81PathwayPhospholipid BiosynthesisThis pathway describes the synthesis of the common phospholipids, including phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol and cardiolipins. Phospholipid synthesis is mediated by two possible mechanisms: (1) A CDP-activated polar head group for attaches to the phosphate of phosphatidic acid or (2) A CDP-activated 1,2-diacylglycerol and an inactivated polar head group. The ER membrane is the primary site of phospholipid synthesis using precursors imported into the ER from the cytosol. To initiate the process, phosphatidic acid is generated by the linkage of two fatty acids associated with coenzyme A (CoA) carriers to glycerol-3-phosphate. This new molecule is inserted into the membrane where a phosphatase converts it into diacylglycerol or alternatively it is formed into phosphatidylinositol before the conversion. If the conversion into diacylglycerol occurs, the molecule has three possible fates depending on the type of polar head group attached: phosphatidylcholine, phosphatidylethanolamine, or phosphatidylserine.
At their inception, a phospholipid is composed of a saturated fatty acid and unsaturated fatty acid on the C1 and C2 carbon of the glycerol backbone respectively. With the continuous remodelling of the phospholipid bilayer, this fatty acid distribution at these carbons changes. For example, acyl group remodelling changes the presence of acyl groups on the glycerol backbone (which were initially placed there by acyl transferases) and moves it further into the membrane as a consequence of the action of phospholipase A1 (PLA1) and phospholipase A2 (PLA2). Another modifying group that is usually added are alcohol-containing groups such as serine, ethanol amine, and choline which contain positively-charged nitrogen.MetabolicPW000048CenterPathwayVisualizationContext4847004000#000099PathwayVisualization5881Phospholipid BiosynthesisThis pathway describes the synthesis of the common phospholipids, including phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol and cardiolipins. Phospholipid synthesis is mediated by two possible mechanisms: (1) A CDP-activated polar head group for attaches to the phosphate of phosphatidic acid or (2) A CDP-activated 1,2-diacylglycerol and an inactivated polar head group. The ER membrane is the primary site of phospholipid synthesis using precursors imported into the ER from the cytosol. To initiate the process, phosphatidic acid is generated by the linkage of two fatty acids associated with coenzyme A (CoA) carriers to glycerol-3-phosphate. This new molecule is inserted into the membrane where a phosphatase converts it into diacylglycerol or alternatively it is formed into phosphatidylinositol before the conversion. If the conversion into diacylglycerol occurs, the molecule has three possible fates depending on the type of polar head group attached: phosphatidylcholine, phosphatidylethanolamine, or phosphatidylserine.
At their inception, a phospholipid is composed of a saturated fatty acid and unsaturated fatty acid on the C1 and C2 carbon of the glycerol backbone respectively. With the continuous remodelling of the phospholipid bilayer, this fatty acid distribution at these carbons changes. For example, acyl group remodelling changes the presence of acyl groups on the glycerol backbone (which were initially placed there by acyl transferases) and moves it further into the membrane as a consequence of the action of phospholipase A1 (PLA1) and phospholipase A2 (PLA2). Another modifying group that is usually added are alcohol-containing groups such as serine, ethanol amine, and choline which contain positively-charged nitrogen.Metabolic18783SubPathway15681Compound1811847764590SubPathway1203755826Compound93166Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.81Pathway67Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.81Pathway68Vance, D.E., and Vance, J.E. Biochemistry of lipids, lipoproteins, and membranes (4th ed.) (2002) Amsterdam; Boston: Elsevier.81Pathway27963418952570Fagone P, Jackowski S: Membrane phospholipid synthesis and endoplasmic reticulum function. J Lipid Res. 2009 Apr;50 Suppl:S311-6. doi: 10.1194/jlr.R800049-JLR200. Epub 2008 Oct 23.81Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404CardiomyocyteCL:00007468Beta cellCL:00006396MyocyteCL:00001871Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly21Xenopus laevis8355EukaryoteAfrican clawed frog49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria51Picea sitchensis3332EukaryoteSitka spruce19Schizosaccharomyces pombe4896Eukaryote196Homo1924EukaryoteHuman15Plasmodium falciparum5833Eukaryote5CytoplasmGO:00057371CytosolGO:00058294PeroxisomeGO:000577724Mitochondrial Intermembrane SpaceGO:000575814Mitochondrial Outer MembraneGO:000574131Periplasmic SpaceGO:000562012Mitochondrial Inner MembraneGO:000574313Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588632Inner MembraneGO:00702582MitochondrionGO:00057393Mitochondrial MatrixGO:000575925Golgi ApparatusGO:000579427Peroxisome MembraneGO:000577815NucleusGO:000563426Golgi Apparatus MembraneGO:000013935ChloroplastGO:000950711Extracellular SpaceGO:00056156LysosomeGO:000576416Lysosomal LumenGO:004320220Endoplasmic Reticulum LumenGO:000578834Plant-Type VacuoleGO:000032539Mitochondrial membraneGO:003196619Sarcoplasmic ReticulumGO:001652936MembraneGO:00160208Smooth Endoplasmic Reticulum GO:000579021SynapseGO:00452021LiverBTO:00007597292Endothelium BTO:00003937Nervous SystemBTO:00014845cardiocyteBTO:00015398Blood VesselBTO:0001102741118PancreasBTO:00009886KidneyBTO:00006717189MuscleBTO:0000887141183Sympathetic Nervous SystemBTO:000183224BrainBTO:0000142891625IntestineBTO:00006488511PW_BS0000082111PW_BS0000025411PW_BS000005422411PW_BS00004210813PW_BS0001081471241PW_BS000147151141PW_BS0001511601181PW_BS000160315123PW_BS0000241321121PW_BS0001321115121PW_BS00011134524121PW_BS0000283344121PW_BS000028124151PW_BS000124388161PW_BS0001121181171PW_BS000118122551PW_BS0001224182451PW_BS000115408451PW_BS0001151355171PW_BS00013545424171PW_BS0001153744171PW_BS0000532975101PW_BS0000242991101PW_BS00002448924101PW_BS0001154824101PW_BS000115205561PW_BS0000245062461PW_BS000115502461PW_BS0001155811411PW_BS000058107313PW_BS00010716212181PW_BS00016217018PW_BS000170188118PW_BS0000242231241PW_BS0000242491341PW_BS000024171211PW_BS0000173183123PW_BS000024350114121PW_BS00002813412121PW_BS000134253541PW_BS0000243841251PW_BS0001003911261PW_BS00011212112171PW_BS00012143311451PW_BS000115468114171PW_BS00011549711PW_BS000049101711PW_BS000010221411PW_BS00002233217121PW_BS0000283317121PW_BS00002832914121PW_BS0000283821451PW_BS000100383751PW_BS0001002881441PW_BS0000243891461PW_BS000112390761PW_BS00011239914171PW_BS0001133987171PW_BS0001131231751PW_BS00012344717171PW_BS0001154957101PW_BS00011514101PW_BS0000141971418PW_BS0000241893218PW_BS0000241951318PW_BS0000241151012PW_BS000115405105PW_BS0001153761017PW_BS0000534781010PW_BS000115209106PW_BS0000243211PW_BS0000031122121PW_BS000112407251PW_BS0001151192171PW_BS0001194812101PW_BS000115206261PW_BS0000244311PW_BS00000416212PW_BS000016261115PW_BS000026181311PW_BS000018397113PW_BS000039215114PW_BS00002146114PW_BS000046432511PW_BS000043592711PW_BS000059231511PW_BS00002329111PW_BS000029711PW_BS000007311511PW_BS000031918511PW_BS000091541315PW_BS000054562611PW_BS0000561041431PW_BS000104103331PW_BS0001031553241PW_BS0001551613181PW_BS00016116611PW_BS0001661783211PW_BS0001781644PW_BS00016419914181PW_BS0000242137181PW_BS0000242111018PW_BS00002421425181PW_BS0000242164181PW_BS0000241985181PW_BS000024222341PW_BS00002421013181PW_BS0000242253541PW_BS000024226441PW_BS0000242905491PW_BS0000242851041PW_BS0000243081011PW_BS0000241333121PW_BS0001333361121PW_BS00002833527121PW_BS00002835625121PW_BS00002813013121PW_BS0001303683601PW_BS000028184121PW_BS000024372102PW_BS00002815111PW_BS0000155181PW_BS00005127151PW_BS000027406351PW_BS000115429151PW_BS0001154192551PW_BS0001151251351PW_BS0001254222751PW_BS0001151203171PW_BS0001204641171PW_BS00011545525171PW_BS00011513613171PW_BS00013637527171PW_BS00005348414101PW_BS0001154793101PW_BS00011549025101PW_BS00011549127101PW_BS00011530013101PW_BS000024501361PW_BS0001155072561PW_BS0001155082761PW_BS0001153951361PW_BS0001138911421PW_BS00055230635511PW_BS0000242941141PW_BS00002429341PW_BS0000249611PW_BS0000092811611PW_BS0000283612011PW_BS00003613121PW_BS0000136131PW_BS0000061021231PW_BS000102126651PW_BS00012612711651PW_BS00012715612241PW_BS00015611PW_BS00000117912211PW_BS0001791632181PW_BS000163224241PW_BS0000242156181PW_BS0000242273441PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS0000241136121PW_BS000113337116121PW_BS0000283583912PW_BS00002836912601PW_BS0000284436171PW_BS000115448116171PW_BS00011548012101PW_BS000115207661PW_BS000024185321PW_BS0000241861221PW_BS0000243551914PW_BS000035471914PW_BS000047711113PW_BS00007172513PW_BS0000726618518PW_BS000066101531PW_BS0001011901118PW_BS0000241141112PW_BS0001147413PW_BS000074228361PW_BS000024409115PW_BS0001151371117PW_BS0001377906111PW_BS0005248346111PW_BS000549509516PW_BS0000503093911PW_BS00002436139121PW_BS0000283863951PW_BS00010040139171PW_BS000113231391PW_BS000024951721PW_BS000095100521PW_BS00010014117191PW_BS000141117131PW_BS00011729817101PW_BS0000243221231PW_BS00002434713125PW_BS000028943PW_BS0000944251355PW_BS00011546013175PW_BS0001151572241PW_BS0001573331212PW_BS000028111811PW_BS00001175624181PW_BS000516100811961PW_BS000577128524151PW_BS0005883772113PW_BS000037105931113PW_BS000578950242113PW_BS00056348113PW_BS00004878924113PW_BS00052410603113PW_BS000578801111PW_BS00008060251PW_BS000060818512PW_BS00054875718181PW_BS00051621217181PW_BS00002412841151PW_BS0005889312011PW_BS0005591134Dihydroxyacetone phosphateHMDB0001473Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.57-04-5C0011166816108DIHYDROXY-ACETONE-PHOSPHATE648DB04326OCC(=O)COP(O)(O)=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)GNGACRATGGDKBX-UHFFFAOYSA-N170.0578169.998024468FDB0016181,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acidPW_C001134Dhapp102681474233055425342581310859081475936151688416042660315770981327793411178374345785593349382412411055138811583911812073312212256441812259040812333313512513745412516237412578729712595029912671248912673648212724220512830350612833050281Glycerol 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-N172.0737172.013674532FDB0218001-(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_C000081Glyc1P10438147521488422115586295107629610884121629122170106531881254615112550223153192493481417424663184246731578030111780523507837234578378132799521348180825393826124947893841105533881106363911158401181207561221212974181213451211214154331233531351238674541239744681257882971259784891259912991272432051274315063904LysoPA(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-N410.4825410.243340114FDB0250461-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_C003904LPA16:0147749149342208610213458912517015323249254922278046332780553507851933178527345818113299385438293855383108547288110593389110594390115920399115921398121302418121405123121419433123872454123964447123978468125969495125983489127436506531PA(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-N648.903648.47300618FDB0221751,2-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_C000531PA32:01480491494421535142107102140586912197691318991301889138195152981511532524936244223624617780383327804235078520331785283457853711585376329853771349385738394782382947853841085492881085502231105963901106983891106993911159233981213034181213214051213931231213984331216623991216641211238734541238913761239524471239574681259704951259844891260024781274375061274532093019CDP-DG(16:0/16:0)HMDB0006968CDP-DG(16:0/16:0) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. 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. CDP-DG(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(16:0/16:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.C002692477956717962CDPDIACYLGLYCEROL24765809[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCCC44H81N3O15P2InChI=1S/C44H81N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h31-32,36-37,41-43,50-51H,3-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/t36-,37-,41+,42?,43-/m1/s1ITYHVANGBZMQML-QDFYKRCGSA-N954.086953.514292916FDB0241621,2-dihexadecanoyl-rac-glycero-3-cdp;1,2-dipalmitoyl-rac-glycero-3-cytidine-5'-diphosphate;Cdp-dg(16:0/16:0);Cdp-dg(32:0);Cdp-diacylglycerol(16:0/16:0);Cdp-diacylglycerol(32:0)PW_C003019CDPDG1614824915793841516291452493752417785213317854711287449134101211384108598223110888391121292383121348407123862398123911119125972495126023481127426390127475206423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-N24.30523.985041898FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+868227426816476272726811581918883229363998339922111674614834915294317641421241024115929422331262933737454031477491486954497456525310453291115356112537610359061475934151603815560941616250166648417865941646881160697919971702057194206722721372332117250214731021673131987473222117631321184321012312225123242491251328812581226127292901527528515337308771371337723632977937336783933347841733578489115785223317853635678574130800203688004518480048372806231188065413580865158096525381841519383238394900271085962231105593901156873981199744061200701221202473821207024071209814081211811241212654291213194191219241251220864051224084221227591201229213991233071191235463741238354641238894551244771361246373761249783751254472971255984841256694791257774811259214821259472991259734951260004901262434781265534911267533001271253891271645011273805021274073881274515071278042091281255081283473951407738915826PI(16:0/16:0)HMDB0009778PI(16:0/16:0)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(16:0/16:0), in particular, consists of two hexadecanoyl 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.C00626Phosphatidylinositols24767663[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1C(O)C(O)C(O)[C@@H](O)C1O)OC(=O)CCCCCCCCCCCCCCCC41H79O13PInChI=1S/C41H79O13P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(42)51-31-33(32-52-55(49,50)54-41-39(47)37(45)36(44)38(46)40(41)48)53-35(43)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36-41,44-48H,3-32H2,1-2H3,(H,49,50)/t33-,36?,37-,38?,39?,40?,41-/m1/s1IBUKXRINTKQBRQ-NBURIUCMSA-N811.0319810.525829126C006261,2-dihexadecanoyl-rac-glycero-3-phospho-(1'-myo-inositol);1,2-dipalmitoyl-rac-glycero-3-phosphoinositol;Pi(16:0/16:0);Pi(32:0);Pino(16:0/16:0);Pino(32:0);Phosphatidylinositol(16:0/16:0);Phosphatidylinositol(32:0)PW_C005826PI1614854917183925019578523331785511121212943831213604071238643981239191191259754951260334811274283901274852061027ManganeseHMDB0001333Manganese is an essential trace nutrient in all forms of life. Physiologically, it. exists as an ion in the body. It is concentrated in cell mitochondria, mostly in the pituitary gland, liver, pancreas, kidney, and bone, influences the synthesis of mucopolysaccharides, stimulates hepatic synthesis of cholesterol and fatty acids, and is a cofactor in many enzymes, including arginase and alkaline phosphatase in the liver.16397-91-4C196102785429035MN%2b325916[Mn++]MnInChI=1S/Mn/q+2WAEMQWOKJMHJLA-UHFFFAOYSA-N54.93854.938049636FDB003636Manganese;Manganese (ii) ion;Manganese(ii);Manganese, ion (mn2+);Manganous ion;Mn(2+);Mn2+PW_C001027Mn2+2744738148649155343227122394325131453941035450120557613360521556113161649717869261607485222118801981193922511958164124712491336015115221306770502947749411177832132779611127826735678490115785243317924729380032368119996406120401122121058124121211407121295383121378419122488405123044135123622118123781119123865398123937455125054376125375479125976495126051490126060297126158299126543481126642478126917501127429390127503507127512205127765388128116206128218209964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N785.5497785.157134455FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD9991145186819232164253176282882518840211881414894216122916224921335825362237232646023646883147411347581048816526810352851025335111549612655111275613118603015560541566082161611616263901647517864991796666107703916371752057321213746522274872239076224118182161188721511899211122962251232824912443151125192271259522612710291127202921302930113041302436233187708029377126133771521347750111377507112775181157754133477615132777263377805432978375345789303317922233679272358800123688003436980714119119958406119999384120051408120107407120432405120453122120490124121278429121298418121417382121489383122748120122776121122802374122823443123066376123087135123166448123849464123868454123976399124047398125348479125378480125429482125474481125697297125979489126107299126277484126891501126920391126968502126987207127011206127310209127432506127602388127840389140790185140799186932FADHHMDB0001197FADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle FADH is involved in harvesting of high-energy electrons from carbon fuels; citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH. (Biochemistry. Berg, Jeremy M. Tymoczko, John L. and Stryer, Lubert. New York: W. H. Freeman and Co. 2002.).1910-41-4C0135244601317877FADH2393487CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=C(N2)C(=O)NC(=O)N1C27H35N9O15P2InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1YPZRHBJKEMOYQH-UYBVJOGSSA-N787.5656787.172784519FDB0224831,5-dihydro-fad;1,5-dihydro-p-5-ester with adenosine;1,5-dihydro-riboflavin 5'-(trihydrogen diphosphate) p'->5'-ester with adenosine;Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine 5'-{3-[d-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate};Adenosine 5-(trihydrogen pyrophosphate);Adenosine pyrophosphate 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'-5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Adenosine pyrophosphate, 5'->5'-ester with 5,10-dihydro-7,8-dimethyl-10-(d-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine;Benzo[g]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Benzo[gr]pteridine riboflavin 5'-(trihydrogen diphosphate) deriv;Dihydro-fad;Dihydroflavine-adenine dinucleotide;Fadh2;Fda;Flavin adenine dinucleotide (reduced);Flavin adenine dinucleotide reduced;Reduced flavine adenine dinucleotidePW_C000932FADH2561710453149042505545398102605615661181626501179748922390772241252322712527249771541347852534580036369117810133120001384121299418122663406122778121123869454125238120125380480125980489126795479126922391127433506128393501353CalciumHMDB0000464Calcium is essential for the normal growth and maintenance of bones and teeth, and calcium requirements must be met throughout life. Requirements are greatest during periods of growth, such as childhood, during pregnancy and when breast-feeding. Long-term calcium deficiency can lead to osteoporosis, in which the bone deteriorates and there is an increased risk of fractures. Adults need between 1,000 and 1,300 mg of calcium in their daily diet. Calcium is essential for living organisms, particularly in cell physiology, and is the most common metal in many animals. Physiologically, it exists as an ion in the body. Calcium combines with phosphorus to form calcium phosphate in the bones and teeth. It is essential for the normal functioning of nerves and muscles and plays a role in blood coagulation (as factor IV) and in many enzymatic processes. Calcium is an important component of a healthy diet. A deficit can affect bone and tooth formation, while overretention can cause kidney stones. Vitamin D is needed to absorb calcium. Dairy products, such as milk and cheese, are a well-known source of calcium. However, some individuals are allergic to dairy products and even more people, particularly those of non-European descent, are lactose-intolerant, leaving them unable to consume dairy products. Fortunately, many other good sources of calcium exist. These include: seaweeds such as kelp, wakame and hijiki; nuts and seeds (like almonds and sesame); beans; amaranth; collard greens; okra; rutabaga; broccoli; kale; and fortified products such as orange juice and soy milk. Calcium has also been found to assist in the production of lymphatic fluids.14127-61-8C0007627129108CA%2b2266DB01373[Ca++]CaInChI=1S/Ca/q+2BHPQYMZQTOCNFJ-UHFFFAOYSA-N40.07839.962591155FDB003513Ca;Calcium element;Ca(2+);Ca2+;Calcium ion;Calcium, doubly charged positive ionPW_C000353Ca2+27616303855314601294115993219973510463116346116447147849149142155243211658213817279618293793159713160723942294186664782104822285340111578010171792057232211725816072811901177421311837198118422101219816412215285152881511535030869336177389331776001157815413278266356785263457872413078908114804137480589228818265112022012212046540512104912412130041812137741912185038312192312512237040912289513512309937612361311812387045412393645512440339812447613612492413712557129712571147812598148912600929912605049012653349512720320912743450612746038812750250712810539014067679014067783414069550714Acetylcholine HMDB0000895Acetylcholine (ACh) is a neurotransmitter. Acetylcholine in vertebrates is the major transmitter at neuromuscular junctions, autonomic ganglia, parasympathetic effector junctions, a subset of sympathetic effector junctions, and at many sites in the central nervous system. Its physiological and pharmacological effects, metabolism, release, and receptors have been well documented in several species. ACh has been considered an important excitatory neurotransmitter in the carotid body (CB). Various nicotinic and muscarinic ACh receptors are present in both afferent nerve endings and glomus cells. Therefore, ACh can depolarize or hyperpolarize the cell membrane depending on the available receptor type in the vicinity. Binding of ACh to its receptor can create a wide variety of cellular responses including opening cation channels (nicotinic ACh receptor activation), releasing Ca2+ from intracellular storage sites (via muscarinic ACh receptors), and modulating activities of K+ and Ca2+ channels. Interactions between ACh and other neurotransmitters (dopamine, adenosine, nitric oxide) have been known, and they may induce complicated responses. Cholinergic biology in the CB differs among species and even within the same species due to different genetic composition. Development and environment influence cholinergic biology. Pharmacological data clearly indicate that both muscarinic and nicotinic acetylcholine receptors have a role in the encoding of new memories. Localized lesions and antagonist infusions demonstrate the anatomical locus of these cholinergic effects, and computational modeling links the function of cholinergic modulation to specific cellular effects within these regions. Acetylcholine has been shown to increase the strength of afferent input relative to feedback, to contribute to theta rhythm oscillations, activate intrinsic mechanisms for persistent spiking, and increase the modification of synapses. These effects might enhance different types of encoding in different cortical structures. In particular, the effects in entorhinal and perirhinal cortex and hippocampus might be important for encoding new episodic memories. The role of ACh in attention has been repeatedly demonstrated in several tasks. Acetylcholine is linked to response accuracy in voluntary and reflexive attention and also to response speed in reflexive attention. It is well known that those with Attention-deficit/hyperactivity disorders tend to be inaccurate and slow to respond. (PMID: 17284361, 17011181, 15556286).51-84-3C0199618715355ACETYLCHOLINE182DB03128CC(=O)OCC[N+](C)(C)CC7H16NO2InChI=1S/C7H16NO2/c1-7(9)10-6-5-8(2,3)4/h5-6H2,1-4H3/q+1OIPILFWXSMYKGL-UHFFFAOYSA-N146.2074146.118103761FDB012191Ach;Acetyl choline ion;Acetylcholine cation;Acetylcholinium: acetyl-choline;Choline acetate;Choline acetate (ester);O-acetylcholinePW_C000714ACh1496147852911512130540512387537612598647812743920965CholineHMDB0000097Choline 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-N104.1708104.107539075FDB000710(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_C000065Choline5623564155658149714561211956191376849712185151121971641227822615339215380497761411277619114785301157997213279980331948291249485938311328538811554111811575339812048940712049740912130640512387637612598747812647148112744020912804020643034CDP-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-N488.324488.107330718Audes;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-C121951641528615115335279959132948151241132713881155281186391LysoPC(16:0/0:0)HMDB0010382LysoPC(16:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.14863-27-5C0423046060272998 PHOSPHATIDYLCHOLINE405287[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)CC24H50NO7PInChI=1S/C24H50NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h23,26H,5-22H2,1-4H3/t23-/m1/s1ASWBNKHCZGQVJV-HSZRJFAPSA-N495.6301495.332489471C042301-palmitoyl-glycero-3-phosphocholine;1-palmitoyl-lysophosphatidylcholine;Lpc(16:0);Lpc(16:0/0:0);Lypc(16:0);Lypc(16:0/0:0);Lysopc(16:0);Lysopc(16:0/0:0);Lysophosphatidylcholine(16:0);Lysophosphatidylcholine(16:0/0:0);Lysopc a c16:0;(2r)-2-hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate;1-16:0-lysopc;1-16:0-lysophosphatidylcholine;1-hexadecanoyl-2-lysophosphatidylcholine;1-palmitoyl-2-lysophosphatidylcholine;1-palmitoyl-phosphatidylcholine;1-palmitoyl-sn-glycero-3-phosphocholine;1-palmitoylphosphatidylcholine;16:0 lyso-pc;Lpc 16:0/0:0;Lysopc 16:0/0:0;(2r)-2-hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acidPW_C006391LPC16:015021491601889221163924419078532115121311405123881376125993478127445209440PC(16:0/16:0)HMDB0000564PC(16:0/16:0) 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(16:0/16:0), in particular, consists of two hexadecanoyl 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.63-89-8C0015745211072999PHOSPHATIDYLCHOLINE398235[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCC40H80NO8PInChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1KILNVBDSWZSGLL-KXQOOQHDSA-N734.0389733.562155053FDB022121(r)-4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide hydroxide inner salt;(r)-4-hydroxy-n,n,n-trimethyl-10-oxo-7-[(1-oxohexadecyl)oxy]-3,5,9-trioxa-4-phosphapentacosan-1-aminium 4-oxide inner salt;1,2-bis(hexadecanoyl)-sn-glycero-3-phosphocholine;1,2-bis(palmitoyl)-sn-glycero-3-phosphocholine;1,2-dihexadecanoyl-sn-glycerol-3-phosphorylcholine;1,2-dipalmitoyl-3-sn-phosphatidylcholine;1,2-dipalmitoyl-l-3-phosphatidylcholine;1,2-dipalmitoyl-l-a-lecithin;1,2-dipalmitoyl-l-a-phosphatidylcholine;1,2-dipalmitoyl-l-alpha-lecithin;1,2-dipalmitoyl-l-alpha-phosphatidylcholine;1,2-dipalmitoyl-l-lecithin;1,2-dipalmitoyl-l-phosphatidylcholine;1,2-dipalmitoyl-rac-glycero-3-phosphocholine;1,2-dipalmitoyl-sn-3-glycerophosphocholine;1,2-dipalmitoyl-sn-glycero-3-phosphatidylcholine;1,2-dipalmitoyl-sn-glycero-3-phosphocholine;1,2-dipalmitoyl-sn-glycero-3-phosphorylcholine;1,2-dipalmitoyl-sn-glycerol-3-phosphocholine;1,2-dipalmitoyl-sn-glycerophosphocholine;1,2-dipalmitoyl-sn-glycerophosphorylcholine;1,2-dipalmitoyl-sn-glyceryl-3-phosphocholine;1,2-dipalmitoyl-sn-phosphatidylcholine;1,2-dipalmitoylglycero-3-phosphocholine;1,2-l-a-dipalmitoylphosphatidylcholine;1,2-l-alpha-dipalmitoylphosphatidylcholine;Colfosceril palmitate;Dppc;Dihexadecanoyl-sn-glycero-3-phosphocholine;Dipalmitoyl l-a-phosphatidylcholine;Dipalmitoyl l-alpha-phosphatidylcholine;Dipalmitoyl-l-3-glycerylphosphorylcholine;Dipalmitoyl-l-a-lecithin;Dipalmitoyl-l-a-phosphatidylcholine;Dipalmitoyl-l-alpha-lecithin;Dipalmitoyl-l-alpha-phosphatidylcholine;Dipalmitoyl-sn-3-phosphatidylcholine;Dipalmitoylphosphatidylcholine;Gpcho(16:0/16:0);Gpcho(32:0);L-1,2-dipalmitoyl-a-lecithin;L-1,2-dipalmitoyl-alpha-lecithin;L-1,2-dipalmitoylphosphatidylcholine;L-dppc;L-dipalmitoyl lecithin;L-a-1,2-dipalmitoyl lecithin;L-a-dppc;L-a-dipalmitoylecithin;L-a-dipalmitoyllecithin;L-a-dipalmitoylphosphatidylcholine;L-alpha-1,2-dipalmitoyl lecithin;L-alpha-dppc;L-alpha-dipalmitoylecithin;L-alpha-dipalmitoyllecithin;L-alpha-dipalmitoylphosphatidylcholine;L-b,g-dipalmitoyl-a-lecithin;L-b,g-dipalmitoyl-a-phosphatidylcholine;L-b,g-dipalmitoyl-alpha-lecithin;L-b,g-dipalmitoyl-alpha-phosphatidylcholine;L-b,g-dipalmitoylphosphatidylcholine;Lecithin;Pc aa c32:0;Pc(32:0);Phosphatidylcholine(16:0/16:0);Phosphatidylcholine(32:0);Sn-3-dipalmitoyllecithin;B,g-dipalmitoyl l-a-phosphatidylcholine;B,g-dipalmitoyl l-alpha-phosphatidylcholine;B,g-dipalmitoyl-l-(a)-lecithin;B,g-dipalmitoyl-l-phosphatidylcholine;1,2-dipalmitoylphosphatidylcholine;1-16:0-2-16:0-phosphatidylcholine;16:0-16:0-pc;Colfoscerili palmitas;Dipalmitoyl phosphatidylcholine;Gpcho 16:0/16:0;Palmitate de colfosceril;Palmitato de colfoscerilo;Pc 16:0/16:0;Pc(16:0/16:0);Phosphatidylcholine 16:0/16:0;Colfosceril palmitic acid;Palmitic acid de colfoscerilPW_C000440PC32:05992645161507141570491572189219163977219515300151153052491532028515390309785331157855013080752253890593618906033194848386948493831156814011156823981213144051213581251238843761239171361259964781260313001274482091274833951202PhosphorylcholineHMDB0001565Phosphorylcholine 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-O184.1507184.073869485FDB022692Choline 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_C001202CHOP15112216743497687239214121841517853413278875356948131241132693881155261181220924191246434551259972991262494901278115073149DG(16:0/16:0)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-N568.9114568.506675286FDB0242921,2-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_C003149DG32:0152543210910214358218415913616092241709259195127811511529928515385497803633278040350780591147853535681813331938583831105973901156723981213184191213911231213964331214264091238884551239504471239554681239841371259994901274505074971PE(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-N691.972691.515205345C003501,2-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_C004971PE1615551415664991492499260163976919515297151153212851538730915392177853811578543331807372538889523189055134890563619484238394844384948453861156733981156761211156774011213244051238943761260054781260154951274562091274673907100LysoPE(16:0/0:0)HMDB0011503LysoPE(16:0/0:0) 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.58177710730047826019[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OCCNC21H44NO7PInChI=1S/C21H44NO7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-21(24)27-18-20(23)19-29-30(25,26)28-17-16-22/h20,23H,2-19,22H2,1H3,(H,25,26)/t20-/m1/s1YVYMBNSKXOXSKW-HXUWFJFHSA-N453.5503453.2855392791-palmitoyl-2-hydroxy-sn-glycero-3-phosphoethanolamine;Hexadecanoyl-lysophosphatidylethanolamine;Lpe(16:0);Lpe(16:0/0:0);Lyso-pe(16:0);Lyso-pe(16:0/0:0);Lysope(16:0);Lysope(16:0/0:0);Lysophosphatidylethanolamine(16:0);Lysophosphatidylethanolamine(16:0/0:0);1-hexadecanoyl-sn-glycero-3-phosphoethanolamine;1-palmitoyl-sn-glycero-3-phosphoethanolamine zwitterion;2-ammonioethyl (2r)-2-hydroxy-3-(palmitoyloxy)propyl phosphate;Pe(16:0/0:0);2-ammonioethyl (2r)-2-hydroxy-3-(palmitoyloxy)propyl phosphoric acidPW_C007100LPE16:015582916118892451907854013212132712412389711812600829912745938872GlycerylphosphorylethanolamineHMDB0000114Glycerylphosphorylethanolamine, also known as gpea, belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group. Glycerylphosphorylethanolamine is soluble (in water) and a moderately acidic compound (based on its pKa). Glycerylphosphorylethanolamine has been found in human brain, prostate and liver tissues. Within the cell, glycerylphosphorylethanolamine is primarily located in the cytoplasm. Glycerylphosphorylethanolamine exists in all living organisms, ranging from bacteria to humans. In humans, glycerylphosphorylethanolamine is involved in phospholipid biosynthesis pathway. Glycerylphosphorylethanolamine is a membrane breakdown product resulting from the cleavage of the lipid group from glycerophosphoethanlomine fatty acids (i.e. phosphatidylethanolamine). It acts as a growth stimulant for hepatocytes.1190-00-7C012332283351017215919NCCOP(O)(=O)OCC(O)COC5H14NO6PInChI=1S/C5H14NO6P/c6-1-2-11-13(9,10)12-4-5(8)3-7/h5,7-8H,1-4,6H2,(H,9,10)JZNWSCPGTDBMEW-UHFFFAOYSA-N215.1415215.055873697FDB0218952-aminoethyl ester 1-glycerophosphoric acid;Gpea;Glycerol 3-phosphoethanolamine;Glycerol 3-phosphorylethanolamine;Glycerophosphoethanolamine;Glycerophosphorylethanolamine;Glyceryl-3-phosphorylethanolamine;Glycerylphosphorylethanolamine;A-glycerophosphorylethanolamine;Alpha-glycerophosphorylethanolaminePW_C000072GPEA156187854111112133012212390013512601029712746220596EthanolamineHMDB0000149Ethanolamine 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-N61.083161.052763851FDB0007691-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_C000096ETA15648914624912174151153262785421117997113294825124113281388115538118121333122123903135126013297127465205477PS(16:0/16:0)HMDB0000614PS(16:0/16:0) 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(16:0/16:0), in particular, consists of two hexadecanoyl 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.3036-82-6C02737308138218303L-1-PHOSPHATIDYL-SERINE2338998DB00144CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCC38H74NO10PInChI=1S/C38H74NO10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-36(40)46-31-34(32-47-50(44,45)48-33-35(39)38(42)43)49-37(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h34-35H,3-33,39H2,1-2H3,(H,42,43)(H,44,45)/t34-,35+/m1/s1KLFKZIQAIPDJCW-GPOMZPHUSA-N735.981735.505034585FDB0221441,2-dipalmitoylglycerophosphorylserine;1,2-dipalmitoylphosphatidylserine;Dl-a-dipalmitoyl phosphatidyl-l-serine;Dl-alpha-dipalmitoyl phosphatidyl-l-serine;Dpps;Dipalmitoyl-dl-a-phosphatidyl-l-serine;Dipalmitoyl-dl-alpha-phosphatidyl-l-serine;Dipalmitoylglycerophosphoserine;Dipalmitoylphosphatidylserine;Ps(32:0);Pser(16:0/16:0);Pser(32:0);Phosphatidylserine (16:0/16:0);Phosphatidylserine (32:0)PW_C000477PS32:0156749915624992551959263163153863091539117785443318905413494843384948673831156751211158163981260164951274683908389PGP(16:0/16:0)HMDB0013472PGP(16:0/16:0) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.C038924985959837393L-1-PHOSPHATIDYL-GLYCEROL-P[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC38H76O13P2InChI=1S/C38H76O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(40)47-33-36(34-50-53(45,46)49-32-35(39)31-48-52(42,43)44)51-38(41)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39H,3-34H2,1-2H3,(H,45,46)(H2,42,43,44)/t35-,36+/m0/s1ONJBJMDJKLHMEK-MPQUPPDSSA-N802.961802.4761165031,2-dipalmitoyl-rac-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate);3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid;Pgp(16:0/16:0);Pgp(32:0)PW_C008389PGP161574436250177854513385379134947903841085522231107013911213384061216701211239071201260194791274715016578PG(16:0/16:0)HMDB0010570PG(16:0/16:0) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(16:0/16:0), in particular, consists of two hexadecanoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.C0034444644073205L-1-PHOSPHATIDYL-GLYCEROL393791[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC38H75O10PInChI=1S/C38H75O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h35-36,39-40H,3-34H2,1-2H3,(H,43,44)/t35-,36+/m0/s1BIABMEZBCHDPBV-MPQUPPDSSA-N722.982722.5097856131,2-dihexadecanoyl-rac-glycero-3-phospho-(1'-rac-glycerol);1,2-dipalmitoyl-rac-glycero-3-phosphoglycerol;Gpg(16:0/16:0);Gpg(32:0);Pg(16:0/16:0);Pg(32:0);Phosphatidylglycerol(16:0/16:0);Phosphatidylglycerol(32:0);1,2-dihexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol);1,2-dihexadecanoylphosphatidylglycerol;1,2-dipalmitoylphosphatidylglycerol;Dihexadecanoylphosphatidylglycerol;DipalmitoylphosphatidylglycerolPW_C006578PG16157739150224362521778546112853801349479538410855522311070239112134340712167312112390911912602148112747320636841CL(16:0/16:0/16:0/16:0)HMDB0056387CL(16:0/16:0/16:0/16:0) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(16:0/16:0/16:0/16:0) contains four chains of hexadecanoic acid at the C1, C2, C3 and C4 positions. While the theoretical charge of cardiolipins is -2, under normal physiological conditions (pH near 7), the molecule may carry only one negative charge. In prokaryotes such as E. coli, the enzyme known as diphosphatidylglycerol synthase catalyses the transfer of the phosphatidyl moiety of one phosphatidylglycerol to the free 3'-hydroxyl group of another, with the elimination of one molecule of glycerol. In E. coli, which acylates its glycerophospholipids with acyl chains ranging in length from 12 to 18 carbons and possibly containing an unsaturation, or a cyclopropane group more than 100 possible CL molecular species are theoretically possible, 53 of these species having been characterized. E. coli membranes consist of ~5% cardiolipin (CL), 20-25% phosphatidylglycerol (PG), and 70-80% phosphatidylethanolamine (PE) as well as smaller amounts of phosphatidylserine (PS). CL is distributed between the two leaflets of the bilayers and is located preferentially at the poles and septa in E. coli and other rod-shaped bacteria. It is known that the polar positioning of the proline transporter ProP and the mechanosensitive ion channel MscS in E. coli is dependent on CL. It is believed that cell shape may influence the localization of CL and the localization of certain membrane proteins.C059804985969228494CARDIOLIPIN[H]C(O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC73H142O17P2InChI=1S/C73H142O17P2/c1-5-9-13-17-21-25-29-33-37-41-45-49-53-57-70(75)83-63-68(89-72(77)59-55-51-47-43-39-35-31-27-23-19-15-11-7-3)65-87-91(79,80)85-61-67(74)62-86-92(81,82)88-66-69(90-73(78)60-56-52-48-44-40-36-32-28-24-20-16-12-8-4)64-84-71(76)58-54-50-46-42-38-34-30-26-22-18-14-10-6-2/h67-69,74H,5-66H2,1-4H3,(H,79,80)(H,81,82)/t68-,69-/m1/s1GRTNLBQYBYZCCM-ULKDXPJMSA-N1353.871352.9722271081'-[1,2-dipalmitoyl-rac-glycero-3-phospho],3'-[1,2-dipalmitoyl-rac-glycero-3-phospho]-glycerol;Cl(1'-[16:0/16:0],3'-[16:0/16:0]);Cl(16:0/16:0/16:0/16:0);Cl(64:0);Cardiolipin(16:0/16:0/16:0/16:0);Cardiolipin(64:0)PW_C036841CL161580384041628406197915222436256177854811285382134948003841085582231107043911213494071216771211239121191260244811274762061144NADHHMDB0001487NADH 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-N665.441665.124771695FDB0226491,4-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_C001144NADH14341533490864810111521275514695422304927811728362931099480618481218482128490464959315169955240103533211153581125466123547912555931355698100573710858291415915147594515160271556079161638716472178677111768931607011188709916371722057195206746222282442268360225908622411809198118212161232024913003298130153001325522342403322426183157710713277123133772081347737133177651336776683347770033277707130779171137798634780009368806911199382212411054938811285494115838118119955406120172407120378122120986408121162425121244126121693429121818383122616384122745120123127447123138136123551374123734460123814443124242464124371398125189121125345479125531481125762297125808299125926482126516495126767480126888501127385502128090390128362391128429395140759185721NADHMDB0000902NAD (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]1OC21H27N7O14P2InChI=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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N663.4251663.109121631FDB0223093-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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951407571851031Palmitoyl-CoAHMDB0001338Palmitoyl-CoA, also known as palmityl 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@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=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-BBECNAHFSA-N1005.9431005.344873947FDB022562Hexadecanoyl 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_C001031COA16:087538802289017164714209010209625229102524410469581626970199712916372011609123170912918892141952550349772191347722732977893112780453327804913278549115792573338184433190767210957063839712038210859728811110338911420539012022838412066440712135640512140412312141112412290112112291439912327811912391537612396344712397011812557648012558948412602648112602847812620829912710639112747820612748020912777038812884739814074818614076489114691-Acyl-sn-glycerol-3-phosphate acyltransferase alphaQ99943Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
HMDBP01581AGPAT16p21.3CR81247812.3.1.5114814914954221081021415833431133521846212138420213138424756711Phosphatidate cytidylyltransferase 1Q92903Provides CDP-diacylglycerol an important precursor for the synthesis of phosphatidylinositol (PtdIns), phosphatidylglycerol, and cardiolipin. Overexpression may amplify cellular signaling responses from cytokines. May also play an important role in the signal transduction mechanism of retina and neural cells.
HMDBP00764CDS14q21.23AK31424512.7.7.41148449138421213717CDP-diacylglycerol--inositol 3-phosphatidyltransferaseO14735Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due to the reverse reaction of PtdIns synthase and is dependent on CMP, which is tightly bound to the enzyme.
HMDBP00771CDIPT16p11.2BC00144412.7.8.111487492514141384222131434841008192Glycerol-3-phosphate dehydrogenase, mitochondrialP43304HMDBP00197GPD22q24.1U4036211.1.5.3104731479491492422117584624221384237561445691285498AcetylcholinesteraseP22303Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
HMDBP00524ACHE7q22CH23695613.1.1.714981413842521114261637143603105914558395025Choline O-acetyltransferaseP28329Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
HMDBP00025CHAT10q11.2AF30589512.3.1.614992138426160141371481419761841425807891429053914360210602620Glycerophosphodiester phosphodiesterase 1Q9NZC3Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
HMDBP07388GDE116p12-p11.2AF21286213.1.4.44150121565813842716013844219854Acyl-protein thioesterase 1O75608Hydrolyzes fatty acids from S-acylated cysteine residues in proteins such as trimeric G alpha proteins or HRAS. Has depalmitoylating activity and also low lysophospholipase activity.
HMDBP00056LYPLA18q11.23BC01039713.1.2.-1503141562813842821113844019855Group XV phospholipase A2Q8NCC3Has transacylase and calcium-independent phospholipase A2 activity. Catalyzes the formation of 1-O-acyl-N-acetylsphingosine and the concomitant release of a lyso-phospholipid (By similarity). May have weak lysophospholipase activity.
HMDBP00057PLA2G15CH47109212.3.1.-1504141563213842921113844116070Group IID secretory phospholipase A2Q9UNK4PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
HMDBP00073PLA2G2D1p36.12AF18862513.1.1.4150814156021384302111384391604323Cytosolic phospholipase A2 betaP0C869Calcium-dependent phospholipase A2 that selectively hydrolyzes glycerophospholipids in the sn-2 position with a preference for arachidonoyl phospholipids. Has a much weaker activity than PLA2G4A. Isoform 3 has calcium-dependent activity against palmitoyl-arachidonyl-phosphatidylethanolamine and low level lysophospholipase activity but no activity against phosphatidylcholine. Isoform 5 does have activity against phosphatidylcholine.
HMDBP09120PLA2G4B15q11.2-q21.3AC02065913.1.1.430281509141559213843121113843816013914480140941602243Phosphoethanolamine/phosphocholine phosphataseQ8TCT1Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
HMDBP03097PHOSPHO117q21.32AC00479713.1.3.75151321384321602128Cholinephosphotransferase 1Q8WUD6Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes.
HMDBP02855CHPT112qCH47105412.7.8.215304341278497556138433214227Diacylglycerol kinase alphaP23743Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activityHMDBP00233DGKA12q13.3AF06477112.7.1.1071536142114102162581130418113448166138434211145783818231Lipid phosphate phosphohydrolase 1O14494Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
HMDBP00237PPAP2A5q11AF01440213.1.3.415391433791846191013843521177Phospholipase D2O14939May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
HMDBP00080PLD217p13.1BC01503313.1.4.415561413843621178Phosphatidylethanolamine N-methyltransferaseQ9UBM1Catalyzes three sequential methylation reactions of phosphatidylethanolamine (PE) by AdoMet, thereby producing phosphatidylcholine (PC).
HMDBP00081PEMT17p11.2AF29446612.1.1.17; 2.1.1.7157618155711466621536530980862221384377572173Phosphatidylserine synthase 2Q9BVG9Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. PTDSS2 is specific for phosphatatidylethanolamine and does not act on phosphatidylcholine.
HMDBP02960PTDSS211p15.5AL83435712.7.8.291568491384432131860Phosphatidylserine decarboxylase proenzymeQ9UG56HMDBP02255PISD22q12.2BC00931514.1.1.6515691015371171384442122351CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrialQ32NB8Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin (By similarity).
HMDBP03388PGS117q25.3CH47109912.7.8.51575434816171384451612625Phosphatidylglycerophosphatase and protein-tyrosine phosphatase 1Q8WUK0Lipid phosphatase which dephosphorylates phosphatidylglycerophosphate (PGP) to phosphatidylglycerol (PG). PGP is an essential intermediate in the biosynthetic pathway of cardiolipin, a mitochondrial-specific phospholipid regulating the membrane integrity and activities of the organelle. Has also been shown to display phosphatase activity toward phosphoprotein substrates, specifically mediates dephosphorylation of mitochondrial proteins, thereby playing an essential role in ATP production. Has probably a preference for proteins phosphorylated on Ser and/or Thr residues compared to proteins phosphorylated on Tyr residues. Probably involved in regulation of insulin secretion in pancreatic beta cells (By similarity).
HMDBP07398PTPMT111p11.2AC10494213.1.3.27; 3.1.3.16; 3.1.3.481578334820171384461632350Cardiolipin synthaseQ9UJA2Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol.
HMDBP03379CRLS120p13-p12.3AL03546112.7.8.-158133482317138447163782Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmicP21695HMDBP00837GPD112q12-q13AC02515411.1.1.81044814762138448198141821261445741284783Glycerol-3-phosphate acyltransferase 1, mitochondrialQ9HCL2Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
HMDBP00838GPAM10q25.2AL39198612.3.1.151646320871021355846282213844916311847Choline-phosphate cytidylyltransferase AP49585Controls phosphatidylcholine synthesis.HMDBP00755PCYT1A3q29CH47119112.7.7.151535818153674924687224688813845016011846Choline kinase alphaP35790Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.HMDBP00778CHKA11q13.2BC03647112.7.1.32;2.7.1.8215351213845116011850Phosphatidylserine synthase 1P48651Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.HMDBP02190PTDSS18q22BC00439012.7.8.29;2.7.8.-153774925476181384522104021-acyl-sn-glycerol-3-phosphate acyltransferase alpha1PW_P0004024241469403Phosphatidate cytidylyltransferase 11PW_P0004034257111934231404CDP-diacylglycerol--inositol 3-phosphatidyltransferase1PW_P000404426717194423119510271292Glycerol-3-phosphate dehydrogenase, mitochondrial1PW_P00029231119211309641405Acetylcholinesterase1PW_P000405427498407Choline O-acetyltransferase1PW_P0004074292512614231408Glycerophosphodiester phosphodiesterase 11PW_P00040843026201964231409Acyl-protein thioesterase 11PW_P00040943154410Group XV phospholipase A21PW_P00041043255411Group IID secretory phospholipase A21PW_P00041143370197353177Cytosolic phospholipase A2 beta1PW_P00007791432314335313008413Phosphoethanolamine/phosphocholine phosphatase1PW_P00041343522431984231415Cholinephosphotransferase 11PW_P00041543721281994231417Diacylglycerol kinase alpha1PW_P000417439227418Lipid phosphate phosphohydrolase 11PW_P000418440231424Phospholipase D21PW_P00042444777172Phosphatidylethanolamine N-methyltransferase1PW_P000172190781425Phosphatidylserine synthase 21PW_P0004254482173426Phosphatidylserine decarboxylase proenzyme1PW_P0004264491860428CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase, mitochondrial1PW_P0004284512351430Phosphatidylglycerophosphatase and protein-tyrosine phosphatase 11PW_P0004304532625431Cardiolipin synthase1PW_P0004314542350293Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic1PW_P000293312782224032448Glycerol-3-phosphate acyltransferase 1, mitochondrial1PW_P000448471783414Choline-phosphate cytidylyltransferase A1PW_P00041443611847412Choline kinase alpha1PW_P00041243411846427Phosphatidylserine synthase 11PW_P00042745011850919falsePW_R000919Right368339041Compoundfalse36845311Compoundfalse5014022.3.1.51920falsePW_R000920Right36855311Compoundfalse368630191Compoundfalse5024032.7.7.41921falsePW_R000921Right368730191Compoundfalse368858261Compoundfalse5034042.7.8.11813falsePW_R000813Right3295811Compoundfalse329618601Compoundtrue329711341Compoundfalse329816321Compoundtrue3542921.1.5.3922falsePW_R000922Right36897141Compoundfalse3690651Compoundfalse5054053.1.1.7924falsePW_R000924Right3693651Compoundfalse36947141Compoundfalse5074072.3.1.6925falsePW_R000925Right3695430341Compoundfalse3696811Compoundtrue3697651Compoundfalse5084083.1.4.44926falsePW_R000926Right369863911Compoundfalse3699430341Compoundfalse5094093.1.2.-928falsePW_R000928Right370463911Compoundfalse3705430341Compoundfalse5104102.3.1.-930falsePW_R000930Right37104401Compoundfalse371163911Compoundfalse5114113.1.1.4931falsePW_R000931Right37124401Compoundfalse371363911Compoundfalse512773.1.1.4933falsePW_R000933Right371612021Compoundfalse3717651Compoundfalse5154133.1.3.75935falsePW_R000935Right3721430341Compoundfalse37224401Compoundfalse372331491Compoundfalse5204152.7.8.2938falsePW_R000938Right373231491Compoundfalse37335311Compoundfalse5254172.7.1.107939falsePW_R000939Right37345311Compoundfalse826814201Compoundtrue373531491Compoundfalse826911041Compoundtrue5264183.1.3.4941falsePW_R000941Right37405311Compoundfalse374149711Compoundfalse5324243.1.4.4942falsePW_R000942Right374249711Compoundfalse37434401Compoundfalse533172943falsePW_R000943Right374449711Compoundfalse374571001Compoundfalse534773.1.1.4944falsePW_R000944Right374649711Compoundfalse374771001Compoundfalse5354113.1.1.4945falsePW_R000945Right374871001Compoundfalse3749721Compoundfalse5364093.1.2.-946falsePW_R000946Right375071001Compoundfalse3751721Compoundfalse5374102.3.1.-947falsePW_R000947Right3752721Compoundfalse3753811Compoundfalse3754961Compoundfalse5384083.1.4.44948falsePW_R000948Right375549711Compoundfalse37564771Compoundfalse5394252.7.8.29949falsePW_R000949Right37574771Compoundfalse375849711Compoundfalse5404264.1.1.65951falsePW_R000951Right376130191Compoundfalse376283891Compoundfalse5424282.7.8.5952falsePW_R000952Right376383891Compoundfalse376465781Compoundfalse544430953falsePW_R000953Right376565781Compoundfalse376630191Compoundfalse3767368411Compoundfalse5454312.7.8.-814falsePW_R000814Right329911341Compoundfalse330011441Compoundtrue3301811Compoundfalse33027211Compoundtrue3552931.1.1.8973falsePW_R000973Right3835811Compoundfalse383610311Compoundfalse383739041Compoundfalse826610991Compoundtrue5744482.3.1.15975falsePW_R000975Right384110311Compoundfalse384239041Compoundfalse38435311Compoundfalse826710991Compoundtrue5764022.3.1.51934falsePW_R000934Right371812021Compoundfalse3719430341Compoundfalse5194142.7.7.15932falsePW_R000932Right3714651Compoundfalse371512021Compoundfalse514412950falsePW_R000950Right37594401Compoundfalse37604771Compoundfalse5414272.7.8.2924171134282false131826010regular300280241981282false46826010regular300280242139044982false468123010regular30028024235314982false468176510regular300280242430194982false468248010regular3002802425423499false568221719regular10025242658264982false468305510regular3002802427423499false518286719regular1002524281027499false638286719regular100252429814282false131875510regular300280243096442137false153371010regular5030243193242138false153355510regular50302432353429false141561019regular10025243339044282false1318132010regular30028024355314282false1318195010regular30028024437141482false175841010regular3002802444651482false230341010regular300280244543034281false293845510regular200190244681281false251821010regular200190244742329false268852010regular10025244863911482false351341010regular30028024534401482false351393010regular3002802454353149false349377019regular100252455353149false374877719regular1002524561202282false230897010regular300280245742329false230378219regular10025247443034282false2783142510regular300280249531494382false3513142510regular3002802496423439false3218152010regular1002525055311482false3513200510regular300280253449711482false3513243010regular30028025357100282false3513294010regular300280253635329false3488278019regular10025253735329false3748277719regular10025253872882false3518344510regular300280253981882false2783344510regular300280254096881false3088330510regular200190254142389false3273353510regular10025254249714982false1438358510regular30028025434774982false878358510regular30028025454401882false878408010regular30028025468389482false1093248010regular30028025496578382false1738248010regular30028025503019382false1738303010regular300280255136841382false1368288010regular30028025811144860false112830010regular50302582721859false83830010regular503026581031382false85883510regular300280265910311482false838139510regular3002808961469492false54316158subunitregular15070897711492false54322278subunitregular15070898717492false54328778subunitregular15070899192422false13906208subunitregular150709011469422false139317658subunitregular15070903498142false2108958subunitregular150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1510 C618 1540 618 1585 618 1615 5false183540M618 1765 C618 1735 618 1715 618 1685 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3541M618 2045 C618 2075 618 2197 618 2227 5false183542M618 2480 C618 2450 618 2327 618 2297 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3543M438 700 L438 750 L488 700 z10true183544M618 2760 C618 2790 618 2847 618 2877 5false183545M618 3055 C618 3025 618 2977 618 2947 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3546M438 700 L438 750 L488 700 z10true183547M438 700 L438 750 L488 700 z10true183548M1468 755 C1467 740 1469 708 1465 690 5false183549M1533 725 C1503 725 1466 719 1465 690 5false183550M1468 540 C1468 568 1465 592 1465 620 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3551M1533 570 C1502 568 1466 575 1465 620 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3552M1145.5 1040 L1145.5 1090 L1195.5 1040 z10true183556M1468 1600 C1468 1630 1468 1735 1468 1765 5false183557M1468 1950 C1468 1920 1468 1865 1468 1835 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3575M1908 410 C1908 358 1908 204 1906 131 C1962 132 2049 129 2108 130 5false183576M2453 410 C2451 284 2450 209 2450 127 C2377 128 2291 130 2248 130 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3577M2303 550 C2277 550 2283 550 2253 550 5false183578M2058 550 C2083 550 2073 550 2103 550 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3579M2938 550 C2908 550 2843 550 2813 550 5false183580M2618 400 C2618 425 2619 550 2663 550 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3581M2603 550 C2642 550 2633 550 2663 550 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3582M2048 655 L2048 705 L2098 655 z10true183583M3512 495 C3482 495 3438 495 3408 495 5false183584M3140 496 C3213 494 3218 495 3248 495 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3585M3511 604 C3481 604 3430 605 3400 605 5false183586M3145 605 C3200 606 3220 605 3250 605 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3591M3543 927 C3543 897 3543 885 3543 855 5false183592M3543 694 C3543 721 3543 755 3543 785 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3593M2593 970 L2593 1020 L2643 970 z10true183594M3798 929 C3798 899 3798 887 3798 857 5false183595M3799 694 C3799 719 3798 757 3798 787 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3596M438 700 L438 750 L488 700 z10true183599M2358 969 C2358 939 2358 892 2358 862 5false183600M2358 792 C2358 767 2357 716 2358 691 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3601M438 700 L438 750 L488 700 z10true183670M3083 1565 C3113 1565 3148 1565 3178 1565 5false183671M3663 1210 C3660 1310 3383 1548 3328 1565 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3672M3513 1565 C3482 1565 3358 1565 3328 1565 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3673M2398 1375 L2398 1425 L2448 1375 z10true183684M3539 1705 C3539 1735 3538 1780 3538 1810 5false183685M3540 1999 C3540 1963 3539 1912 3538 1880 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3690M3798 2005 C3798 1975 3798 1910 3798 1880 5false183691M3798 1710 C3798 1736 3798 1780 3798 1810 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3724M3663 2285 C3663 2315 3663 2290 3663 2320 5false183725M3663 2430 C3663 2405 3663 2422 3663 2390 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3726M3513 2570 C3363 2570 3162 2568 3093 2565 5false183727M3513 1070 C2004 1068 2840 2564 2943 2565 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3728M3538 2711 C3538 2741 3538 2765 3538 2795 5false183729M3539 2937 C3539 2908 3538 2895 3538 2865 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3730M2843 2730 L2843 2780 L2893 2730 z10true183731M3798 2711 C3798 2741 3798 2762 3798 2792 5false183732M3799 2936 C3799 2902 3798 2892 3798 2862 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3733M438 700 L438 750 L488 700 z10true183734M3538 3220 C3538 3249 3538 3260 3538 3290 5false183735M3540 3442 C3538 3409 3538 3400 3538 3370 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3736M3798 3220 C3798 3250 3798 3265 3798 3295 5false183737M3800 3442 C3800 3406 3799 3395 3798 3365 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3738M3518 3585 C3488 3585 3428 3585 3398 3585 5false183739M3083 3585 C3112 3585 3218 3585 3248 3585 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3740M3188 3495 C3188 3519 3199 3584 3248 3585 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3741M438 700 L438 750 L488 700 z10true183742M1588 3585 C1588 3520 1413 3490 1383 3490 5false183743M1028 3585 C1031 3487 1203 3490 1233 3490 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3744M1178 3725 C1197 3723 1213 3727 1235 3725 5false18falsefalse3745M1438 3725 C1409 3725 1405 3725 1375 3725 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3750M768 2620 C828 2618 850 2621 888 2620 5false183751M1093 2620 C1073 2620 1066 2621 1038 2620 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3755M1393 2620 C1416 2620 1425 2620 1448 2620 5false183756M1738 2620 C1718 2620 1622 2620 1598 2620 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3757M1888 2760 C1887 2793 1888 2820 1888 2850 5false183758M1888 3030 C1889 2942 1888 2950 1888 2920 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3759M1668 3020 C1725 3020 1888 2950 1888 2920 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3809M1318 400 C1288 400 1128 400 1098 400 5false183810M1153 330 C1151 357 1128 400 1098 400 5false183811M768 400 C794 399 913 400 938 400 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345falsefalsefalse3812M863 330 C864 379 908 400 938 400 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3915M618 540 C618 570 618 1080 618 1110 5false183916M858 975 C785 984 669 1030 618 1110 5false183917M618 1230 C618 1200 618 1210 618 1180 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3918M1158 975 C1244 976 1466 1100 1468 1200 5false183919M1468 1035 C1468 1065 1468 1170 1468 1200 5false183920M1468 1320 C1468 1290 1468 1300 1468 1270 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false3921M838 1535 C805 1536 647 1553 618 1615 5false183922M618 1510 C618 1540 618 1585 618 1615 5false183923M618 1765 C618 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