2576PathwayLysolipid Incorporation into ER PC(10:0/10:0)Lysolipids such as lysophosphatidylethanolamine, lysophosphatidylcholine, lysophosphatidylserine and lysophosphatidylinositol get transported into the cell through a phospholipid ATPase. Once in the cytosol they are incorporated into the ER membrane through a Ale1p transport membrane where phosphatidylcholine is generated.MetabolicPW002780CenterPathwayVisualizationContext306825003850#000099PathwayVisualization25392576Lysolipid Incorporation into ER PC(10:0/10:0)Lysolipids such as lysophosphatidylethanolamine, lysophosphatidylcholine, lysophosphatidylserine and lysophosphatidylinositol get transported into the cell through a phospholipid ATPase. Once in the cytosol they are incorporated into the ER membrane through a Ale1p transport membrane where phosphatidylcholine is generated.Metabolic1833267917951629Riekhof WR, Wu J, Gijon MA, Zarini S, Murphy RC, Voelker DR: Lysophosphatidylcholine metabolism in Saccharomyces cerevisiae: the role of P-type ATPases in transport and a broad specificity acyltransferase in acylation. J Biol Chem. 2007 Dec 21;282(51):36853-61. doi: 10.1074/jbc.M706718200. Epub 2007 Oct 21.2576Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404Cardiomyocyte CL:00007468Beta cellCL:00006397Epithelial CellCL:00000666MyocyteCL:00001871Homo sapiens9606EukaryoteHuman2Bacteria2ProkaryoteBacteria3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse17Rattus norvegicus10116EukaryoteRat19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia45Bos taurus9913EukaryoteCattle10Drosophila melanogaster7227EukaryoteFruit fly29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast51Picea sitchensis3332EukaryoteSitka spruce1CytosolGO:00058293Mitochondrial MatrixGO:00057595CytoplasmGO:000573714Mitochondrial Outer MembraneGO:00057412MitochondrionGO:000573915NucleusGO:00056344PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577831Periplasmic SpaceGO:000562011Extracellular SpaceGO:000561535ChloroplastGO:000950712Mitochondrial Inner MembraneGO:000574332Inner MembraneGO:00702586LysosomeGO:000576416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520236MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259719sarcoplasmic reticulumGO:001652924Mitochondrial Intermembrane SpaceGO:000575817NucleoplasmGO:000565439Mitochondrial membraneGO:003196626Golgi apparatus membraneGO:00001392Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971828StomachBTO:00013071552611HeartBTO:000056273109MuscleBTO:0000887141182111PW_BS0000024311PW_BS0000048511PW_BS00000816212PW_BS000016221411PW_BS00002213121PW_BS0000133211515PW_BS0000325411PW_BS000005397113PW_BS0000393211PW_BS000003181311PW_BS000018101711PW_BS00001049711PW_BS00004914101PW_BS0000145811411PW_BS000058592711PW_BS00005927151PW_BS00002746114PW_BS00004629111PW_BS0000296618518PW_BS00006672513PW_BS000072612517PW_BS0000615181PW_BS000051231511PW_BS000023311511PW_BS000031918511PW_BS000091541315PW_BS000054892PW_BS000089261115PW_BS000026711PW_BS000007971521PW_BS000097100521PW_BS0001001041431PW_BS000104101531PW_BS0001011115121PW_BS0001111122121PW_BS000112103331PW_BS000103117131PW_BS0001171181171PW_BS0001181203171PW_BS00012012915121PW_BS0001291321121PW_BS0001321333121PW_BS0001331355171PW_BS00013510813PW_BS00010814315191PW_BS0001431465191PW_BS000146107313PW_BS0001071471241PW_BS000147151141PW_BS0001511553241PW_BS0001551613181PW_BS00016116611PW_BS0001661783211PW_BS000178188118PW_BS0000241601181PW_BS00016019914181PW_BS000024205561PW_BS000024206261PW_BS00002421013181PW_BS0000242137181PW_BS0000242111018PW_BS0000241985181PW_BS0000242164181PW_BS0000242171518PW_BS00002421815181PW_BS0000241632181PW_BS000163222341PW_BS0000241901118PW_BS0000242253541PW_BS0000242771218PW_BS00002417018PW_BS0001702811251PW_BS0000241644PW_BS0001642851041PW_BS000024226441PW_BS0000242905491PW_BS0000242231241PW_BS0000243081011PW_BS000024315123PW_BS0000243221231PW_BS0000243183123PW_BS000024253541PW_BS00002413412121PW_BS00013432914121PW_BS0000283331212PW_BS0000283361121PW_BS00002833217121PW_BS000028350114121PW_BS00002812815121PW_BS0001283511512PW_BS00002835325127PW_BS00002833527121PW_BS0000281151012PW_BS00011513013121PW_BS0001303317121PW_BS0000283344121PW_BS0000283683601PW_BS000028184121PW_BS0000241192171PW_BS00011911PW_BS000001124151PW_BS000124943PW_BS000094388161PW_BS000112109323PW_BS000109122551PW_BS000122406351PW_BS000115407251PW_BS0001153821451PW_BS000100412125PW_BS000115429151PW_BS0001151231751PW_BS00012343311451PW_BS000115408451PW_BS0001154101551PW_BS0001151251351PW_BS000125383751PW_BS000100405105PW_BS0001154222751PW_BS000115435155PW_BS00011539914171PW_BS0001134461217PW_BS0001154641171PW_BS00011544717171PW_BS000115468114171PW_BS0001153744171PW_BS00005344415171PW_BS00011513613171PW_BS0001363987171PW_BS0001133761017PW_BS00005347225177PW_BS00011537527171PW_BS0000534701517PW_BS0001152975101PW_BS0000244793101PW_BS0001152991101PW_BS0000244812101PW_BS00011548414101PW_BS00011548515101PW_BS00011530013101PW_BS0000244957101PW_BS0001154781010PW_BS00011549127101PW_BS0001154991510PW_BS000115501361PW_BS0001153891461PW_BS0001125161561PW_BS0001153951361PW_BS000113390761PW_BS000112209106PW_BS0000245082761PW_BS000115517156PW_BS0001159611PW_BS00000915111PW_BS0000152811611PW_BS000028204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS000060171211PW_BS0000177028511PW_BS0000703612011PW_BS0000363772113PW_BS00003793252011PW_BS000093105113PW_BS0001051136121PW_BS000113110231PW_BS000110126651PW_BS00012612711651PW_BS0001271141112PW_BS0001146131PW_BS000006140103PW_BS000140951721PW_BS0000951572241PW_BS00015715924PW_BS0001591802211PW_BS00018015284PW_BS000152207661PW_BS00002421425181PW_BS0000242156181PW_BS00002421217181PW_BS000024224241PW_BS00002416212181PW_BS0001622863641PW_BS0000242875341PW_BS0000242491341PW_BS0000242273441PW_BS00002465111PW_BS0000652916491PW_BS0000242924491PW_BS00002429817101PW_BS0000243016101PW_BS000024302116101PW_BS0000242941141PW_BS00002429341PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS0000243841251PW_BS0001003911261PW_BS000112232403PW_BS000024409115PW_BS0001154151851PW_BS0001154141551PW_BS0001154251355PW_BS00011512112171PW_BS0001214192551PW_BS00011543441051PW_BS000115436255PW_BS0001154436171PW_BS0001151371117PW_BS000137448116171PW_BS00011545118171PW_BS00011545015171PW_BS00011546013175PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS0001154824101PW_BS0001154831110PW_BS00011548718101PW_BS00011549025101PW_BS00011548012101PW_BS000115502461PW_BS000115208116PW_BS0000245041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS00004731323PW_BS000024241529PW_BS00002425715291PW_BS00002430412PW_BS000024422411PW_BS0000421873118PW_BS000024219314PW_BS00002422014PW_BS0000241951318PW_BS0000243125231PW_BS0000243201123PW_BS00002432711125PW_BS00002834524121PW_BS000028310312PW_BS0000244241155PW_BS0001154182451PW_BS00011545911175PW_BS00011545424171PW_BS00011548924101PW_BS0001155062461PW_BS0001152881441PW_BS00002430635511PW_BS000024372102PW_BS000028301711PW_BS000030509516PW_BS0000503093911PW_BS00002433817121PW_BS00002834695126PW_BS00002836139121PW_BS0000283863951PW_BS0001003973961PW_BS00011340139171PW_BS0001134131751PW_BS00011544917171PW_BS000115562611PW_BS000056414Adenosine 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_C000414ATP922146082661641422478137333279959343997632105182112102146492156142160582405592434272726462812293029663163723616613617514399234474314768914864545032895035265155752059752151005250104529110153131115346112539010354061175430118544312055421295556132556913356031355621108584614358541465876107589714759241516048155610916162301666493178683918868701606976199715720571842067209210722521372292117298198730221673902177408218743216374812227499190818622511847277119031701201028112039164121782851257822612691290132642231532730842326315426213224269431877028253772181347723332977468333776323367803733278041350781681287821435178240353784113357849411578850130788653317891933480028368800461848067411985629194826124113234941132823881162801091199141221199924061201544071202453821203624121212464291213921231213974331214714081219744101220651251220793831220834051224024221224444351229193991230094461238164641239514471239564681240293741245274441246161361246303981246343761249434721249723751250114701253042971253714791253922991255154811255954841261234851262203001262344951262404781265474911265964991269135011271233891277315161277813951277963901278012091281195081281675171420WaterHMDB0002111Water 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_C001420H2O5589491095139415131621448113526156242865210691207703382318838210943113774914655415904320182425322226786027274627781728052931437031647236346145983647273749419350302751567519597521410052279452361035297105531911153431135355112540211054701235483125549212655071275534130553711455411295591135560811856221085691657591405778101584114358531465877107589095591014759401516032155605915760871616123163613315962151621816664771786507180660015267131176840188688816071622057181207719320672112117228213723821472432157295198735021673882107401212746722274922247500190758817082012258237226841416292652611850277119221641201128112213285122502861226428712327249125202271263265126932901270529112715292130072981301930013025301130373021326122313327294153403084232731542695318436913227691429377019253771021327713113377215134773783317739733277471333775161157753633477628336777223377775934177816343779823477807132978235352782423537827035679113360800143688003937080591228806561199383038394794384110557390110639391115844398119879232119915122119963406120008407120046408120113124120365412120430405120438409120606415120794414121158425121240429121351121121381419121607434122118382122384436122753120122797374122804443123012446123064376123072137123131447123142136123162448123231451123384450123730460123810464123940455124165469124670399124938471124945472125305297125353479125386481125424482125480299125682483125707478125745487126054490126238495126273484126764480126896501126963502127017388127177208127199209127227504127506507127576515127836389128082395128176513108327LysoPC(10:0/0:0)LysoPC(10:0/0:0) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2 as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines 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. LysoPC(10:0/0:0), in particular, consists of one chain of capric acid at the C-1 position.C04230 PHOSPHATIDYLCHOLINE[H][C@@](O)(COC(=O)CCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)CC18H38NO7PInChI=1S/C18H38NO7P/c1-5-6-7-8-9-10-11-12-18(21)24-15-17(20)16-26-27(22,23)25-14-13-19(2,3)4/h17,20H,5-16H2,1-4H3/t17-/m1/s1SECPDKKEUKDCPG-QGZVFWFLSA-N(2-{[(2R)-3-(decanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium411.476411.238589566-4.801(2-{[(2R)-3-(decanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium00LysoPC(10:0/0:0);LPC(10:0/0:0);GPC(10:0/0:0);Lysophosphatidylcholine(10:0/0:0);1-Decanoyl-sn-glycero-3-phosphocholine;1-Decanoyl-lysophosphatidylcholine;1-Decanoyl-GPC;LysoPC(10:0);LPC(10:0);GPC(10:0);Lysophosphatidylcholine(10:0)PW_C1083271034Adenosine 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_C001034ADP2341348415224821380159631597831061141518219014921041821131021615824085924352727284727364628552931657236356144002344763147709150362651577520897521710053151115349112539210354461205544129557213356241085741117576410158491435856146587810758991475926151605015561111616231166649517867009468411886872160715920571872067208210722621372312117300198730321673912177410218743316374832228187225118512771190517012013281121802851326222315329308423283154239831342622322426963187702925377087132772161347730632977472333776633367803933278043350781701287821535178244353784143357849511578705331788491307892033480030368806221188065113580676119948271241132833881162041091199441221199944061201564071203183821203664121212484291213941231213994331214724081218993831219764101220641251220854051224054221224454351229733991230134461238184641239534471239584681240303741244523981245294441246151361246363761249474721249753751250124701253342971253734791254922991255174811256454841261254851262193001262354951262424781265504911265974991269155011277335161277803951277973901278032091281225081281685171283133891104PhosphateHMDB0001429Phosphate 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_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153897097LysoPE(14:0/0:0)HMDB0011500LysoPE(14:0/0:0) is a lysophosphatidylethanolamine or a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylethanolamines (LPEs) can function as plant growth regulators with several diverse uses. (LPEs) are approved for outdoor agricultural use to accelerate ripening and improve the quality of fresh produce. They are also approved for indoor use to preserve stored crops and commercial cut flowers. As a breakdown product of phosphatidylethanolamine (PE), LPE is present in cells of all organisms.86583448842997826020[H][C@@](O)(COC(=O)CCCCCCCCCCCCC)COP(O)(=O)OCCNC19H40NO7PInChI=1S/C19H40NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(22)25-16-18(21)17-27-28(23,24)26-15-14-20/h18,21H,2-17,20H2,1H3,(H,23,24)/t18-/m1/s1RPXHXZNGZBHSMJ-GOSISDBHSA-N(2-aminoethoxy)[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphinic acid425.4972425.254239151-4.7832-aminoethoxy(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxyphosphinic acid001-myristoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine;Lpe(14:0);Lpe(14:0/0:0);Lyso-pe(14:0);Lyso-pe(14:0/0:0);Lysope(14:0);Lysope(14:0/0:0);Lysophosphatidylethanolamine(14:0);Lysophosphatidylethanolamine(14:0/0:0);Tetradecanoyl-lysophosphatidylethanolamine;1-tetradecanoyl-sn-glycero-3-phosphoethanolamine;1-tetradecanoyl-sn-glycero-3-phosphoethanolamine zwitterion;Lpe (14:0/0:0)PW_C007097LPE14:075061907507188750916359GlycerophosphocholineHMDB0000086Glycerophosphorylcholine (GPC) is a choline derivative and one of the two major forms of choline storage (along with phosphocholine) in the cytosol. Glycerophosphorylcholine is also one of the four major organic osmolytes in renal medullary cells, changing their intracellular osmolyte concentration in parallel with extracellular tonicity during cellular osmoadaptation. As an osmolyte, Glycerophosphorylcholine counteracts the effects of urea on enzymes and other macromolecules. Kidneys (especially medullar cells), which are exposed under normal physiological conditions to widely fluctuating extracellular solute concentrations, respond to hypertonic stress by accumulating the organic osmolytes glycerophosphorylcholine (GPC), betaine, myo-inositol, sorbitol and free amino acids. Increased intracellular contents of these osmolytes are achieved by a combination of increased uptake (myo-inositol and betaine) and synthesis (sorbitol, GPC), decreased degradation (GPC) and reduced osmolyte release. GPC is formed in the breakdown of phosphatidylcholine (PtC). This pathway is active in many body tissues, including mammary tissue.28319-77-9C006707192016870GLYCERYLPHOSPHORYLCHOLINE64931C[N+](C)(C)CCOP([O-])(=O)OC[C@@H](O)COC8H20NO6PInChI=1S/C8H20NO6P/c1-9(2,3)4-5-14-16(12,13)15-7-8(11)6-10/h8,10-11H,4-7H2,1-3H3/t8-/m0/s1SUHOQUVVVLNYQR-QMMMGPOBSA-N(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium257.2213257.102823889-1.542(2-{[(2R)-2,3-dihydroxypropyl phosphono]oxy}ethyl)trimethylazanium00FDB0218022-[[(2,3-dihydroxypropoxy)hydroxyphosphinyl]oxy]-n,n,n-trimethyl-ethanaminium inner salt;Choline alfoscerate;Choline glycerophosphate;Gpc;Gpcho;Glycerol 3-phosphocholine;Glycerol phosphorylcholine;Glycerol-3-phosphatidylcholine;Glycerophosphatidylcholine;Glycerophosphocholine;Glycerophosphorylcholine;Hydrogen glycerophosphate choline;L-choline hydroxide 2,3-dihydroxypropyl hydrogen phosphate inner salt;L-alpha-glycerophosphocholine;L-alpha-glycerophosphorylcholine;L-alpha-glycerylphosphorylcholine;Sn-glycero-3-phosphocholine;A-glycerophosphorylcholine;A-glycerylphosphorylcholine;Alpha-glycerophosphorylcholine;Alpha-glycerylphosphorylcholinePW_C000059GPC32022686832257878713212253912412510011812668929912826838840034Hydrogen 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039581Glycerol 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_C000081Glyc1P104381475214884221155862951076296108841216291221701065318812546151125502231531924934814174246631842467315780301117805235078372345783781327995213481808253938261249478938411055338811063639111584011812075612212129741812134512112141543312335313512386745412397446812578829712597848912599129912724320512743150665CholineHMDB0000097Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer.62-49-7C0011430515354CPD-563299DB00122C[N+](C)(C)CCOC5H14NOInChI=1S/C5H14NO/c1-6(2,3)4-5-7/h7H,4-5H2,1-3H3/q+1OEYIOHPDSNJKLS-UHFFFAOYSA-N(2-hydroxyethyl)trimethylazanium104.1708104.107539075-1.591choline11FDB000710(2-hydroxyethyl)trimethyl ammonium;(2-hydroxyethyl)trimethylammonium;(beta-hydroxyethyl)trimethylammonium;2-hydroxy-n,n,n-trimethyl-ethanaminium;2-hydroxy-n,n,n-trimethylethanaminium;Bilineurine;Biocolina;Biocoline;Choline;Choline cation;Choline ion;Cholinum;Hepacholine;Hormocline;Lipotril;N,n,n-trimethylethanol-ammonium;N,n,n-trimethylethanolammonium;Neocolina;Paresan;N-trimethylethanolamine;TrimethylethanolaminePW_C000065Choline562356415565814971456121195619137684971218515112197164122782261533921538049776141127761911478530115799721327998033194829124948593831132853881155411181157533981204894071204974091213064051238763761259874781264714811274402091280402061202PhosphorylcholineHMDB0001565Phosphorylcholine is a small haptenic molecule, is found in a wide variety of organisms. Human hepatic tumors undergo an elevation in the concentration of phosphorylcholine as the principal metabolic change is observed (PMID: 11076016). Phosphorylcholine is the precursor metabolite of choline in the glycine, serine and threonine metabolism pathways (KEGG, map00260) and in intermediate between choline and cytidine-diphosphate choline in the glycerophospholipid metabolism pathway (KEGG, map00564).107-73-3C00588101418132PHOSPHORYL-CHOLINE989DB03945C[N+](C)(C)CCOP(O)(O)=OC5H15NO4PInChI=1S/C5H14NO4P/c1-6(2,3)4-5-10-11(7,8)9/h4-5H2,1-3H3,(H-,7,8,9)/p+1YHHSONZFOIEMCP-UHFFFAOYSA-O[2-(trimethylazaniumyl)ethoxy]phosphonic acid184.1507184.073869485-1.702ChoP1-1FDB022692Choline phosphate;N-trimethyl-2-aminoethylphosphonate;O-phosphocholine;Phosphocholine;Phosphoryl-choline;Chop;Phosphorylcholine;Trimethyl(2-(phosphonooxy)ethyl)ammonium;Choline phosphoric acid;N-trimethyl-2-aminoethylphosphonic acidPW_C001202CHOP151122167434976872392141218415178534132788753569481312411326938811552611812209241912464345512599729912624949012781150757Cytidine 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_C000057CTP4272311508271825766101580010870771887593160913719591422131219416412510288152851511531724915342221537418347591742650315773151287844811178733132799491347995713079964329804161709478438494812125948173829867722311063339111326839511327338911552513611553039912032841012085412212134012112221212412298344412343413512476411812565448512584029712637429912729220512793538843034CDP-CholineHMDB0001413Citicoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Once absorbed, citicoline is widely distributed throughout the body, crosses the blood-brain barrier and reaches the central nervous system (CNS), where it is incorporated into the membrane and microsomal phospholipid fraction. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Owing to these pharmacological mechanisms, citicoline has a neuroprotective effect in hypoxic and ischemic conditions, decreasing the volume of ischemic lesion, and also improves learning and memory performance in animal models of brain aging. In addition, citicoline has been shown to restore the activity of mitochondrial ATPase and membrane Na+/K+ATPase, to inhibit activation of certain phospholipases, and to accelerate reabsorption of cerebral edema in various experimental models. Citicoline has also been shown to be able to inhibit mechanisms of apoptosis associated to cerebral ischemia and in certain neurodegeneration models, and to potentiate neuroplasticity mechanisms. Citicoline is a safe drug, as shown by the toxicological tests conducted, that has no significant systemic cholinergic effects and is a well tolerated product (PMID: 17171187).987-78-0C003071158397116436CDP-CHOLINE13207C[N+](C)(C)CCOP([O-])(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=OC14H26N4O11P2InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/t9-,11-,12-,13-/m1/s1RZZPDXZPRHQOCG-OJAKKHQRSA-N{2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphono)oxy]ethyl}trimethylazanium488.324488.107330718-1.834[2-({[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphono}oxy)ethyl]trimethylazanium0-1Audes;Cereb;Choline 5'-cytidine diphosphate;Choline cytidine diphosphate;Citicholine;Citicoline;Citidoline;Citifar;Colite;Corenalin;Cyscholin;Cytidine 5'-(choline diphosphate);Cytidine 5'-(cholinyl pyrophosphate);Cytidine 5'-diphosphate choline;Cytidine 5'-diphosphocholine;Cytidine 5-diphosphate-trihydrogen;Cytidine choline diphosphate;Cytidine diphosphate choline;Cytidine diphosphate choline ester;Cytidine diphosphocholine;Cytidine diphosphorylcholine;Cytidine-5' diphosphocholine;Cytidine-5'-pyrophosphate-hydroxycholine;Cytidoline;Difosfocin;Emicholine f;Ensign;Haocolin;Hornbest;Neucolis;Nicholin;Nicolin;Niticolin;P-hydroxide[2-(trimethylammonio)ethyl] ester;Reagin;Recofnan;Recognan;Rexort;Sintoclar;Somazina;Somazine;Suncholin;[2-cytidylate-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium;Cdp-colina;Citicolina;Citicolinum;Citidin difosfato de colina;Cyticholine;Cytidindiphosphocholin;Cytidine 5'-diphosphoric choline;[2-cytidylic acid-o'-phosphonyloxyl]-ethyl-trimethyl-ammonium;Cytidine 5'-(choline diphosphoric acid);Cytidine 5'-(cholinyl pyrophosphoric acid)PW_C043034CDP-C12195164152861511533527995913294815124113271388115528118170PyrophosphateHMDB0000250The 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_C000170Ppi12235463842923735328822212173162049241059281529417514486854503489525210452941015409117542410354331185458120554811155591325584133560613556551085879107623916669781997073188713416372721607312198731821382751518283210118691611200222212041164123152251232324912512288125792261269529015219306153751834760174256131542697318772353297731712877635336784163357892833179153112799501347995813080047372804171708563019478638494814125948193829867822311063439111327039511327538911552713611553239911993412212001712412003240612033041012093640712126142912134112112148638312240742212298544412350211912383146412404439812497737512532429712539529912541047912559748412565648512587648112655249112686920512693538812695050112733720612812450855665PC(10:0/10:0)PC(10:0/10:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(10:0/10:0), in particular, consists of two decanoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.[H][C@@](COC(=O)CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCC28H56NO8PInChI=1S/C28H56NO8P/c1-6-8-10-12-14-16-18-20-27(30)34-24-26(25-36-38(32,33)35-23-22-29(3,4)5)37-28(31)21-19-17-15-13-11-9-7-2/h26H,6-25H2,1-5H3/t26-/m1/s1MLKLDGSYMHFAOC-AREMUKBSSA-N(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium565.729565.374354765-6.400(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium00PW_C055665PC9398163943219543145PE(10:0/10:0)PE(10:0/10:0) 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(10:0/10:0), in particular, consists of two decanoyl 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.C0041616337L-PHOSPHATIDATE[H][C@@](COC(=O)CCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCC25H50NO8PInChI=1S/C25H50NO8P/c1-3-5-7-9-11-13-15-17-24(27)31-21-23(22-33-35(29,30)32-20-19-26)34-25(28)18-16-14-12-10-8-6-4-2/h23H,3-22,26H2,1-2H3,(H,29,30)/t23-/m1/s1KKOSJVWUOHEQKA-HSZRJFAPSA-N(2-aminoethoxy)[(2R)-2,3-bis(decanoyloxy)propoxy]phosphinic acid523.648523.327404572-5.4522-aminoethoxy((2R)-2,3-bis(decanoyloxy)propoxy)phosphinic acid00(2r)-3-2-aminoethoxy(hydroxy)phosphoryloxy-2-decanoyloxypropyl decanoate;1,2-didecanoyl-rac-glycero-3-phosphoethanolamine;Gpetn(10:0/10:0);Gpetn(20:0);Pe(20:0);Phophatidylethanolamine(10:0/10:0);Phophatidylethanolamine(20:0)PW_C043145PE20:093951639429195921S-AdenosylmethionineHMDB0001185S-Adenosylmethionine (CAS: 29908-03-0), also known as SAM or AdoMet, is a physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in the treatment of chronic liver disease (From Merck, 11th ed). S-Adenosylmethionine is a natural substance present in the cells of the body. It plays a crucial biochemical role by donating a one-carbon methyl group in a process called transmethylation. S-Adenosylmethionine, formed from the reaction of L-methionine and adenosine triphosphate catalyzed by the enzyme S-adenosylmethionine synthetase, is the methyl-group donor in the biosynthesis of both DNA and RNA nucleic acids, phospholipids, proteins, epinephrine, melatonin, creatine, and other molecules.485-80-3C000192476216515414S-ADENOSYLMETHIONINE31983DB00118C[S+](CC[C@H](N)C(O)=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2NC15H23N6O5SInChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/p+1/t7-,8+,10+,11+,14+,27?/m0/s1MEFKEPWMEQBLKI-AIRLBKTGSA-O[(3S)-3-amino-3-carboxypropyl]({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl})methylsulfanium399.445399.145063566-2.565SAMe11FDB022473(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine;2-s-adenosyl-l-methionine;5'-deoxyadenosine-5'-l-methionine disulfate ditosylate;Active methionine;Ademetionine;Adenosylmethionine;Adomet;Donamet;L-s-adenosylmethionine;S-(5'-adenosyl)-l-methionine;S-(5'-deoxyadenosin-5'-yl)-l-methionine;S-adenosyl methionine;S-adenosyl-l-methionine disulfate tosylate;S-adenosyl-l-methionine;S-adenosyl-methionine;S-adenosylmethionine;5'-deoxyadenosine-5'-l-methionine disulphate ditosylate;S-adenosyl-l-methionine disulphate tosylate;(3s)-5'-[(3-amino-3-carboxypropyl)methylsulfonio]-5'-deoxyadenosine, inner salt;[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl][(3s)-3-amino-3-carboxypropyl](methyl)sulfonium;Acylcarnitine;Sam;SamePW_C000921SAMe51986333070420122031880272066246811050235056041357136163754021075442137632160826615192351951187419812031222123582251529324915345181536330976897293768991647698422477488111777313387777234178099132783033517833534679155112799613618086122948303829483338611328638911328839711554339911554640112039312212053741312093940712105212412228243512317144912350511912361611812483647012585929712587948112630429912644749912732120512734020612759538812801751757424PE-NMe(10:0/10:0)PE-NMe(10:0/10:0) is a monomethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Monomethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PE-NMe(10:0/10:0), in particular, consists of two decanoyl chain at positions C-1 and C2. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.C01241 15958CPD-405[H]C(COC(=O)CCCCCCCCC)(COP(O)(=O)OCCNC)OC(=O)CCCCCCCCCC26H52NO8PInChI=1S/C26H52NO8P/c1-4-6-8-10-12-14-16-18-25(28)32-22-24(23-34-36(30,31)33-21-20-27-3)35-26(29)19-17-15-13-11-9-7-5-2/h24,27H,4-23H2,1-3H3,(H,30,31)GYIZLKMDSNERBX-UHFFFAOYSA-N[2,3-bis(decanoyloxy)propoxy][2-(methylamino)ethoxy]phosphinic acid537.675537.343054636-5.8222,3-bis(decanoyloxy)propoxy(2-(methylamino)ethoxy)phosphinic acid00MMPE;monomethylphosphatidylethanolamine;N-monomethylphosphatidylethanolamine;phosphatidyl-N-methylethanolaminePW_C057424MMPE928921393961639430195749S-AdenosylhomocysteineHMDB0000939S-Adenosyl-L-homocysteine (SAH) is formed by the demethylation of S-adenosyl-L-methionine. S-Adenosylhomocysteine (AdoHcy or SAH) is also the immediate precursor of all of the homocysteine produced in the body. The reaction is catalyzed by S-adenosylhomocysteine hydrolase and is reversible with the equilibrium favoring formation of SAH. In vivo, the reaction is driven in the direction of homocysteine formation by the action of the enzyme adenosine deaminase which converts the second product of the S-adenosylhomocysteine hydrolase reaction, adenosine, to inosine. Except for methyl transfer from betaine and from methylcobalamin in the methionine synthase reaction, SAH is the product of all methylation reactions that involve S-adenosylmethionine (SAM) as the methyl donor. Methylation is significant in epigenetic regulation of protein expression via DNA and histone methylation. The inhibition of these SAM-mediated processes by SAH is a proven mechanism for metabolic alteration. Because the conversion of SAH to homocysteine is reversible, with the equilibrium favoring the formation of SAH, increases in plasma homocysteine are accompanied by an elevation of SAH in most cases. Disturbances in the transmethylation pathway indicated by abnormal SAH, SAM, or their ratio have been reported in many neurodegenerative diseases, such as dementia, depression, and Parkinson's disease (PMID: 18065573, 17892439). Therefore, when present in sufficiently high levels, S-adenosylhomocysteine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of S-adenosylhomocysteine are associated with S-adenosylhomocysteine (SAH) hydrolase deficiency and adenosine deaminase deficiency. S-Adenosylhomocysteine forms when there are elevated levels of homocysteine and adenosine. S-Adenosyl-L-homocysteine is a potent inhibitor of S-adenosyl-L-methionine-dependent methylation reactions. It is toxic to immature lymphocytes and can lead to immunosuppression (PMID: 221926).979-92-0C000212524622216680ADENOSYL-HOMO-CYS388301N[C@@H](CCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C1N=CN=C2N)C(O)=OC14H20N6O5SInChI=1S/C14H20N6O5S/c15-6(14(23)24)1-2-26-3-7-9(21)10(22)13(25-7)20-5-19-8-11(16)17-4-18-12(8)20/h4-7,9-10,13,21-22H,1-3,15H2,(H,23,24)(H2,16,17,18)/t6-,7+,9+,10+,13+/m0/s1ZJUKTBDSGOFHSH-WFMPWKQPSA-N(2S)-2-amino-4-({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}sulfanyl)butanoic acid384.411384.12158847-1.975S-adenosyl-L-homocysteine00DBMET00514FDB022327(s)-5'-(s)-(3-amino-3-carboxypropyl)-5'-thioadenosine;2-s-adenosyl-l-homocysteine;5'-deoxy-s-adenosyl-l-homocysteine;5'-s-(3-amino-3-carboxypropyl)-5'-thio-l-adenosine;Adenosyl-l-homocysteine;Adenosyl-homo-cys;Adenosylhomo-cys;Adenosylhomocysteine;Adohcy;Formycinylhomocysteine;L-5'-s-(3-amino-3-carboxypropyl)-5'-thior-adenosine;L-s-adenosyl-homocysteine;L-s-adenosylhomocysteine;S-(5'-adenosyl)-l-homocysteine;S-(5'-deoxyadenosin-5'-yl)-l-homocysteine;S-(5'-deoxyadenosine-5')-l-homocysteine;S-adenosyl-l-homocysteine;S-adenosyl-homocysteine;Sah;(2s)-2-amino-4-({[(2s,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl}sulfanyl)butanoic acid;S-[1-(adenin-9-yl)-1,5-dideoxy-beta-d-ribofuranos-5-yl]-l-homocysteine;S-adenosylhomocysteinePW_C000749SAH520857518635307052012213188227206724683105025505607136713716375422107546213763416082681519237195118751981235922515294249153643097748911177611130777333387777334178098132783053517833734679156112799623618086322948313829483438611328738911328939711554439911554740112039412212048612512053941312094040712105312412228443512303713512317344912350611912361711812483847012588048112630329912644949912734120612759638812801951757582PE-NMe2(10:0/10:0)PE-NMe2(10:0/10:0) is a dimethylphosphatidylethanolamine. It is a glycerophospholipid, and is formed by sequential methylation of phosphatidylethanolamine as part of a mechanism for biosynthesis of phosphatidylcholine. Dimethylphosphatidylethanolamines are usually found at trace levels in animal or plant tissues. They can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions.PE-NMe2(10:0/10:0), in particular, consists of two decanoyl chain at positions C-1 and C2. Fatty acids containing 16, 18 and 20 carbons are the most common. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.C0430852332CPD-160[H]C(COC(=O)CCCCCCCCC)(COP(O)(=O)OCCN(C)C)OC(=O)CCCCCCCCCC27H54NO8PInChI=1S/C27H54NO8P/c1-5-7-9-11-13-15-17-19-26(29)33-23-25(24-35-37(31,32)34-22-21-28(3)4)36-27(30)20-18-16-14-12-10-8-6-2/h25H,5-24H2,1-4H3,(H,31,32)TYNWDCXXGCGOJR-UHFFFAOYSA-N[2,3-bis(decanoyloxy)propoxy][2-(dimethylamino)ethoxy]phosphinic acid551.702551.358704701-5.5112,3-bis(decanoyloxy)propoxy(2-(dimethylamino)ethoxy)phosphinic acid00dimethylphosphatidylethanolamine;DMPE;N-dimethylphosphatidylethanolamine ;phosphatidyl-N-dimethylethanolamine;phosphatidyl-N,N-dimethylethanolaminePW_C057582DMPE92902139397163943119545274Lyso-PS(14:0/0:0)Lyso-PS(14:0/0:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PS(14:0/0:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylserines (LPSs) enhance glucose transport, lowering blood glucose levels while leaving secretion of insulin unaffected. LPSs have been known as a signaling phospholipid in mast cell biology. They enhance stimulated histamine release and eicosanoid production. LPSs also play a roles in the promotion of phagocytosis of apoptotic cells and resolution of inflammation.CCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC([NH3+])C([O-])=OC20H39NO9PInChI=1S/C20H40NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(23)28-14-17(22)15-29-31(26,27)30-16-18(21)20(24)25/h17-18,22H,2-16,21H2,1H3,(H,24,25)(H,26,27)/p-1ZJMQYSXCPARLHG-UHFFFAOYSA-M2-azaniumyl-3-{[2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}propanoate468.504468.236792418-4.9722-ammonio-3-{[2-hydroxy-3-(tetradecanoyloxy)propyl phosphono]oxy}propanoate-1-1PW_C045274LPS14:0910218891031607860PS(14:0/14:0)HMDB0012330PS(14:0/14:0) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PS(14:0/14:0), in particular, consists of two tetradecanoyl chains at positions C-1 and C-2. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.C0273712369918303L-1-PHOSPHATIDYL-SERINE110272DB00144[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)C(O)=OC34H66NO10PInChI=1S/C34H66NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-32(36)42-27-30(28-43-46(40,41)44-29-31(35)34(38)39)45-33(37)26-24-22-20-18-16-14-12-10-8-6-4-2/h30-31H,3-29,35H2,1-2H3,(H,38,39)(H,40,41)/t30-,31+/m1/s1WKJDWDLHIOUPPL-JSOSNVBQSA-N(2S)-2-amino-3-({[(2R)-2,3-bis(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid679.873679.442434327-6.503dimyristoyl phosphatidylserine0-11-myristoyl-2-myristoyl-sn-glycero-3-phosphoserine;Ps(14:0/14:0);Ps(28:0);Pser(14:0/14:0);Pser(28:0);Phosphatidylserine(14:0/14:0);Phosphatidylserine(28:0)PW_C007860PS1491041959120163153983092210649221071725477249893311349376333110511638411037338311604412112767639845275Lyso-PI(14:0/0:0)Lyso-PI(14:0/0:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PI(14:0/0:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylinositol is an endogenous lysophospholipid and endocannabinoid neurotransmitter.CCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OC1C(O)C(O)C(O)C(O)C1OC23H45O12PInChI=1S/C23H45O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(25)33-14-16(24)15-34-36(31,32)35-23-21(29)19(27)18(26)20(28)22(23)30/h16,18-24,26-30H,2-15H2,1H3,(H,31,32)FEWCZOSQEKFJGK-UHFFFAOYSA-N[2-hydroxy-3-(tetradecanoyloxy)propoxy][(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid544.575544.264863887-2.7872-hydroxy-3-(tetradecanoyloxy)propoxy((2,3,4,5,6-pentahydroxycyclohexyl)oxy)phosphinic acid0-1PW_C045275LPI14:09106190910718845276PI(14:0/14:0)PI(14:0/14:0)is a phosphatidylinositol. Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols 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 18 and 20 carbons are the most common.PI(14:0/14:0), in particular, consists of two tetradecanoyl chains at positions C-1 and C-2 to the C-2 atom. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. 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. PIs contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCCCCCCCCC37H71O13PInChI=1S/C37H71O13P/c1-3-5-7-9-11-13-15-17-19-21-23-25-30(38)47-27-29(49-31(39)26-24-22-20-18-16-14-12-10-8-6-4-2)28-48-51(45,46)50-37-35(43)33(41)32(40)34(42)36(37)44/h29,32-37,40-44H,3-28H2,1-2H3,(H,45,46)/t29-,32?,33-,34?,35?,36?,37-/m1/s1LYBDVVBIMGTZMB-JJBQLUTRSA-N[(2R)-2,3-bis(tetradecanoyloxy)propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid754.9256754.46322887-5.216(2R)-2,3-bis(tetradecanoyloxy)propoxy[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid0-1PW_C045276Pl14910819545277Lyso-PS(0:0/14:0)Lyso-PS(0:0/14:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PS(0:0/14:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylserines (LPSs) enhance glucose transport, lowering blood glucose levels while leaving secretion of insulin unaffected. LPSs have been known as a signaling phospholipid in mast cell biology. They enhance stimulated histamine release and eicosanoid production. LPSs also play a roles in the promotion of phagocytosis of apoptotic cells and resolution of inflammation.CCCCCCCCCCCCCC(=O)OC(CO)COP([O-])(=O)OCC([NH3+])C([O-])=OC20H39NO9PInChI=1S/C20H40NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(23)30-17(14-22)15-28-31(26,27)29-16-18(21)20(24)25/h17-18,22H,2-16,21H2,1H3,(H,24,25)(H,26,27)/p-1TZPRMIGZGQOWBD-UHFFFAOYSA-M2-azaniumyl-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate468.504468.236792418-4.9522-ammonio-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate-1-1PW_C045277LPS0:149109190911018845278Lyso-PI(0:0/14:0)Lyso-PI(0:0/14:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PI(0:0/14:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylinositol is an endogenous lysophospholipid and endocannabinoid neurotransmitter.CCCCCCCCCCCCCC(=O)OC(CO)COP(O)(=O)OC1C(O)C(O)C(O)C(O)C1OC23H45O12PInChI=1S/C23H45O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(25)34-16(14-24)15-33-36(31,32)35-23-21(29)19(27)18(26)20(28)22(23)30/h16,18-24,26-30H,2-15H2,1H3,(H,31,32)KJKJVATVGMLDCK-UHFFFAOYSA-N[3-hydroxy-2-(tetradecanoyloxy)propoxy][(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid544.575544.264863887-2.6973-hydroxy-2-(tetradecanoyloxy)propoxy((2,3,4,5,6-pentahydroxycyclohexyl)oxy)phosphinic acid0-1PW_C045278LPI0:149111190911218843337DG(10:0/10:0/0:0)DG(10:0/10:0/0:0) 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(10:0/10:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.C00165DIACYLGLYCEROL[H][C@@](CO)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCC23H44O5InChI=1S/C23H44O5/c1-3-5-7-9-11-13-15-17-22(25)27-20-21(19-24)28-23(26)18-16-14-12-10-8-6-4-2/h21,24H,3-20H2,1-2H3/t21-/m1/s1GNSDEDOVXZDMKM-OAQYLSRUSA-N(2R)-1-(decanoyloxy)-3-hydroxypropan-2-yl decanoate400.6400.318874517-5.811(R)-1,2-didecanoylglycerol00(2-decanoyloxy-3-hydroxypropyl) decanoate;1,2-dicaprin;1,2-didecanoyl-rac-glycerol;3-hydroxypropane-1,2-diyl didecanoate;Dag(10:0/10:0);Dag(20:0);Dg(10:0/10:0);Dg(20:0);Diacylglycerol;Diacylglycerol(10:0/10:0);Diacylglycerol(20:0);DiglyceridePW_C043337DG20:092911951065816010660170255014964Cytidine 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_C000064CMP1151825121427342338618497256576810158021087079188759516091472499151224925719512196164122101511527428515336308153734934815174265231578449111784881157857313078736132799531347996933180421170947913849482138398680223110637391113277390115535398120855122121346121122216124122487405122605125123435135124768118125053376125177136125841297126378299126641478126752300127293205127940388128217209128346395271a carboxylateCompound642CompoundPW_EC000271AC11104Probable phospholipid-transporting ATPase DNF3Q12674
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids.
DNF3293.6.3.1751021111105Probable phospholipid-transporting ATPase DNF3Q12674
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids.
DNF3293.6.3.1751121111106Uncharacterized protein YNR048WP53740YNR048W29751221110959Lysophospholipase NTE1Q04958
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium.
NTE1293.1.1.57742210786216010960Glycerophosphodiester phosphodiesterase GDE1Q02979
Glycerophosphocholine glycerophosphodiesterase responsible for the hydrolysis of intracellular glycerophosphocholine into glycerol-phosphate and choline. The choline is used for phosphatidyl-choline synthesis. Required for utilization of glycerophosphocholine as phosphate source.
GDE1293.1.4.46774316010957Choline kinaseP20485
Responsible for phosphatidylcholine synthesis via the CDP-choline pathway. Also exhibits ethanolamine kinase activity but at 14% efficiency compared with choline.
CKI1292.7.1.32774416010956Choline-phosphate cytidylyltransferaseP13259PCT1292.7.7.15774516011103Ale1p acyltransferaseA0A0D4EFH3ALE145786121391051959114162912116311298Phosphatidylethanolamine N-methyltransferaseP05374Catalyzes the first step in the conversion of phosphatidylethanolamine to phosphatidylcholine during the methylation pathway of phosphatidylcholine biosynthesis.CHO2292.1.1.1790992139117163923819511299Phosphatidyl-N-methylethanolamine N-methyltransferaseP05375Catalyzes three sequential methylation reactions of phosphatidylethanolamine (PE) by AdoMet, thereby producing phosphatidylcholine (PC).OPI3292.1.1.17; 2.1.1.7191012139119163924019511100Phospholipid-transporting ATPase DNF1P32660
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids.
DNF1293.6.3.1750321111101Phospholipid-transporting ATPase DNF2Q12675
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids. Required for protein transport from Golgi to vacuoles.
DNF2293.6.3.1750421111102Alkylphosphocholine resistance protein LEM3P42838
Involved in the asymmetrical organization of phosphatidylethanolamine in the plasma membrane.
LEM329750521110940diacylglycerol cholinephosphotransferaseP17898
Catalyzes the final step in the CDP-choline route leading to phosphatidylcholin (PC). Preferentially uses CDP-monomethylethanolamine as aminoalcohol substrate. Shows highest activity toward di- and mono-unsaturated diacylglycerol species as lipid substrates. The CDP-choline pathway only contributes to net PC synthesis if exogenous choline is present. In its absence, this pathway recycles choline from PC turnover and may contribute to maintaining the proper PC species composition.
CPT1292.7.8.277412107757160786321392581954881Phospholipid-transporting ATPase 18PW_P0048811212311100121241110112125111024727Lysophospholipase NTE118PW_P00472711910109594728Glycerophosphodiester phosphodiesterase GDE118PW_P00472811911109604729Choline kinase18PW_P00472911912109574730Choline-phosphate cytidylyltransferase18PW_P00473011913109564882Ale1p acyltransferase18PW_P00488212126111035031Phosphatidylethanolamine N-methyltransferase18PW_P00503112322112985032Phosphatidyl-N-methylethanolamine N-methyltransferase18PW_P00503212323112994716diacylglycerol cholinephosphotransferase18PW_P0047161189810940188266falsePW_R188266Right7136011083271Compoundfalse71360214201Compoundfalse713603591Compoundfalse7136042711ElementCollectionfalse17791347273.1.1.56999falsePW_R006999Right28835591Compoundfalse2883614201Compoundfalse28837400341Compoundfalse28838811Compoundfalse28839651Compoundfalse697747283.1.4.467000falsePW_R007000Right28840651Compoundfalse288414141Compoundfalse2884210341Compoundfalse28843400341Compoundfalse2884412021Compoundfalse697847292.7.1.327001falsePW_R007001Right2884512021Compoundfalse28846571Compoundfalse28847400341Compoundfalse28848430341Compoundfalse288491701Compoundfalse697947302.7.7.15188267falsePW_R188267Right7136051083271Compoundfalse713606556651Compoundfalse17791448827537falsePW_R007537Right31200431451Compoundfalse312019211Compoundfalse31202574241Compoundfalse31203400341Compoundfalse312047491Compoundfalse753650312.1.1.177538falsePW_R007538Right31205574241Compoundfalse312069211Compoundfalse31207575821Compoundfalse312087491Compoundfalse31209400341Compoundfalse753750322.1.1.17,2.1.1.717539falsePW_R007539Right31210575821Compoundfalse312119211Compoundfalse312127491Compoundfalse31213400341Compoundfalse31214556651Compoundfalse753850327540falsePW_R007540Right31215430341Compoundfalse31216433371Compoundfalse31217641Compoundfalse31218400341Compoundfalse31219556651Compoundfalse75394716462PW_RCT000462Right2553462414Compound119025544621420Compound11902555462108327Compound119025564621034Compound118825574621104Compound11882558462108327Compound1188462207PW_RCT000207Right1233207414Compound119012342071420Compound119012352077097Compound119012362071034Compound118812372071104Compound118812382077097Compound1188207208PW_RCT000208Right1239208414Compound119012402081420Compound1160124120845274Compound118812422081034Compound116012432081104Compound1160124420845274Compound1160208209PW_RCT000209Right124520945274Compound216012462097860Compound1195209210PW_RCT000210Right124721045275Compound11901248210414Compound118812492101420Compound1188125021045275Compound118812512101034Compound118812522101104Compound1188210211PW_RCT000211Right125321145275Compound1188125421145276Compound1195211212PW_RCT000212Right125521245277Compound11901256212414Compound118812572121420Compound1188125821245277Compound118812592121034Compound118812602121104Compound1188212213PW_RCT000213Right126121345277Compound118812622137860Compound1195213214PW_RCT000214Right1263214414Compound118812642141420Compound1188126521445278Compound119012662141034Compound118812672141104Compound1188126821445278Compound1188214215PW_RCT000215Right126921545278Compound1188127021545276Compound1195215463PW_RCT000463Right25594637097Compound1188256046343145Compound1163463277017941419042false59541610regular5030277018041419042false3365117110regular5030277018141442false276112610regular5030277018241419042false149539410regular5030277018341418842false1271207910regular5030277018441418842false2142208110regular5030277018641418842false243939510regular50302770187142019049false68539210regular78782770188142019049false3350105710regular78782770189142049false77258610regular78782770190142049false24363210regular78782770191142016049false137538010regular78782770193142018849false1166205510regular78782770194142018849false2037205710regular78782770196142018849false233438110regular787827701971083271903false92310110regular10010027701991083271883false92149110regular1001002770200103418843false126242110regular50302770201103418843false3372143110regular50302770202103443false272132110regular50302770203103416043false200738410regular50302770204103418843false1699208410regular50302770205103418843false2610208610regular50302770206103418843false295139010regular50302770207110418846false117741910regular44432770208110418846false3402149410regular44432770209110416046false209238710regular44432770210110418846false1799207710regular44432770211110418846false2695207910regular44432770212110418846false303139310regular4443277021770971903false3633125110regular100100277021870971883false3161125110regular1001002770221593false31649110regular10010027702234003455false23382710regular787827702244003455false412131710regular787827702254003455false412160710regular787827702264003421355false2127117910regular787827702274003421355false1586118010regular787827702284003421355false1057117810regular787827702304003419555false802204310regular78782770231813false43181610regular1001102770232653false31697610regular100100277023512023false315144610regular1001002770239573false227158110regular1001102770241430343false315194610regular100100277024217045false250181410regular63432770243556653false921124610regular1001002770247431453false2506125110regular10010027702489212133false2381115110regular10011027702499212133false1846114910regular10011027702509212133false1341135910regular1001102770251574242133false1971124410regular10011027702527492133false2096134710regular10011027702547492133false1586134410regular10011027702557492133false1041135810regular1001102770258575822133false1451124410regular1001102770260452741883false17339410regular100110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