS00010716611PW_BS00016619914181PW_BS0000241632181PW_BS0001631985181PW_BS00002421013181PW_BS0000241613181PW_BS000161222341PW_BS0000242253541PW_BS000024226441PW_BS0000242905491PW_BS00002430635511PW_BS0000243183123PW_BS0000243361121PW_BS00002833527121PW_BS0000283317121PW_BS0000281122121PW_BS000112372102PW_BS00002811PW_BS000001406351PW_BS000115407251PW_BS000115429151PW_BS000115383751PW_BS0001004222751PW_BS0001151192171PW_BS0001194641171PW_BS0001153987171PW_BS00011337527171PW_BS0000534793101PW_BS00011548414101PW_BS0001154812101PW_BS00011549127101PW_BS000115501361PW_BS000115206261PW_BS0000245082761PW_BS000115101711PW_BS00001021217181PW_BS0000242851041PW_BS0000243081011PW_BS00002433217121PW_BS00002836210121PW_BS0000283851051PW_BS0001003961061PW_BS00011340010171PW_BS0001131231751PW_BS00012344717171PW_BS00011529817101PW_BS0000245131761PW_BS00011530013101PW_BS00002416212PW_BS00001613121PW_BS0000135411PW_BS000005397113PW_BS0000395811411PW_BS00005827151PW_BS00002746114PW_BS0000466618518PW_BS00006672513PW_BS000072612517PW_BS0000615181PW_BS000051311511PW_BS000031918511PW_BS000091261115PW_BS000026711PW_BS000007971521PW_BS000097100521PW_BS00010012915121PW_BS00012914315191PW_BS0001431465191PW_BS0001461471241PW_BS0001471553241PW_BS0001551783211PW_BS0001782111018PW_BS0000242164181PW_BS0000242171518PW_BS00002421815181PW_BS0000241901118PW_BS0000242771218PW_BS0000242811251PW_BS0000243221231PW_BS000024253541PW_BS0000243331212PW_BS000028350114121PW_BS0000283511512PW_BS00002835325127PW_BS0000281151012PW_BS0001153344121PW_BS0000283683601PW_BS000028184121PW_BS000024943PW_BS000094109323PW_BS000109412125PW_BS00011543311451PW_BS000115408451PW_BS000115405105PW_BS000115435155PW_BS0001154461217PW_BS000115468114171PW_BS0001153744171PW_BS0000533761017PW_BS00005347225177PW_BS0001154701517PW_BS0001154957101PW_BS0001154781010PW_BS0001154991510PW_BS0001155161561PW_BS000115390761PW_BS000112209106PW_BS000024517156PW_BS00011515111PW_BS000015471914PW_BS00004731323PW_BS000024422411PW_BS0000427028511PW_BS000070105113PW_BS0001051572241PW_BS00015715924PW_BS00015915284PW_BS0001521873118PW_BS000024219314PW_BS00002422014PW_BS00002416212181PW_BS000162224241PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000241141112PW_BS00011432711125PW_BS00002834713125PW_BS00002834524121PW_BS000028310312PW_BS00002430412PW_BS000024409115PW_BS0001154241155PW_BS0001154251355PW_BS0001154182451PW_BS0001151371117PW_BS00013745911175PW_BS00011546013175PW_BS00011545424171PW_BS0001154831110PW_BS00011548924101PW_BS00011548012101PW_BS000115208116PW_BS0000245062461PW_BS000115562611PW_BS0000563093911PW_BS000024204111PW_BS00002034141121PW_BS0000284141551PW_BS00011545015171PW_BS0001154824101PW_BS000115502461PW_BS000115301711PW_BS000030509516PW_BS00005033817121PW_BS00002834695126PW_BS00002836139121PW_BS0000283863951PW_BS0001003973961PW_BS00011340139171PW_BS0001134131751PW_BS00011544917171PW_BS000115111811PW_BS00001157Cytidine triphosphateHMDB0000082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C000057CTP427231150827182576610158001087077188759316091371959142213121941641251028815285151153172491534222153741834759174265031577315128784481117873313279949134799571307996432980416170947843849481212594817382986772231106333911132683951132733891155251361155303991203284101208541221213401211222121241229834441234341351247641181256544851258402971263742991272922051279353881202PhosphorylcholineHMDB0001565Phosphorylcholine is a small haptenic molecule, is found in a wide variety of organisms. Human hepatic tumors undergo an elevation in the concentration of phosphorylcholine as the principal metabolic change is observed (PMID: 11076016). Phosphorylcholine is the precursor metabolite of choline in the glycine, serine and threonine metabolism pathways (KEGG, map00260) and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway (KEGG, map00564).107-73-3C00588101418132PHOSPHORYL-CHOLINE989DB03945C[N+](C)(C)CCOP(O)(O)=OC5H15NO4PInChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1YHHSONZFOIEMCP-UHFFFAOYSA-O[2-(trimethylazaniumyl)ethoxy]phosphonic acid184.1507184.073869485-1.702ChoP1-1FDB022692Choline phosphate;N-trimethyl-2-aminoethylphosphonate;O-phosphocholine;Phosphocholine;Phosphoryl-choline;Chop;Phosphorylcholine;Trimethyl(2-(phosphonooxy)ethyl)ammonium;Choline phosphoric acid;N-trimethyl-2-aminoethylphosphonic acidPW_C001202CHOP1511221674349768723921412184151785341327887535694813124113269388115526118122092419124643455125997299126249490127811507170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonooxy)phosphonic acid173.9433173.9119253784pyrophosphoric acid0-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi12235463842923735328822212173162049241059281529417514486854503489525210452941015409117542410354331185458120554811155591325584133560613556551085879107623916669781997073188713416372721607312198731821382751518283210118691611200222212041164123152251232324912512288125792261269529015219306153751834760174256131542697318772353297731712877635336784163357892833179153112799501347995813080047372804171708563019478638494814125948193829867822311063439111327039511327538911552713611553239911993412212001712412003240612033041012093640712126142912134112112148638312240742212298544412350211912383146412404439812497737512532429712539529912541047912559748412565648512587648112655249112686920512693538812695050112733720612812450843034CDP-CholineHMDB0001413Citicoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Once absorbed, citicoline is widely distributed throughout the body, crosses the blood-brain barrier and reaches the central nervous system (CNS), where it is incorporated into the membrane and microsomal phospholipid fraction. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Owing to these pharmacological mechanisms, citicoline has a neuroprotective effect in hypoxic and ischemic conditions, decreasing the volume of ischemic lesion, and also improves learning and memory performance in animal models of brain aging. In addition, citicoline has been shown to restore the activity of mitochondrial ATPase and membrane Na+/K+ATPase, to inhibit activation of certain phospholipases, and to accelerate reabsorption of cerebral edema in various experimental models. Citicoline has also been shown to be able to inhibit mechanisms of apoptosis associated to cerebral ischemia and in certain neurodegeneration models, and to potentiate neuroplasticity mechanisms. Citicoline is a safe drug, as shown by the toxicological tests conducted, that has no significant systemic cholinergic effects and is a well tolerated product (PMID: 17171187).987-78-0C003071158397116436CDP-CHOLINE13207C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=OC14H26N4O11P2InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1RZZPDXZPRHQOCG-OJAKKHQRSA-N{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium488.324488.107330718-1.834[2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium0-1Audes;Cereb;Choline 5'-cytidine diphosphate;Choline cytidine diphosphate;Citicholine;Citicoline;Citidoline;Citifar;Colite;Corenalin;Cyscholin;Cytidine 5'-(choline diphosphate);Cytidine 5'-(cholinyl pyrophosphate);Cytidine 5'-diphosphate choline;Cytidine 5'-diphosphocholine;Cytidine 5-diphosphate-trihydrogen;Cytidine choline diphosphate;Cytidine diphosphate choline;Cytidine diphosphate choline ester;Cytidine diphosphocholine;Cytidine diphosphorylcholine;Cytidine-5' diphosphocholine;Cytidine-5'-pyrophosphate-hydroxycholine;Cytidoline;Difosfocin;Emicholine f;Ensign;Haocolin;Hornbest;Neucolis;Nicholin;Nicolin;Niticolin;P-hydroxide[2-(trimethylammonio)ethyl] ester;Reagin;Recofnan;Recognan;Rexort;Sintoclar;Somazina;Somazine;Suncholin;[2-cytidylate-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium;Cdp-colina;Citicolina;Citicolinum;Citidin difosfato de colina;Cyticholine;Cytidindiphosphocholin;Cytidine 5'-diphosphoric choline;[2-cytidylic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium;Cytidine 5'-(choline diphosphoric acid);Cytidine 5'-(cholinyl pyrophosphoric acid)PW_C043034CDP-C12195164152861511533527995913294815124113271388115528118149O-PhosphoethanolamineHMDB0000224Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524, 8588821, 11566853).1071-23-4C00346101517553PHOSPHORYL-ETHANOLAMINE990NCCOP(O)(O)=OC2H8NO4PInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)SUHOOTKUPISOBE-UHFFFAOYSA-N(2-aminoethoxy)phosphonic acid141.063141.019094261-0.743phosphorylethanolamine0-1FDB0219112-amino-ethanol dihydrogen phosphate;2-amino-ethanol dihydrogen phosphate (ester);2-amino-ethanol phosphate;2-aminoethanol o-phosphate;2-aminoethyl dihydrogen phosphate;2-aminoethyl dihydrogen phosphate (acd/name 4.0);2-aminoethyl phosphate;Colamine acid phosphate;Colamine phosphate;Colamine phosphoric acid;Colaminephosphoric acid;Colaminphosphoric acid;Eap;Ethanolamine o-phosphate;Ethanolamine acid phosphate;Ethanolamine phosphate;Mono(2-aminoethyl) phosphate;Monoaminoethyl phosphate;O-phosphocolamine;O-phosphoethanolamine;O-phosphorylethanolamine;Ope;Petn;Phosphoethanolamine;Phosphonoethanolamine;Phosphoric acid 2-aminoethyl phenyl ester;Phosphoryethanolamine;Phosphorylethanolamine;Pe;Pea;Phosphoryl-ethanolamine;2-amino-ethanol dihydrogen phosphoric acid;2-aminoethyl dihydrogen phosphoric acid;2-amino-ethanol phosphoric acid;Colaminphosphate;Ethanolamine acid phosphoric acid;Ethanolamine o-phosphoric acid;Ethanolamine phosphoric acid;Mono(2-aminoethyl) phosphoric acid;Monoaminoethyl phosphoric acid;Phosphate 2-aminoethyl phenyl ester;Ethamp;O-phosphonatoethanaminiumPW_C000149Ethamp21181049788721421212179285153283081535515115376278853332799653627997713294818385948551241132743961155314001157471181220671231246184471262222981277845131201CDP-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-Etala3384181529028815343224089549785711307996632979978331948203829485638311327638911553339911574939812260312512517513612675030012834439596EthanolamineHMDB0000149Ethanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.141-43-5C0018970016000ETHANOL-AMINE13835336DB03994NCCOC2H7NOInChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2HZAXFHJVJLSVMW-UHFFFAOYSA-N2-aminoethan-1-ol61.083161.0527638511.142ethanolamine01FDB0007691-amino-2-hydroxyethane;2-amino-1-ethanol;2-aminoethanol;2-aminoethyl alcohol;2-ethanolamine;2-hydroxyethanamine;2-hydroxyethylamine;Aethanolamin;Aminoethanol;Colamine;Envision conditioner pdd 9020;Ethanolamine;Ethylolamine;Glycinol;H-glycinol;Mea;Monoaethanolamin;Monoethanolamine;Olamine;B-aminoethanol;B-aminoethyl alcohol;B-ethanolamine;B-hydroxyethylamine;Beta-aminoethanol;Beta-aminoethyl alcohol;Beta-ethanolamine;Beta-hydroxyethylamine;Eta;2-amino-ethanol;2-aminoethan-1-ol;Hea;β-aminoethanol;β-aminoethyl alcohol;β-ethanolamine;β-hydroxyethylaminePW_C000096ETA15648914624912174151153262785421117997113294825124113281388115538118121333122123903135126013297127465205414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP23413484152248213801596315978310611415182190149210418211310216158240859243527272847273646285529316572363561440023447631477091503626515775208975217100531511153491125392103544612055441295572133562410857411175764101584914358561465878107589914759261516050155611116162311666495178670094684118868721607159205718720672082107226213723121173001987303216739121774102187433163748322281872251185127711905170120132811218028513262223153293084232831542398313426223224269631877029253770871327721613477306329774723337766333678039332780433507817012878215351782443537841433578495115787053317884913078920334800303688062211880651135806761199482712411328338811620410911994412211999440612015640712031838212036641212124842912139412312139943312147240812189938312197641012206412512208540512240542212244543512297339912301344612381846412395344712395846812403037412445239812452944412461513612463637612494747212497537512501247012533429712537347912549229912551748112564548412612548512621930012623549512624247812655049112659749912691550112773351612778039512779739012780320912812250812816851712831338940034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039565CholineHMDB0000097Choline 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.62-49-7C0011430515354CPD-563299DB00122C[N+](C)(C)CCOC5H14NOInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1OEYIOHPDSNJKLS-UHFFFAOYSA-N(2-hydroxyethyl)trimethylazanium104.1708104.107539075-1.591choline11FDB000710(2-hydroxyethyl)trimethyl ammonium;(2-hydroxyethyl)trimethylammonium;(beta-hydroxyethyl)trimethylammonium;2-hydroxy-n,n,n-trimethyl-ethanaminium;2-hydroxy-n,n,n-trimethylethanaminium;Bilineurine;Biocolina;Biocoline;Choline;Choline cation;Choline ion;Cholinum;Hepacholine;Hormocline;Lipotril;N,n,n-trimethylethanol-ammonium;N,n,n-trimethylethanolammonium;Neocolina;Paresan;N-trimethylethanolamine;TrimethylethanolaminePW_C000065Choline562356415565814971456121195619137684971218515112197164122782261533921538049776141127761911478530115799721327998033194829124948593831132853881155411181157533981204894071204974091213064051238763761259874781264714811274402091280402063356DG(18:3(9Z,12Z,15Z)/18:1(9Z)/0:0)HMDB0007305DG(18:3(9Z,12Z,15Z)/18:1(9Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:3(9Z,12Z,15Z)/18:1(9Z)/0:0), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.C001655347814775578DIACYLGLYCEROL24766055[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCCCCC39H68O5InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,37,40H,3-4,6,8-10,12,14-16,21-36H2,1-2H3/b7-5-,13-11-,19-17-,20-18-/t37-/m0/s1LYYSCXLWEIVEFO-LGRGBMOQSA-N(2S)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propyl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate616.9542616.506675286-7.531diacylglycerol00FDB0244981-a-linolenoyl-2-oleoyl-sn-glycerol;1-alpha-linolenoyl-2-oleoyl-sn-glycerol;Dag(18:3/18:1);Dag(18:3n3/18:1n9);Dag(18:3w3/18:1w9);Dag(36:4);Dg(18:3/18:1);Dg(18:3n3/18:1n9);Dg(18:3w3/18:1w9);Dg(36:4);Diacylglycerol;Diacylglycerol(18:3/18:1);Diacylglycerol(18:3n3/18:1n9);Diacylglycerol(18:3w3/18:1w9);Diacylglycerol(36:4);Diglyceride;1-(9z,12z,15z)-octadecatrienoyl-2-(9z)-octadecenoyl-sn-glycerol;Dg (18:3(n-3)/18:1(n-9)/0:0);Sn-1-alpha-linolenoyl-2-oleoyl diglyceridePW_C003356DG36:413226151177534964Cytidine 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_C000064CMP11518251214273423386184972565768101580210870791887595160914724991512249257195121961641221015115274285153363081537349348151742652315784491117848811578573130787361327995313479969331804211709479138494821383986802231106373911132773901155353981208551221213461211222161241224874051226051251234351351247681181250533761251771361258412971263782991266414781267523001272932051279403881282172091283463955206PE(18:3(9Z,12Z,15Z)/18:1(9Z))HMDB0009158PE(18:3(9Z,12Z,15Z)/18:1(9Z)) 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(18:3(9Z,12Z,15Z)/18:1(9Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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.C0035052924891L-1-PHOSPHATIDYL-ETHANOLAMINE24768620[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN)OC(=O)CCCCCCC\C=C/CCCCCCCCC41H74NO8PInChI=1S/C41H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(43)47-37-39(38-49-51(45,46)48-36-35-42)50-41(44)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,39H,3-4,6,8-10,12,14-16,21-38,42H2,1-2H3,(H,45,46)/b7-5-,13-11-,19-17-,20-18-/t39-/m1/s1QLXOJXUXNJLYFV-REUDLEIBSA-N(2-aminoethoxy)[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphinic acid740.0019739.515204861-6.9922-aminoethoxy(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphinic acid00C003501-a-linolenoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine;1-alpha-linolenoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine;Gpetn(18:3/18:1);Gpetn(18:3n3/18:1n9);Gpetn(18:3w3/18:1w9);Gpetn(36:4);Pe(18:3/18:1);Pe(18:3n3/18:1n9);Pe(18:3w3/18:1w9);Pe(36:4);Phophatidylethanolamine(18:3/18:1);Phophatidylethanolamine(18:3n3/18:1n9);Phophatidylethanolamine(18:3w3/18:1w9);Phophatidylethanolamine(36:4)PW_C005206PE36:417754491775530923290177939PS(18:3(9Z,12Z,15Z)/18:1(9Z))HMDB0012412PS(18:3(9Z,12Z,15Z)/18:1(9Z)) is a phosphatidylserine (PS or GPSer). It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoserines 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. PS(18:3(9Z,12Z,15Z)/18:1(9Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. It is usually less than 10% of the total phospholipids, the greatest concentration being in myelin from brain tissue. However, it may comprise 10 to 20 mol% of the total phospholipid in the plasma membrane and endoplasmic reticulum of the cell. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine, especially during bone formation for example. As phosphatidylserine is located entirely on the inner monolayer surface of the plasma membrane (and of other cellular membranes) and it is the most abundant anionic phospholipids. Therefore phosphatidylseriine may make the largest contribution to interfacial effects in membranes involving non-specific electrostatic interactions. This normal distribution is disturbed during platelet activation and cellular apoptosis. In human plasma, 1-stearoyl-2-oleoyl and 1-stearoyl-2-arachidonoyl species predominate, but in brain (especially grey matter), retina and many other tissues 1-stearoyl-2-docosahexaenoyl species are very abundant. Indeed, the ratio of n-3 to n-6 fatty acids in brain phosphatidylserine is very much higher than in most other lipids. 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. Phosphatidylserines typically carry a net charge of -1 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. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.C027375292598318303L-1-PHOSPHATIDYL-SERINE13628254DB00144[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)OC(=O)CCCCCCC\C=C/CCCCCCCC)C(O)=OC42H74NO10PInChI=1S/C42H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-40(44)50-35-38(36-51-54(48,49)52-37-39(43)42(46)47)53-41(45)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h5,7,11,13,17-20,38-39H,3-4,6,8-10,12,14-16,21-37,43H2,1-2H3,(H,46,47)(H,48,49)/b7-5-,13-11-,19-17-,20-18-/t38-,39+/m1/s1FCMMQVCGAUYOQK-SRXFDEGJSA-N(2S)-2-amino-3-({hydroxy[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy]phosphoryl}oxy)propanoic acid784.0114783.505034105-6.983(2S)-2-amino-3-{[hydroxy(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxyphosphoryl]oxy}propanoic acid0-11-a-linolenoyl-2-oleoyl-sn-glycero-3-phosphoserine;1-alpha-linolenoyl-2-oleoyl-sn-glycero-3-phosphoserine;Ps(18:3/18:1);Ps(18:3n3/18:1n9);Ps(18:3w3/18:1w9);Ps(36:4);Pser(18:3/18:1);Pser(18:3n3/18:1n9);Pser(18:3w3/18:1w9);Pser(36:4);Phosphatidylserine(18:3/18:1);Phosphatidylserine(18:3n3/18:1n9);Phosphatidylserine(18:3w3/18:1w9);Phosphatidylserine(36:4)PW_C007939PS36:417758309232884923289171316Carbon dioxideHMDB0001967Carbon dioxide is a colorless, odorless gas that can be formed by the body and is necessary for the respiration cycle of plants and animals. Carbon dioxide is produced during respiration by all animals, fungi and microorganisms that depend on living and decaying plants for food, either directly or indirectly. It is, therefore, a major component of the carbon cycle. Additionally, carbon dioxide is used by plants during photosynthesis to make sugars which may either be consumed again in respiration or used as the raw material to produce polysaccharides such as starch and cellulose, proteins and the wide variety of other organic compounds required for plant growth and development. When inhaled at concentrations much higher than usual atmospheric levels, it can produce a sour taste in the mouth and a stinging sensation in the nose and throat. These effects result from the gas dissolving in the mucous membranes and saliva, forming a weak solution of carbonic acid. Carbon dioxide is used by the food industry, the oil industry, and the chemical industry. Carbon dioxide is used to produce carbonated soft drinks and soda water. Traditionally, the carbonation in beer and sparkling wine comes about through natural fermentation, but some manufacturers carbonate these drinks artificially.124-38-9C0001128016526274O=C=OCO2InChI=1S/CO2/c2-1-3CURLTUGMZLYLDI-UHFFFAOYSA-Nmethanedione44.009543.9898292440.630carbon dioxide00DBMET00423FDB014084Carbon oxide;Carbon-12 dioxide;Carbonic acid anhydride;Carbonic acid gas;Carbonic anhydride;[co2];Co2;E 290;E-290;E290;R-744PW_C001316CO25081211204448013503186403677316952080651133431638491745225511731447052831035320111575010857711015968100602615560781616471178663710769221907017160703516370611887163205730819873332137461222753021082152258223151915824911849277119081701246422612688290426263154352331876994293771221337717013277470333777391127775012977763341780771347840535678427334789413317922713080008368806751198071713594836384113291391115549121119954406120089122120155407120364412120556414120833419120922124120991408121284125121505383122744120123011446123190450123418455123489118123556374123855136124063398125344479125460297125516481125824490125870299125931482126280480126887501127052206127277507127331388127390502921S-AdenosylmethionineHMDB0001185S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.485-80-3C000192476216515414S-ADENOSYLMETHIONINE31983DB00118C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NC15H23N6O5SInChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1MEFKEPWMEQBLKI-AIRLBKTGSA-O[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium399.445399.145063566-2.565SAMe11FDB022473(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;SamePW_C000921SAMe519863330704201220318802720662468110502350560413571361637540210754421376321608266151923519511874198120312221235822515293249153451815363309768972937689916476984224774881117773133877772341780991327830335178335346791551127996136180861229483038294833386113286389113288397115543399115546401120393122120537413120939407121052124122282435123171449123505119123616118124836470125859297125879481126304299126447499127321205127340206127595388128017517749S-AdenosylhomocysteineHMDB0000939S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).979-92-0C000212524622216680ADENOSYL-HOMO-CYS388301N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=OC14H20N6O5SInChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1ZJUKTBDSGOFHSH-WFMPWKQPSA-N(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid384.411384.12158847-1.975S-adenosyl-L-homocysteine00DBMET00514FDB022327(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteinePW_C000749SAH520857518635307052012213188227206724683105025505607136713716375422107546213763416082681519237195118751981235922515294249153643097748911177611130777333387777334178098132783053517833734679156112799623618086322948313829483438611328738911328939711554439911554740112039412212048612512053941312094040712105312412228443512303713512317344912350611912361711812483847012588048112630329912644949912734120612759638812801951759352PE-NMe(18:3(9Z,12Z,15Z)/18:1(9Z))HMDB0113228PE-NMe(18:3(9Z,12Z,15Z)/18:1(9Z)) is a monomethylphosphatidylethanolamine. It is a glycerophospholipid, and it is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Monomethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PE-NMe(18:3(9Z,12Z,15Z)/18:1(9Z)), in particular, consists of one chain of alpha-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids are ubiquitous in nature. They are key components of the cell lipid bilayer and are involved in metabolism and signaling.C01241 15958CPD-405[H]C(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCC\C=C/CCCCCCCCC42H76NO8PInChI=1S/C42H76NO8P/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43-3)51-42(45)35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-5-2/h6,8,12,14,18-21,40,43H,4-5,7,9-11,13,15-17,22-39H2,1-3H3,(H,46,47)/b8-6-,14-12-,20-18-,21-19-KRJGZACFGKKDAA-RSCSKNAVSA-N[2-(methylamino)ethoxy]({2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy})phosphinic acid754.043753.530855409-7.1822-(methylamino)ethoxy(2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy)phosphinic acid001-alpha-linolenoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine-N-monomethyl;PE-NMe(18:3/18:1);PE-NMe(18:3n3/18:1n9);PE-NMe(18:3w3/18:1w9);PE-NMe(36:4);MMPE(18:3(9Z,12Z,15Z)/18:1(9Z));MMPE(18:3/18:1);MMPE(18:3n3/18:1n9);MMPE(18:3w3/18:1w9);MMPE(36:4);monomethylphosphatidylethanolamine;N-monomethylphosphatidylethanolamine;phosphatidyl-N-methylethanolaminePW_C059352MMPE(361775930960147PE-NMe2(18:3(9Z,12Z,15Z)/18:1(9Z))HMDB0114130PE-NMe2(18:3(9Z,12Z,15Z)/18:1(9Z)) is a dimethylphosphatidylethanolamine. It is a glycerophospholipid, and it is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Dimethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PE-NMe2(18:3(9Z,12Z,15Z)/18:1(9Z)), in particular, consists of one chain of alpha-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids are ubiquitous in nature. They are key components of the cell lipid bilayer and are involved in metabolism and signaling.C0430852332CPD-160[H]C(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)(COP(O)(=O)OCCN(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCCC43H78NO8PInChI=1S/C43H78NO8P/c1-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-42(45)49-39-41(40-51-53(47,48)50-38-37-44(3)4)52-43(46)36-34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-2/h7,9,13,15,19-22,41H,5-6,8,10-12,14,16-18,23-40H2,1-4H3,(H,47,48)/b9-7-,15-13-,21-19-,22-20-HSGYUKMNAHIAOS-KVXNSCJWSA-N[2-(dimethylamino)ethoxy]({2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy})phosphinic acid768.07767.546505474-7.1912-(dimethylamino)ethoxy(2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propoxy)phosphinic acid001-alpha-linolenoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethylethanolamine;PE-NMe2(18:3/18:1);PE-NMe2(18:3n3/18:1n9);PE-NMe2(18:3w3/18:1w9);PE-NMe2(36:4);DMPE(18:3(9Z,12Z,15Z)/18:1(9Z));DMPE(18:3/18:1);DMPE(18:3n3/18:1n9);DMPE(18:3w3/18:1w9);DMPE(36:4);dimethylphosphatidylethanolamine;N-dimethylphosphatidylethanolamine;phosphatidyl-N-dimethylethanolamine;phosphatidyl-N,N-dimethylethanolaminePW_C060147DMPE(36177603094251PC(18:3(9Z,12Z,15Z)/18:1(9Z))HMDB0008203PC(18:3(9Z,12Z,15Z)/18:1(9Z)) 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(18:3(9Z,12Z,15Z)/18:1(9Z)), in particular, consists of one chain of a-linolenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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. 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.C0015724778989 PHOSPHATIDYLCHOLINE24766865CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC)COP([O-])(=O)OCC[N+](C)(C)CC44H80NO8PInChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h8,10,14,16,20-23,42H,6-7,9,11-13,15,17-19,24-41H2,1-5H3/b10-8-,16-14-,22-20-,23-21-/t42-/m1/s1LPDGUCIMNBNWEJ-BXZVQSHESA-Ntrimethyl(2-{[(2R)-2-[(9Z)-octadec-9-enoyloxy]-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyloxy]propyl phosphonato]oxy}ethyl)azanium782.0817781.562155053-7.420lecithin00FDB0253931-a-linolenoyl-2-oleoyl-sn-glycero-3-phosphocholine;1-alpha-linolenoyl-2-oleoyl-sn-glycero-3-phosphocholine;Gpcho(18:3/18:1);Gpcho(18:3n3/18:1n9);Gpcho(18:3w3/18:1w9);Gpcho(36:4);Lecithin;Pc aa c36:4;Pc(18:3/18:1);Pc(18:3n3/18:1n9);Pc(18:3w3/18:1w9);Pc(36:4);Phosphatidylcholine(18:3/18:1);Phosphatidylcholine(18:3n3/18:1n9);Phosphatidylcholine(18:3w3/18:1w9);Phosphatidylcholine(36:4);Phosphatidylcholine (1-18:3-2-18:1);18:3-18:1-pcPW_C004251Lecithi177564917757309232871811847Choline-phosphate cytidylyltransferase AP49585Controls phosphatidylcholine synthesis.HMDBP00755PCYT1A3q29CH47119112.7.7.1515358181536749246872246888697Ethanolamine-phosphate cytidylyltransferaseQ99447Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
HMDBP00738PCYT217q25.3CH47109912.7.7.1441298153704911846Choline kinase alphaP35790Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.HMDBP00778CHKA11q13.2BC03647112.7.1.32;2.7.1.8215351211849Choline/ethanolaminephosphotransferase 1Q9Y6K0Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.HMDBP03349CEPT11p13.3AF13886212.7.8.1;2.7.8.2153724925475181860Phosphatidylserine decarboxylase proenzymeQ9UG56HMDBP02255PISD22q12.2BC00931514.1.1.65156910153711778Phosphatidylethanolamine N-methyltransferaseQ9UBM1Catalyzes three sequential methylation reactions of phosphatidylethanolamine (PE) by AdoMet, thereby producing phosphatidylcholine (PC).
HMDBP00081PEMT17p11.2AF29446612.1.1.17; 2.1.1.7157618155711466621536530980862225656Choline-phosphate cytidylyltransferase1PW_P00565613126118471535418970Ethanolamine-phosphate cytidylyltransferase1PW_P000970109669715654Choline/ethanolamine kinase1PW_P00565413124118461535225657Choline/ethanolaminephosphotransferase1PW_P005657131271184915356185662Phosphatidylserine decarboxylase1PW_P005662131321860153573172Phosphatidylethanolamine N-methyltransferase1PW_P00017219078149894PW_R049894Right158486571Compoundtrue15848712021Compoundfalse1584881701Compoundtrue158489430341Compoundfalse4001956562.7.7.1549900PW_R049900Right158512571Compoundtrue1585131491Compoundfalse1585141701Compoundtrue15851512011Compoundfalse400259702.7.7.1449890PW_R049890Right158466961Compoundfalse1584674141Compoundtrue1584681491Compoundfalse15846910341Compoundtrue158470400341Compoundtrue4001556542.7.1.8249897PW_R049897Right158499651Compoundfalse1585004141Compoundtrue15850112021Compoundfalse15850210341Compoundtrue40022565451692PW_R051692Right16568412011Compoundfalse16568533561Compoundfalse165686641Compoundfalse16568752061Compoundfalse41817565751694PW_R051694Right16569379391Compoundfalse16569452061Compoundfalse16569513161Compoundfalse41819566251695PW_R051695Right1656969211Compoundfalse16569752061Compoundfalse1656987491Compoundfalse165699593521Compoundfalse4182017251696PW_R051696Right165700593521Compoundfalse1657019211Compoundfalse165702601471Compoundfalse1657037491Compoundfalse418211722.1.1.7151697PW_R051697Right1657049211Compoundfalse165705601471Compoundfalse1657067491Compoundfalse16570742511Compoundfalse418221722.1.1.7151693PW_R051693Right165688430341Compoundfalse16568933561Compoundfalse165690641Compoundfalse165691400341Compoundfalse16569242511Compoundfalse41818565772888957183false253054110regular10011072889057223false59554810regular100110728891120223false240040610regular1001007288921701845false252784410regular63437288931702245false63782610regular63437288944303423false240088610regular1001007288951493083false72540310regular1001107288961201223false72588310regular1001107288979623false27340910regular100100728898414242false37332910regular5030728899414242false280234010regular50307289001034243false67333010regular50307289011034243false250234010regular5030728902400344955false2671121210regular787872890340034255false66421510regular78787289046523false285240510regular1001007289113356493false86594310regular1001007289123356493false225595110regular10010072891364493false600121810regular10011072891464493false2521121610regular1001107289155206493false800126310regular1001007289165206173false799175210regular10010072891752063093false799158010regular1001007289227939173false349175110regular10010072892313161752false750190710regular78787289249213093false1380141810regular1001107289259213093false1875142310regular1001107289269213093false899142010regular1001107289277493093false1730142310regular1001107289287493093false2225141810regular1001107289297493093false1245141810regular100110728932593523093false1320157310regular100110728935601473093false1800157310regular10011072894442513093false2325157810regular1001007289454251493false2326126110regular1001003382331184749119false22957038proteinregular1608033823469749119false7677078proteinregular160803382351184626false4634178proteinregular160803382361184626false25974178proteinregular16080338238118494999false77510988proteinregular1507033824018601799false54917688proteinregular150703382417830999false105215958subunitregular150703382437830999false152715958subunitregular150703382477830999false202515958proteinregular15070338248118494999false230010968proteinregular15070230453565615138183374073382332304549701513849337408338234230455565415138233740933823523045656541513823374103382362304585657151384933741233823823046056621513817337414338240230461172151383093374153382412304631721513830933741733824323046717215138309337421338247230468565715138493374223382481049144M849 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84false62203.01.07626415Endoplasmic Reticulum Membrane15161300201.01.0160157626515Mitochondrial Outer Membrane3061582201.01.0160157626615Cytosol254199201.01.0160157626715Endoplasmic Reticulum Lumen15141245201.01.0160157626815Mitochondrial Intermembrane Spance3041647201.01.0160157626915Mitochondrial Matrix23091823201.01.0160157627015Mitochondrial Inner Membrane23091753201.01.0160151851011588438851593237113704#FFEEDE415207771851022666167629515962499201640#FFEBEB42204420