2267PathwayGlycerophospholipid MetabolismThe metabolism of glycerophospholipid begins with glycerone phosphate either reacting with glycerol-3-phosphate dehydrogenase resulting in the release of glycerol-3-phosphate or it can react with glycerol-3-phosphate O-acyltransferase / dihydroxyacetone phosphate acyltransferase resulting in the release of a 1-acylglycerone 3-phosphate.
Glycerol-3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of an acyl glycerol phosphate. 1-acylglycerone 3-phosphate 1-acyl dihydroxyacetone phosphate reductase resulting in the release of a acyl glycerol phosphate. The latter compound then reacts with a oleoyl-CoA: lysophosphatidate acyltransferase resulting in the release of a phosphatidic acid. The latter compound reacts with Phosphatidic acid phosphohydrolase 1 resulting in the release of diacyl glycerol. This compound can be metabolized through a CTP-dependent diacylglycerol kinase 1 resulting in the release of a phosphatidic acid. Diacyl glycerol reacts with cdp-ethanolamine through a bifunctional diacylglycerol cholinephosphotransferase/ethanolaminephosphotransferase resulting in the release of a phosphatidyl ethanolamine.
MetabolicPW002493CenterPathwayVisualizationContext277931003303#000099PathwayVisualization22502267Glycerophospholipid MetabolismThe metabolism of glycerophospholipid begins with glycerone phosphate either reacting with glycerol-3-phosphate dehydrogenase resulting in the release of glycerol-3-phosphate or it can react with glycerol-3-phosphate O-acyltransferase / dihydroxyacetone phosphate acyltransferase resulting in the release of a 1-acylglycerone 3-phosphate.
Glycerol-3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of an acyl glycerol phosphate. 1-acylglycerone 3-phosphate 1-acyl dihydroxyacetone phosphate reductase resulting in the release of a acyl glycerol phosphate. The latter compound then reacts with a oleoyl-CoA: lysophosphatidate acyltransferase resulting in the release of a phosphatidic acid. The latter compound reacts with Phosphatidic acid phosphohydrolase 1 resulting in the release of diacyl glycerol. This compound can be metabolized through a CTP-dependent diacylglycerol kinase 1 resulting in the release of a phosphatidic acid. Diacyl glycerol reacts with cdp-ethanolamine through a bifunctional diacylglycerol cholinephosphotransferase/ethanolaminephosphotransferase resulting in the release of a phosphatidyl ethanolamine.
Metabolic18529217675291Benghezal M, Roubaty C, Veepuri V, Knudsen J, Conzelmann A: SLC1 and SLC4 encode partially redundant acyl-coenzyme A 1-acylglycerol-3-phosphate O-acyltransferases of budding yeast. J Biol Chem. 2007 Oct 19;282(42):30845-55. doi: 10.1074/jbc.M702719200. Epub 2007 Aug 3.2267Pathway529316916618Czabany T, Athenstaedt K, Daum G: Synthesis, storage and degradation of neutral lipids in yeast. Biochim Biophys Acta. 2007 Mar;1771(3):299-309. doi: 10.1016/j.bbalip.2006.07.001. Epub 2006 Jul 13.2267Pathway52948408076Nagiec MM, Wells GB, Lester RL, Dickson RC: A suppressor gene that enables Saccharomyces cerevisiae to grow without making sphingolipids encodes a protein that resembles an Escherichia coli fatty acyltransferase. J Biol Chem. 1993 Oct 15;268(29):22156-63.2267Pathway529511544256Zheng Z, Zou J: The initial step of the glycerolipid pathway: identification of glycerol 3-phosphate/dihydroxyacetone phosphate dual substrate acyltransferases in Saccharomyces cerevisiae. J Biol Chem. 2001 Nov 9;276(45):41710-6. doi: 10.1074/jbc.M104749200. Epub 2001 Sep 5.2267Pathway529616807089Carman GM, Han GS: Regulation of phospholipid synthesis in Saccharomyces cerevisiae by zinc depletion. Biochim Biophys Acta. 2007 Mar;1771(3):322-30. doi: 10.1016/j.bbalip.2006.05.006. Epub 2006 May 19.2267Pathway52978982874Min-Seok R, Kawamata Y, Nakamura H, Ohta A, Takagi M: Isolation and characterization of ECT1 gene encoding CTP: phosphoethanolamine cytidylyltransferase of Saccharomyces cerevisiae. J Biochem. 1996 Nov;120(5):1040-7.2267Pathway1CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000662Platelet CL:00002338Beta cellCL:00006394Arabidopsis thaliana3702EukaryoteThale cress1Homo sapiens9606EukaryoteHuman2Bacteria2ProkaryoteBacteria3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia425Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast51Picea sitchensis3332EukaryoteSitka spruce12Mitochondrial Inner MembraneGO:00057433Mitochondrial MatrixGO:00057592MitochondrionGO:00057395CytoplasmGO:00057377Endoplasmic Reticulum MembraneGO:00057891CytosolGO:00058294PeroxisomeGO:00057776LysosomeGO:000576413Endoplasmic ReticulumGO:000578316Lysosomal LumenGO:004320235ChloroplastGO:000950711Extracellular SpaceGO:000561514Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562010Cell MembraneGO:000588636MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025825Golgi apparatusGO:000579427Peroxisome MembraneGO:00057788Smooth Endoplasmic Reticulum GO:000579019sarcoplasmic reticulumGO:001652918Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563440PeriplasmGO:004259726Golgi apparatus membraneGO:000013939Mitochondrial membraneGO:00319661LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274115cardiocyteBTO:00015394Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273102Endothelium BTO:000039318PancreasBTO:00009882231241PW_BS000024222341PW_BS0000244311PW_BS0000043211PW_BS0000038511PW_BS000008101711PW_BS0000102111PW_BS0000025411PW_BS000005541315PW_BS00005449711PW_BS000049171211PW_BS00001729111PW_BS0000299611PW_BS000009181311PW_BS0000182811611PW_BS0000286131PW_BS000006311511PW_BS000031951721PW_BS000095103331PW_BS0001031115121PW_BS0001111122121PW_BS0001121231751PW_BS0001231251351PW_BS0001251355171PW_BS000135100521PW_BS00010010813PW_BS00010814117191PW_BS0001411471241PW_BS000147151141PW_BS0001511553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS000178117131PW_BS0001171601181PW_BS000160188118PW_BS0000241632181PW_BS000163205561PW_BS000024206261PW_BS000024226441PW_BS0000242253541PW_BS000024224241PW_BS0000241985181PW_BS0000242164181PW_BS0000242491341PW_BS00002429817101PW_BS00002430013101PW_BS0000243221231PW_BS000024315123PW_BS0000241321121PW_BS0001321333121PW_BS00013313412121PW_BS0001343317121PW_BS0000283361121PW_BS0000283344121PW_BS00002833217121PW_BS00002813013121PW_BS0001301136121PW_BS00011334713125PW_BS0000283683601PW_BS0000281192171PW_BS000119124151PW_BS000124388161PW_BS000112943PW_BS0000941181171PW_BS000118406351PW_BS000115407251PW_BS000115122551PW_BS000122408451PW_BS0001154251355PW_BS000115126651PW_BS000126429151PW_BS000115383751PW_BS0001003841251PW_BS0001001203171PW_BS00012044717171PW_BS00011513613171PW_BS0001363744171PW_BS00005346013175PW_BS0001154436171PW_BS0001154641171PW_BS0001153987171PW_BS00011312112171PW_BS0001214793101PW_BS0001154812101PW_BS0001152975101PW_BS0000242991101PW_BS0000244824101PW_BS0001154957101PW_BS00011548012101PW_BS000115501361PW_BS000115502461PW_BS000115390761PW_BS0001123911261PW_BS0001123951361PW_BS00011315111PW_BS000015261115PW_BS000026221411PW_BS000022422411PW_BS0000427028511PW_BS000070107313PW_BS000107105113PW_BS0001051572241PW_BS00015715924PW_BS00015916611PW_BS00016615284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS0000242137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS00017016212181PW_BS0001621951318PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000241141112PW_BS00011432711125PW_BS00002834524121PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109409115PW_BS0001154241155PW_BS0001154182451PW_BS0001151371117PW_BS00013745911175PW_BS00011545424171PW_BS0001154831110PW_BS00011548924101PW_BS000115208116PW_BS0000245062461PW_BS000115432511PW_BS00004335625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS0001155811411PW_BS000058350114121PW_BS000028253541PW_BS00002443311451PW_BS000115468114171PW_BS00011514101PW_BS0000141021231PW_BS0001021041431PW_BS00010419914181PW_BS00002432914121PW_BS0000281151012PW_BS0001153331212PW_BS0000283821451PW_BS0001002881441PW_BS0000243891461PW_BS000112405105PW_BS00011539914171PW_BS0001133761017PW_BS00005348414101PW_BS0001154781010PW_BS000115209106PW_BS000024592711PW_BS000059111811PW_BS00001112915121PW_BS00012933527121PW_BS0000284141551PW_BS0001154222751PW_BS00011545015171PW_BS00011537527171PW_BS00005349127101PW_BS0001155082761PW_BS0001153551914PW_BS0000352111018PW_BS00002413121PW_BS000013204111PW_BS000020331811PW_BS0000332441011PW_BS00002460251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS00011012711651PW_BS000127140103PW_BS00014014315191PW_BS0001431465191PW_BS0001461802211PW_BS000180207661PW_BS00002421425181PW_BS0000242156181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS0000283522512PW_BS00002835325127PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154151851PW_BS00011543441051PW_BS000115436255PW_BS0001154461217PW_BS000115448116171PW_BS00011545118171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS0001155041861PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS000047231511PW_BS000023241529PW_BS00002425715291PW_BS00002412815121PW_BS0001284101551PW_BS00011544415171PW_BS00011548515101PW_BS0001151971418PW_BS0000241893218PW_BS000024562611PW_BS0000563093911PW_BS000024231391PW_BS00002436139121PW_BS0000283863951PW_BS00010040139171PW_BS00011336210121PW_BS0000283851051PW_BS0001003961061PW_BS00011340010171PW_BS0001133211515PW_BS000032892PW_BS00008930635511PW_BS000024372102PW_BS00002816212PW_BS000016397113PW_BS0000396618518PW_BS0000665181PW_BS000051918511PW_BS0000912171518PW_BS00002421815181PW_BS0000243511512PW_BS000028184121PW_BS000024435155PW_BS0001154701517PW_BS0001154991510PW_BS0001155161561PW_BS000115517156PW_BS00011531323PW_BS00002442631Glycerone phosphateDihydroxyacetone phosphate dilithium salt 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 dilithium salt is soluble (in water) and a moderately acidic compound (based on its pKa).[Li+].[Li+].OCC(=O)COP([O-])([O-])=OC3H5Li2O6PInChI=1S/C3H7O6P.2Li/c4-1-3(5)2-9-10(6,7)8;;/h4H,1-2H2,(H2,6,7,8);;/q;2*+1/p-2QWIKESRFRWLYIA-UHFFFAOYSA-Ldilithium(1+) ion 1-hydroxy-3-(phosphonatooxy)propan-2-one181.924182.014382502-0.701dilithium(1+) ion dihydroxyacetone phosphate0-2PW_C042631GlyPhop12547223129142221144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH1434153349086481011152127551469542230492781172836293109948061848121848212849046495931516995524010353321115358112546612354791255593135569810057371085829141591514759451516027155607916163871647217867711176893160701118870991637172205719520674622228244226836022590862241180919811821216123202491300329813015300132552234240332242618315771071327712313377208134773713317765133677668334777003327770713077917113779863478000936880691119938221241105493881128549411583811811995540612017240712037812212098640812116242512124412612169342912181838312261638412274512012312744712313813612355137412373446012381444312424246412437139812518912112534547912553148112576229712580829912592648212651649512676748012688850112738550212809039012836239112842939540034Hydrogen 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+215467087531578831848311162146326146454223149278017425022425442454710457618469470524110353271115353112562610856391075699100572010557421175963147603715560701576093161613015962321666483178660115266921016843188691018771001637168205719120674532197454220747222275252137532210755821275721607590170819522582181518243226841316284202249139195915524911915164120152811218128512246286122662871252122713257223133252941533030842329315423543184240132242405312424543207691229377136133772101347737233177804114779551327799032777991347783793457992913080019368803873108038830480722119938231249482338311055038811285594113280390115537398115539118115856336116205109119973406120193407120549122120593409121170424121171425122569418122615384122687125122758120123183135123218137123742459123743460125141454125188121125273136125359479125550481125730483125736297125809299126517495126717489126766480126823300126902501127213208128308506128361391128430395721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD1404150335386511011142113443127351466542229492779172835293107948071848131848192849026496031516795523810353341115360112546912354821255590135561011856961005738108582714159121475942151602415560721576076161638516469178677211768901607012188709716371742057197206740519874592228241226835922590852241181921612322249130062981301830013256223424043224261931577104132771201337720913477370331776503367766733477702332777091307791511377983347784063568000636880690119938251241105523881127501661128539411992912211995240612017140712083441912098440812115942512124212612125942912181738312261438412274212012313044712314113612341945512354937412373146012381244312382946412437039812518712112531929712534247912553048112580629912582549012592448212651549512676548012688550112727850712738350212808939012836039112842839581Glycerol 3-phosphateHMDB0000126Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).17989-41-2C0009343916215978GLYCEROL-3P388308DB02515OC[C@@H](O)COP(O)(O)=OC3H9O6PInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1AWUCVROLDVIAJX-GSVOUGTGSA-N[(2R)-2,3-dihydroxypropoxy]phosphonic acid172.0737172.013674532-0.7543-phosphoglycerol0-2FDB0218001-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acidPW_C000081Glyc1P10438147521488422115586295107629610884121629122170106531881254615112550223153192493481417424663184246731578030111780523507837234578378132799521348180825393826124947893841105533881106363911158401181207561221212974181213451211214154331233531351238674541239744681257882971259784891259912991272432051274315061031Palmityl-CoAHMDB0001338Palmityl-CoA, also known as palmitoyl CoA or CoA, palmitoyl, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Palmityl-CoA has been found throughout most human tissues, and has also been primarily detected in urine. Within the cell, palmityl-CoA is primarily located in the cytoplasm and mitochondria. In humans, palmityl-CoA is involved in cardiolipin biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) pathway, cardiolipin biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, cardiolipin biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, and cardiolipin biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) pathway. Palmityl-CoA is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/16:0/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(16:0/14:1(9Z)/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(a-25:0/i-14:0/16:0) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway. Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.1763-10-6C001541566715525PALMITYL-COA14902CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(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=C2NC37H66N7O17P3SInChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32?,36-/m1/s1MNBKLUUYKPBKDU-TZIIWEFPSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexadecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid1005.9431005.344873947-2.769palmitoyl-coa0-4FDB022562Hexadecanoyl coa;Hexadecanoyl coenzyme a;Palmitoyl coa;Palmitoyl coenzyme a;Palmitoyl-coa;Palmitoyl-coenzyme a;Palmityl-coa;Palmityl-coenzyme a;S-hexadecanoate;S-hexadecanoate coa;S-hexadecanoate coenzyme a;S-hexadecanoic acid;S-palmitoylcoenzyme a;CoA(16:0)PW_C001031COA16:08753880228901716471420901020962522910252441046958162697019971291637201160912317091291889214195255034977219134772273297789311278045332780491327854911579257333818443319076721095706383971203821085972881111033891142053901202283841206644071213564051214041231214111241229011211229143991232781191239153761239634471239701181255764801255894841260264811260284781262082991271063911274782061274802091277703881288473981099Coenzyme 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_C001099CoA2114386884538792289217240759241422459528132928623133421133511846181046295848421448655448796523210252471045280103547712457341085777101602315560751616384164681786930160696116269731997083188710816372931987347210745822282291519081226909022491241709215195130132991531824925488494261631576907293771191337722213477230329772921117755013277555334775631127763333677672129779961157804733278056350784133357856713079259333799743318000536880620118806273748063511980665376938283829383438398674288110555389110561390115842399115847398119951406120147405120231384120305122120634407120762117121406123121421433121521125121666429121682408121714414122404422122741120122904121122960135123965447123979468124079136124220464124265450124974375125341479125509478125579480125592484125634297126084481126549491126560482126746300126884501127046209127109391127301205127540206127667388128121508128133502128340395445991-palmitoylglycerone 3-phosphateHMDB00621901-Palmitoyl-dihydroxyacetone-phosphate, also known as palmitoyl glycerone phosphate or hexadecanoyl dihydroxyacetone phosphoric acid, belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position. 1-Palmitoyl-dihydroxyacetone-phosphate is considered to be a practically insoluble (in water) and relatively neutral molecule. 1-Palmitoyl-dihydroxyacetone-phosphate can be biosynthesized from dihydroxyacetone..17868CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=OC19H37O7PInChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h2-17H2,1H3,(H2,22,23,24)MLWXSIMRTQAWHY-UHFFFAOYSA-N[3-(hexadecanoyloxy)-2-oxopropoxy]phosphonic acid408.4666408.22769005-5.462palmitoylglycerone phosphate0-21-palmitoylglycerone 3-phosphate;Hexadecanoic acid 2-oxo-3-(phosphonooxy)propyl ester;Hexadecanoyl dihydroxyacetone phosphate;Palmitoyl dihydroxyacetone phosphate;Palmitoyl glycerone phosphate;Palmitoylglycerone phosphatePW_C0445991PalG3P146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1ACFIXJIJDZMPPO-NCHANQSKSA-N{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid745.4209745.091102105-2.149[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid0-4FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH185819037781079658211883721609291615494687314793144797145310111578910859721476128159627135677911770681887103163715420572051607315213734521075592127591170819422582191518421224118121981189321112006222121501641224528612596226126482494234331543746322769112937716613277385331773943327746013077504112775111157762333680712119113164941201054071204254051204521221206161231211411251212754291214021241214833831230593761230861351232414471237121361238464641239611181240413981254724811256962971262142991265294951270092061275723881281013903904LPA(16:0/0:0)HMDB0007853LPA(16:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.C00681641970115799ACYL-SN-GLYCEROL-3P4925335CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=OC19H39O7PInChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)YNDYKPRNFWPPFU-UHFFFAOYSA-N[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid410.4825410.243340114-5.233PLPA0-2FDB0250461-hexadecanoyl-phosphatidic acid;1-palmitoyl lysophosphatidate;1-palmitoyl lysophosphatidic acid;1-palmitoyl-glycero-3-phosphate;1-palmitoylglycerol 3-phosphate;1-palmitoyllysophosphatidate;1-palmitoyllysophosphatidic acid;2-hydroxy-3-(phosphonooxy)propyl ester hexadecanoate;2-hydroxy-3-(phosphonooxy)propyl ester hexadecanoic acid;Lpa(16:0);Lpa(16:0/0:0);Lysopa(16:0/0:0);Lysophosphatidic acid(16:0);Lysophosphatidic acid(16:0/0:0);(2r)-2-hydroxy-3-(phosphonooxy)propyl palmitate;1-hexadecanoyl-sn-glycero-3-phosphate;(2r)-2-hydroxy-3-(phosphonooxy)propyl palmitic acidPW_C003904LPA16:0147749149342208610213458912517015323249254922278046332780553507851933178527345818113299385438293855383108547288110593389110594390115920399115921398121302418121405123121419433123872454123964447123978468125969495125983489127436506143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium744.4129744.083277073-2.2791-[(2R,3R,4S,5R)-5-{[({[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-3FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP1838191376857801082418839216112916174946853147961448011453081115790108601714761321596273356778117706918871051637152205720616073172137346210756221275891708197225822015184192241181119811897211120082221215216412249286125972261265024942344315437453227691329377164132773843317739633277461130775151157762433677814334778701128071311911316594120106407120429405120450122120604408120618123121142125121277429121401124121485383123063376123084135123229374123243447123713136123848464123960118124043398125473481125694297125743482126215299126528495127010206127225502127570388128100390145Palmitic acidHMDB0000220Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.57-10-3C0024998515756CPD-8475960DB03796CCCCCCCCCCCCCCCC(O)=OC16H32O2InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)IPCSVZSSVZVIGE-UHFFFAOYSA-Nhexadecanoic acid256.4241256.240230268-5.801palmitic acid0-1FDB0116791-hexyldecanoate;1-hexyldecanoic acid;1-pentadecanecarboxylic acid;C16 fatty acid;Cetylic acid;Edenor c16;Emersol 140;Emersol 143;Glycon p-45;Hexadecanoate;Hexadecanoic acid;Hexadecanoic acid palmitic acid;Hexadecoate;Hexadecoic acid;Hexadecylic acid;Hexaectylic acid;Hydrofol;Hydrofol acid 1690;Hystrene 8016;Hystrene 9016;Industrene 4516;Kortacid 1698;Loxiol ep 278;Lunac p 95;Lunac p 95kc;Lunac p 98;N-hexadecanoate;N-hexadecanoic acid;N-hexadecoate;N-hexadecoic acid;Pam;Plm;Palmitate;Palmitic acid;Palmitinate;Palmitinic acid;Palmitinsaeure;Palmitoate;Palmitoic acid;Pentadecanecarboxylate;Pentadecanecarboxylic acid;Prifac 2960;Prifrac 2960;Pristerene 4934;Univol u332;C16:0;Ch3-[ch2]14-cooh;1-pentadecanecarboxylate;Cetylate;Hexadecylate;Hexaectylate;Hexadecanoate (n-c16:0);FA(16:0)PW_C00014516:0876387822217714218122185152843292898852491046447105644810765151086957160697519971301638311210922317012916151129182264252332042524318425253157723232977655336778611327789411278060115780611141202443821206654071214274051214294091214311241216994291229183991232791191239853761239871371239891181242494641255944841266372991271223891282133881420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765133149DG(16:0/16:0/0:0)HMDB0007098DG(16:0/16:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.30334-71-5C00165644078237189DIACYLGLYCEROL559127[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC35H68O5InChI=1S/C35H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36H,3-32H2,1-2H3/t33-/m0/s1JEJLGIQLPYYGEE-XIFFEERXSA-N(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl hexadecanoate568.9114568.506675286-7.451diacylglycerol00FDB0242921,2-dipalmitoyl-rac-glycerol;Dag(16:0/16:0);Dag(32:0);Dg(16:0/16:0);Dg(32:0);Diacylglycerol;Diacylglycerol(16:0/16:0);Diacylglycerol(32:0);Diglyceride;(s)-1-(hydroxymethyl)ethane-1,2-diyl dipalmitate;1,2-dihexadecanoyl-sn-glycerol;Dg(16:0/16:0/0:0);(s)-1-(hydroxymethyl)ethane-1,2-diyl dipalmitic acidPW_C003149DG32:0152543210910214358218415913616092241709259195127811511529928515385497803633278040350780591147853535681813331938583831105973901156723981213184191213911231213964331214264091238884551239504471239554681239841371259994901274505071104PhosphateHMDB0001429Phosphate 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_C001104Pi244848814581818831298031763141767492500102729472737463129293166723636613851234249224475315031275158752079752161005317111535111253811035447120554312955731335605135562510856936584814358551465911147594115160401556100161629410764871786691101671411768421886889160716120571892067212211730619873892107402212743616374752228196225825822710118241101342571174813211761115117732131190417011927164120142811272829013263223348191742255304423503154243531843692322770182537719429377217134779403367796613078048332780573297824535378669331800223688927930893831383947963841105583901106403911132359411584539811620610911998240612006912212069940712105712412121612512126842912135212112140912312142338212185240512330411912362111812378613612383846412396844712398139912440537612494847212536247912544629712577448112595429912622147812659430012660429812672348412690450112741338812778320912816639512817751312831538957Cytidine 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_C000057CTP42723115082718257661015800108707718875931609137195914221312194164125102881528515115317249153422215374183475917426503157731512878448111787331327994913479957130799643298041617094784384948121259481738298677223110633391113268395113273389115525136115530399120328410120854122121340121122212124122983444123434135124764118125654485125840297126374299127292205127935388531PA(16:0/16:0)HMDB0000674PA(16:0/16:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.7091-44-3C0041644606673246L-PHOSPHATIDATE393518[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCC35H69O8PInChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1PORPENFLTBBHSG-MGBGTMOVSA-N[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid648.903648.47300618-6.742dipalmitoyl0-2FDB0221751,2-di-o-palmitoyl-3-sn-glyceryl-o-phosphorate;1,2-di-o-palmitoyl-3-sn-glyceryl-o-phosphoric acid;1,2-dihexadecanoyl-rac-phosphatidic acid;1,2-dipalmitoyl-3-sn-phosphatidate;1,2-dipalmitoyl-3-sn-phosphatidic acid;1,2-dipalmitoyl-sn-glycerol 3-phosphate;1,2-dipalmitoyl-sn-glycerol-3-phosphorate;1,2-dipalmitoyl-sn-glycerol-3-phosphoric acid;Dipalmitoyl-l-a-phosphatidate;Dipalmitoyl-l-a-phosphatidic acid;Dipalmitoyl-l-alpha-phosphatidate;Dipalmitoyl-l-alpha-phosphatidic acid;Dipalmitoylphosphatidate;Dipalmitoylphosphatidic acid;L-a-dipalmitoyl-phosphatidate;L-a-dipalmitoyl-phosphatidic acid;L-a-dipalmitoylphosphatidate;L-a-dipalmitoylphosphatidic acid;L-alpha-dipalmitoyl-phosphatidate;L-alpha-dipalmitoyl-phosphatidic acid;L-alpha-dipalmitoylphosphatidate;L-alpha-dipalmitoylphosphatidic acid;Pa(32:0);Phosphatidic acid(16:0/16:0);Phosphatidic acid(32:0);1,2-dipalmitoyl-sn-glycerol-3-phosphate;Dipalmitoyl phosphatidic acid;Pa(16:0/16:0)PW_C000531PA32:01480491494421535142107102140586912197691318991301889138195152981511532524936244223624617780383327804235078520331785283457853711585376329853771349385738394782382947853841085492881085502231105963901106983891106993911159233981213034181213214051213931231213984331216623991216641211238734541238913761239524471239574681259704951259844891260024781274375061274532091189CDPHMDB0001546CDP, also known as 5'-cdp, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. CDP is soluble (in water) and a moderately acidic compound (based on its pKa). CDP has been primarily detected in blood. Within the cell, CDP is primarily located in the mitochondria, nucleus and cytoplasm. In humans, CDP is involved in the pyrimidine metabolism pathway. CDP is also involved in several metabolic disorders, some of which include dihydropyrimidinase deficiency, UMP synthase deficiency (orotic aciduria), the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, and Beta ureidopropionase deficiency. Cytidine 5\'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.63-38-7C00112613217239CDP5902NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H15N3O11P2InChI=1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1ZWIADYZPOWUWEW-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]phosphonic acid403.1764403.018181361-1.606CDP0-2FDB022683Cdp;Cytidine-5'-diphosphate;Cytidine-diphosphate;5'-cdp;Cytidine 5'-diphosphate;Cytidine 5'-diphosphoric acid;Cytidine 5'-pyrophosphate;Cytidine diphosphate;Cytidine, 5'-(trihydrogen pyrophosphate);Cytidine 5'-pyrophosphoric acid;Cytidine diphosphoric acid;Cytidine, 5'-(trihydrogen pyrophosphoric acid);Cytidine-5'-diphosphoric acidPW_C001189CDP2733291401959143213787351321222151241247671181263772991279393881201CDP-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-Etala3384181529028815343224089549785711307996632979978331948203829485638311327638911553339911574939812260312512517513612675030012834439564Cytidine 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_C000064CMP11518251214273423386184972565768101580210870791887595160914724991512249257195121961641221015115274285153363081537349348151742652315784491117848811578573130787361327995313479969331804211709479138494821383986802231106373911132773901155353981208551221213461211222161241224874051226051251234351351247681181250533761251771361258412971263782991266414781267523001272932051279403881282172091283463954971PE(16:0/16:0)HMDB0008923PE(16:0/16:0) is a phosphatidylethanolamine. It is a glycerophospholipid in which a phosphorylethanolamine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphoethanolamines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PE(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.923-61-5C0035044546873005L-1-PHOSPHATIDYL-ETHANOLAMINE393103[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCCC37H74NO8PInChI=1S/C37H74NO8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(39)43-33-35(34-45-47(41,42)44-32-31-38)46-37(40)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35H,3-34,38H2,1-2H3,(H,41,42)/t35-/m1/s1SLKDGVPOSSLUAI-PGUFJCEWSA-N(2-aminoethoxy)[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid691.972691.515205345-6.862DPPE00C003501,2-dipalmitoyl-rac-glycero-3-phosphoethanolamine;Gpetn(16:0/16:0);Gpetn(32:0);Pe(16:0/16:0);Pe(32:0);Phophatidylethanolamine(16:0/16:0);Phophatidylethanolamine(32:0);1,2-dihexadecanoyl-sn-glycero-3-phosphoethanolamine;1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine zwitterion;2-ammonioethyl (2r)-2,3-bis(palmitoyloxy)propyl phosphatePW_C004971PE161555141566499149249926016397691951529715115321285153873091539217785381157854333180737253888952318905513489056361948423839484438494845386115673398115676121115677401121324405123894376126005478126015495127456209127467390149O-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_C000149Ethamp2118104978872142121217928515328308153551511537627885333279965362799771329481838594855124113274396115531400115747118122067123124618447126222298127784513170PyrophosphateHMDB0000250The 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_C000170Ppi12235463842923735328822212173162049241059281529417514486854503489525210452941015409117542410354331185458120554811155591325584133560613556551085879107623916669781997073188713416372721607312198731821382751518283210118691611200222212041164123152251232324912512288125792261269529015219306153751834760174256131542697318772353297731712877635336784163357892833179153112799501347995813080047372804171708563019478638494814125948193829867822311063439111327039511327538911552713611553239911993412212001712412003240612033041012093640712126142912134112112148638312240742212298544412350211912383146412404439812497737512532429712539529912541047912559748412565648512587648112655249112686920512693538812695050112733720612812450896EthanolamineHMDB0000149Ethanolamine 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_C001034ADP2341348415224821380159631597831061141518219014921041821131021615824085924352727284727364628552931657236356144002344763147709150362651577520897521710053151115349112539210354461205544129557213356241085741117576410158491435856146587810758991475926151605015561111616231166649517867009468411886872160715920571872067208210722621372312117300198730321673912177410218743316374832228187225118512771190517012013281121802851326222315329308423283154239831342622322426963187702925377087132772161347730632977472333776633367803933278043350781701287821535178244353784143357849511578705331788491307892033480030368806221188065113580676119948271241132833881162041091199441221199944061201564071203183821203664121212484291213941231213994331214724081218993831219764101220641251220854051224054221224454351229733991230134461238184641239534471239584681240303741244523981245294441246151361246363761249474721249753751250124701253342971253734791254922991255174811256454841261254851262193001262354951262424781265504911265974991269155011277335161277803951277973901278032091281225081281685171283133892009(2E)-Hexadecenoyl-CoAHMDB0003945(2E)-Hexadecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme enoyl-CoA hydratase [EC:4.2.1.17]; (2E)-Hexadecenoyl-CoA is also the substrate of the enzyme trans-2-enoyl-CoA reductase [EC:1.3.1.38], in the fatty acid elongation pathway in mitochondria. (PMID: 1278159, KEGG).4460-95-1C05272461731766152626332261CCCCCCCCCCCCCC=CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC37H64N7O17P3SInChI=1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h16-17,24-26,30-32,36,47-48H,4-15,18-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)JUPAQFRKPHPXLD-UHFFFAOYSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(2E)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid1003.931003.329225797-2.889(E)-2-hexadecenoyl-coa0-4FDB023264(2e)-hexadecenoyl-coa;(2e)-hexadecenoyl-coenzyme a;Trans-2-hexadecenoyl-coa;Trans-2-hexadecenoyl-coenzyme a;(e)-c16:1 n-14-coa;(e)-hexadec-2-enoyl-coa tetraanion;(e)-hexadec-2-enoyl-coenzyme a tetraanion;(e)-hexadec-2-enoyl-coenzyme a(4-);Trans-2-hexadecenoyl-coa(4-);Trans-2-hexadecenoyl-coenzyme a tetraanion;Trans-2-hexadecenoyl-coenzyme a(4-);Trans-c16:1 n-14-coa;Trans-hexadec-2-enoyl-coa(4-)PW_C002009(E)-C168743894179044523510369641617128163772241337789211212023440612066340712290712012327711912558247912711250110942glycerol-3-phosphate dehydrogenaseQ00055
Catalyzes the production and accumulation of glycerol during hyperosmotic stress conditions. Glycerol acts as a osmoregulator that prevents loss of water and turgor of the cells.
GPD1291.1.1.8780521010943glycerol-3-phosphate dehydrogenase GPD2P41911
Catalyzes the production of glycerol under anaerobic growth conditions. Glycerol production serves as a redox sink by consuming the excess cytosolic NADH during anaerobic metabolism.
GPD2,GPD3291.1.1.8780421010658Glycerol-3-phosphate O-acyltransferase 2P36148
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
GTP2292.3.1.15; 2.3.1.4276801607687213780221091261701065418810659Glycerol-3-phosphate O-acyltransferase 1P32784
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
SCT1292.3.1.15; 2.3.1.4276791607686213780321091271701065518810944glycerol-3-phosphate O-acyltransferase / dihydroxyacetone phosphate acyltransferaseP36148
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
GPT2, GAT1292.3.1.15; 2.3.1.42780621091281701065618810660NADPH-dependent 1-acyldihydroxyacetone phosphate reductaseP40471
Can convert acyl and alkyl dihydroxyacetone-phosphate (DHAP) into glycerolipids and ether lipids, respectively. Required for the biosynthesis of phosphatidic acid via the DHAP pathway, where it reduces 1-acyl DHAP to lysophosphatidic acid (LPA). Required for spore germination.
AYR1291.1.1.1017788160780121010661acyl-CoA:lyso-phospholipid acyltransferaseQ08548
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phospholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol.
ALE1292.3.1.23; 2.3.1.5176831607688213779821091311888040517010662Lipase 4P36165
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL4293.1.1.376851607692213779921091321888040617010663Probable 1-acyl-sn-glycerol-3-phosphate acyltransferaseP33333
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein.
SLC1292.3.1.5176821607689213780021091331888040717010664Lipase 5Q12043
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL5293.1.1.376841607691213779721091341888040817010665Lysophosphatidic acid:oleoyl-CoA acyltransferase 1Q06508
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
LOA1292.3.1.5176811607690213779621091351888040917010945Phosphatidic acid phosphohydrolase 1P32567
Mg(2+)-dependent phosphatidate (PA) phosphatase which catalyzes the dephosphorylation of PA to yield diacylglycerol. Required for de novo lipid synthesis and formation of lipid droplets. Controles transcription of phospholipid biosynthetic genes and nuclear structure by regulating the amount of membrane present at the nuclear envelope. Involved in plasmid maintenance, in respiration and in cell proliferation.
PAH1293.1.3.47793160779421010946CTP-dependent diacylglycerol kinase 1Q12382
Involved in pre-tRNA splicing (By similarity). CTP-dependent diacylglycerol kinase that catalyzes the phosphorylation of diacylglycerol (DAG) to phosphatidate (PA). Controls phosphatidate levels at the nuclear envelope. Counteracts the activity of PAH1/SMP2. Involved in the resistance to nickel chloride and nalidixic acid. May be involved in vesicle trafficking between the endoplasmic reticulum and the Golgi apparatus.
DGK1292.7.1.17477921607795210914119591442132548Ethanolaminephosphotransferase 1Q9C0D9Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the formation of phosphatidylethanolamine via 'Kennedy' pathway.
HMDBP07306EPT12p23.3AB05151112.7.8.17759160778921410947phosphoethanolamine cytidylyltransferaseP33412
Ethanolamine-phosphate cytidylyltransferase which catalyzes the second step of phosphatidylethanolamine biosynthesis. Involved in the maintenance of plasma membrane and required for proper sporulation.
ECT1292.7.7.14779016010948Ethanolamine kinaseQ03764
Catalyzes the committed step of phosphatidylethanolamine synthesis via the CDP-ethanolamine pathway. Also exhibits choline kinase activity but its preferred substrate is ethanolamine.
EKI1292.7.1.8277911604720glycerol-3-phosphate dehydrogenase18PW_P004720119021094211903109434341Glycerol-3-phosphate O-acyltransferase 18PW_P004341114041065811405106594721glycerol-3-phosphate O-acyltransferase / dihydroxyacetone phosphate acyltransferase18PW_P004721119041094443421-acyl dihydroxyacetone phosphate reductase18PW_P00434211406106604343oleoyl-CoA: lysophosphatidate acyltransferase18PW_P004343114071066111408106621140910663114101066411411106654722Phosphatidic acid phosphohydrolase 118PW_P00472211905109454723CTP-dependent diacylglycerol kinase 118PW_P00472311906109464719bifunctional diacylglycerol cholinephosphotransferase/ethanolaminephosphotransferase 18PW_P0047191190125484724phosphoethanolamine cytidylyltransferase18PW_P00472411907109474725Ethanolamine kinase18PW_P00472511908109486986falsePW_R006986Right28774426311Compoundfalse2877511441Compoundfalse28776400341Compoundfalse287777211Compoundfalse28778811Compoundfalse696347201.1.1.86987falsePW_R006987Both28779426311Compoundfalse2878010311Compoundfalse2878110991Compoundfalse28782445991Compoundfalse696443412.3.1.15,2.3.1.42696547212.3.1.15,2.3.1.426988falsePW_R006988Right28783445991Compoundfalse287841461Compoundfalse28785400341Compoundfalse2878639041Compoundfalse287871431Compoundfalse696643426993falsePW_R006993Right2880531491Compoundfalse28806571Compoundfalse288075311Compoundfalse28808400341Compoundfalse2880911891Compoundfalse697147232.7.1.1746994falsePW_R006994Right2881031491Compoundfalse2881112011Compoundfalse28812641Compoundfalse28813400341Compoundfalse2881449711Compoundfalse697247196995falsePW_R006995Right288151491Compoundfalse28816400341Compoundfalse28817571Compoundfalse2881812011Compoundfalse288191701Compoundfalse697347242.7.7.146996falsePW_R006996Right28820961Compoundfalse288214141Compoundtrue2882210341Compoundtrue28823400341Compoundtrue288241491Compoundfalse697447252.7.1.82179646falsePW_R179646Right678000811Compoundfalse67800120091Compoundfalse67800210991Compoundfalse678003445991Compoundfalse16952843426991falsePW_R006991Right2879739041Compoundfalse287981451Compoundfalse287995311Compoundfalse2880010991Compoundfalse696943436992falsePW_R006992Right288015311Compoundfalse2880214201Compoundtrue2880331491Compoundfalse2880411041Compoundtrue697047223.1.3.481351426313false106645710regular10011081352114460false119258710regular5030813534003455false126861710regular78788135472159false171259410regular503081355813false180745410regular1001108135610313false92159210regular10010081357109985false93994210regular503081358445993false1064103710regular1001208135914662false1294117910regular5030813604003455false1175115910regular78788136139043false1810105310regular1001008136214361false1734118310regular5030813731453false1915117310regular10010081375109985false248094010regular503081380142049false2857121110regular78788138131493false2544164510regular10010081382110446false2874152810regular444381383573false2414150010regular100110813845313false2540104510regular100100813854003455false2685120610regular78788138611893false2403119510regular1001008138712013false2034189010regular10011081388643false2710240010regular100110813894003455false2425240110regular78788139049713false2553259010regular100100813911493false1384189210regular100110813924003455false1500180710regular787881393573false1489200010regular1001108139417045false1972180210regular634381395963false744190010regular1001008139641442false869184010regular503081397103443false1294183410regular5030813984003455false1305200910regular7878268209920093false195751910regular1001202682100109985false198489710regular503038664109422102false13674398subunitregular1507038665109432102false14374748subunitregular1507038666106582102false9618098subunitregular1507038667106592102false9517398subunitregular1507038668109442102false103176920subunitregular1507038669106602102false142910658subunitregular1507038679106612102false224010938subunitregular1507038680106622102false210510938subunitregular1507038681106632102false222510138subunitregular1507038682106642102false210510188subunitregular1507038683106652102false218010638subunitregular1507038686109452102false272013608subunitregular1507038687109462102false251913678subunitregular150703868825482142false252922758subunitregular1507038689109471602false168919118subunitregular1507038690109481602false101919138subunitregular15070949592106602false17877288subunitregular150703147147202250379883866437989386653147243412250379903866637991386673147347212250379923866831474434222503799338669314784343225038003386793800438680380053868138006386823800738683314804722225038010386863148147232250380113868731482471922503801238688314834724225038013386893148447252250380143869080408643422250945422949592116779M1166 512 C1196 512 1407 509 1437 509 5false18116780M1242 602 C1246 531 1312 510 1437 509 5false18116781M1346 656 C1352 542 1356 510 1437 509 5false18116782M1712 609 C1709 532 1663 509 1587 509 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false116783M1807 509 C1777 509 1617 509 1587 509 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false116784M1116 567 C1116 597 1111.5 869.5 1111.5 899.5 5false18trueM 704.9468550441649 528.261556296296 L 690 527 L 696.3808877211858 540.5751343230784false116785M971 692 C1127 696 1110.5 706.5 1111.5 924.5 5false18trueM 704.9468550441649 528.261556296296 L 690 527 L 696.3808877211858 540.5751343230784false116786M964 942 C1083 945 1111.5 939.5 1111.5 909.5 5false18trueM 704.9468550441649 528.261556296296 L 690 527 L 696.3808877211858 540.5751343230784false116787M1114 1037 C1114 1007 1111.5 929.5 1111.5 899.5 5false18trueM 704.9468550441649 528.261556296296 L 690 527 L 696.3808877211858 540.5751343230784false116788M1164 1097 C1194 1097 1399 1100 1429 1100 5false18116789M1348 1194 C1348 1105 1399 1100 1429 1100 5false18116790M1253 1198 C1254 1103 1399 1100 1429 1100 5false18116791M1810 1103 C1780 1103 1609 1100 1579 1100 5false18trueM 444.94685504416486 546.261556296296 L 430 545 L 436.38088772118584 558.5751343230784false116792M1734 1198 C1728 1102 1609 1100 1579 1100 5false18trueM 444.94685504416486 546.261556296296 L 430 545 L 436.38088772118584 558.5751343230784false116819M2594 1645 C2595 1579 2598 1471 2594 1437 5false18116820M2464 1500 C2598 1500 2594 1467 2594 1437 5false18116821M2590 1145 C2590 1188 2593 1304 2594 1367 5false18trueM 1959.9468550441647 1302.261556296296 L 1945 1301 L 1951.380887721186 1314.5751343230784false116822M2724 1284 C2626 1285 2594 1337 2594 1367 5false18trueM 1959.9468550441647 1302.261556296296 L 1945 1301 L 1951.380887721186 1314.5751343230784false116823M2453 1295 C2580 1296 2594 1337 2594 1367 5false18trueM 1959.9468550441647 1302.261556296296 L 1945 1301 L 1951.380887721186 1314.5751343230784false116824M2594 1745 C2594 1775 2604 2245 2604 2275 5false18116825M2084 2000 C2278 1999 2604 2245 2604 2275 5false18116826M2760 2400 C2610 2402 2604 2375 2604 2345 5false18trueM 1959.9468550441647 1341.261556296296 L 1945 1340 L 1951.380887721186 1353.5751343230784false116827M2464 2401 C2539 2400 2604 2375 2604 2345 5false18trueM 1959.9468550441647 1341.261556296296 L 1945 1340 L 1951.380887721186 1353.5751343230784false116828M2603 2590 C2603 2560 2604 2375 2604 2345 5false18trueM 1959.9468550441647 1341.261556296296 L 1945 1340 L 1951.380887721186 1353.5751343230784false116829M1484 1947 C1514 1947 1659 1946 1689 1946 5false18116830M1578 1846 C1578 1942 1659 1946 1689 1946 5false18116831M1589 2055 C1587 1950 1659 1946 1689 1946 5false18116832M2034 1945 C2004 1945 1869 1946 1839 1946 5false18trueM 1448.9468550441647 1667.261556296296 L 1434 1666 L 1440.380887721186 1679.5751343230784false116833M1972 1823.5 C1972 1944.5 1869 1946 1839 1946 5false18trueM 1448.9468550441647 1667.261556296296 L 1434 1666 L 1440.380887721186 1679.5751343230784false116834M844 1950 C874 1950 989 1948 1019 1948 5false18116835M919 1855 C922 1950 989 1948 1019 1948 5false18116836M1294 1849 C1292 1945 1199 1948 1169 1948 5false18trueM 1088.9468550441647 1667.261556296296 L 1074 1666 L 1080.380887721186 1679.5751343230784false116837M1305 2048 C1302 1952 1199 1948 1169 1948 5false18trueM 1088.9468550441647 1667.261556296296 L 1074 1666 L 1080.380887721186 1679.5751343230784false116838M1384 1947 C1354 1947 1199 1948 1169 1948 5false18trueM 1088.9468550441647 1667.261556296296 L 1074 1666 L 1080.380887721186 1679.5751343230784false3666040M1857 564 C1857 594 1862 698 1862 728 5false183666041M2007 639 C1858 647 1862 698 1862 728 5false183666042M2009 897 C1870 906 1862 828 1862 798 5false18trueM 436.94685504416486 690.261556296296 L 422 689 L 428.38088772118584 702.5751343230784false3666043M1142 1037 C1144 1000 1144 1005 1143 954 C1187 952 1794 949 1866 949 C1865 907 1864 898 1862 798 5false18trueM 436.94685504416486 690.261556296296 L 422 689 L 428.38088772118584 702.5751343230784false3666044M1910 1103 C1940 1103 2150 1098 2180 1098 5false183666045M2015 1223 C2013 1104 2150 1098 2180 1098 5false183666046M2540 1095 C2510 1095 2360 1098 2330 1098 5false18trueM 1304.9468550441647 936.261556296296 L 1290 935 L 1296.380887721186 948.5751343230784false3666047M2480 955 C2480 1098 2360 1098 2330 1098 5false18trueM 1304.9468550441647 936.261556296296 L 1290 935 L 1296.380887721186 948.5751343230784false3666048M2640 1095 C2672 1097 2768 1097 2792 1099 C2795 1199 2794 1281 2795 1360 5false183666049M2896 1289 C2793 1288 2795 1330 2795 1360 5false183666050M2644 1695 C2667 1694 2775 1693 2800 1691 C2802 1653 2795 1530 2795 1430 5false18trueM 1304.9468550441647 1072.261556296296 L 1290 1071 L 1296.380887721186 1084.5751343230784false3666051M2896 1528 C2797 1527 2795 1460 2795 1430 5false18trueM 1304.9468550441647 1072.261556296296 L 1290 1071 L 1296.380887721186 1084.5751343230784false23965225069869239181351116779Left9239281352116780Left9239381353116781Left9239481354116782Right9239581355116783Right2376469633147123966225069879239681351116784Left9239781356116785Left9239881357116786Right9239981358116787Right237656964314722376669653147323967225069889240081358116788Left9240181359116789Left9240281360116790Left9240381361116791Right9240481362116792Right2376769663147423974225069939243181381116819Left9243281383116820Left9243381384116821Right9243481385116822Right9243581386116823Right2377469713148123975225069949243681381116824Left9243781387116825Left9243881388116826Right9243981389116827Right9244081390116828Right2377569723148223976225069959244181391116829Left9244281392116830Left9244381393116831Left9244481387116832Right9244581394116833Right2377669733148323977225069969244681395116834Left9244781396116835Left9244881397116836Right9244981398116837Right9245081391116838Right2377769743148479855922501796463227455813553666040Left322745626820993666041Left322745726821003666042Right3227458813583666043Right754133169528804086798560225069913227459813613666044Left3227460813733666045Left3227461813843666046Right3227462813753666047Right754134696931478798561225069923227463813843666048Left3227464813803666049Left3227465813813666050Right3227466813823666051Right75413569703148015433643901.01.002904844971544183423141.01.002202902604384M280 371 C280 321 330 271 380 271 C1154 271 2159 271 2933 271 C2983 271 3033 321 3033 371 C3033 1085 3033 2014 3033 2728 C3033 2778 2983 2828 2933 2828 C2159 2828 1154 2828 380 2828 C330 2828 280 2778 280 2728 C280 2014 280 1085 280 371 1true62753.02557.04385M125 225 C125 175 175 125 225 125 C1090 125 2213 125 3078 125 C3128 125 3178 175 3178 225 C3178 1028 3178 2072 3178 2875 C3178 2925 3128 2975 3078 2975 C2213 2975 1090 2975 225 2975 C175 2975 125 2925 125 2875 C125 2072 125 1028 125 225 1true63053.02850.045068915Endoplasmic Reticulum2614389201.91.91601545069015Golgi apparatus22542178201.91.9160157346755368643722961177839#FFEEDE42097140673519922415224822082926275039#FFE6CC4678542