25105PathwayDe Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other animals, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils. (Wikipedia) De novo biosynthesis of triglycerides is also known as the phosphatidic acid pathway, and it is mainly associated with the liver and adipose tissue. All membrane-localized enzymes are coloured dark green in the image. First, dihydroxyacetone phosphate (or glycerone phosphate) from glycolysis is used by the cytosolic enzyme glycerol-3-phosphate dehydrogenase [NAD(+)] to synthesize sn-glycerol 3-phosphate. Second, the mitochondrial outer membrane enzyme glycerol-3-phosphate acyltransferase esterifies an acyl-group to the sn-1 position of sn-glycerol 3-phosphate to form 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LPA). The next three steps are localized to the endoplasmic reticulum membrane. The enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. Next, magnesium-dependent phosphatidate phosphatase catalyzes the conversion of phosphatidic acid into diacylglycerol. Last, the enzyme diacylglycerol O-acyltransferase synthesizes triacylglycerol from diacylglycerol and a fatty acyl-CoA.MetabolicPW025287CenterPathwayVisualizationContext2557014492101#000099PathwayVisualization2504125105De Novo Triacylglycerol Biosynthesis TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other animals, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils. (Wikipedia) De novo biosynthesis of triglycerides is also known as the phosphatidic acid pathway, and it is mainly associated with the liver and adipose tissue. All membrane-localized enzymes are coloured dark green in the image. First, dihydroxyacetone phosphate (or glycerone phosphate) from glycolysis is used by the cytosolic enzyme glycerol-3-phosphate dehydrogenase [NAD(+)] to synthesize sn-glycerol 3-phosphate. Second, the mitochondrial outer membrane enzyme glycerol-3-phosphate acyltransferase esterifies an acyl-group to the sn-1 position of sn-glycerol 3-phosphate to form 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LPA). The next three steps are localized to the endoplasmic reticulum membrane. The enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase converts LPA into phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by esterifying an acyl-group to the sn-2 position of the glycerol backbone. Next, magnesium-dependent phosphatidate phosphatase catalyzes the conversion of phosphatidic acid into diacylglycerol. Last, the enzyme diacylglycerol O-acyltransferase synthesizes triacylglycerol from diacylglycerol and a fatty acyl-CoA.Metabolic11596176GlycolysisSubPathway150301134Compound25532818238778Chen YQ, Kuo MS, Li S, Bui HH, Peake DA, Sanders PE, Thibodeaux SJ, Chu S, Qian YW, Zhao Y, Bredt DS, Moller DE, Konrad RJ, Beigneux AP, Young SG, Cao G: AGPAT6 is a novel microsomal glycerol-3-phosphate acyltransferase. J Biol Chem. 2008 Apr 11;283(15):10048-57. doi: 10.1074/jbc.M708151200. Epub 2008 Jan 31.25105Pathway5532921873652Agarwal AK, Sukumaran S, Cortes VA, Tunison K, Mizrachi D, Sankella S, Gerard RD, Horton JD, Garg A: Human 1-acylglycerol-3-phosphate O-acyltransferase isoforms 1 and 2: biochemical characterization and inability to rescue hepatic steatosis in Agpat2(-/-) gene lipodystrophic mice. J Biol Chem. 2011 Oct 28;286(43):37676-91. doi: 10.1074/jbc.M111.250449. Epub 2011 Aug 27.25105Pathway5533016214399Orland MD, Anwar K, Cromley D, Chu CH, Chen L, Billheimer JT, Hussain MM, Cheng D: Acyl coenzyme A dependent retinol esterification by acyl coenzyme A: diacylglycerol acyltransferase 1. Biochim Biophys Acta. 2005 Oct 15;1737(1):76-82. doi: 10.1016/j.bbalip.2005.09.003. Epub 2005 Sep 20.25105Pathway553318944226Lehner R, Kuksis A: Biosynthesis of triacylglycerols. Prog Lipid Res. 1996;35(2):169-201.25105Pathway1CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman2Bacteria2ProkaryoteBacteria3Escherichia coli562Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm10Drosophila melanogaster7227EukaryoteFruit fly23Pseudomonas aeruginosa287Prokaryote60Nitzschia sp.0001EukaryoteNitzschia425Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast3Mitochondrial MatrixGO:00057592MitochondrionGO:00057395CytoplasmGO:00057377Endoplasmic Reticulum MembraneGO:00057891CytosolGO:00058294PeroxisomeGO:000577712Mitochondrial Inner MembraneGO:00057436LysosomeGO:000576413Endoplasmic ReticulumGO:000578316Lysosomal LumenGO:004320235ChloroplastGO:000950711Extracellular SpaceGO:000561514Mitochondrial Outer MembraneGO:000574124Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562010Cell MembraneGO:000588636MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025825Golgi apparatusGO:000579427Peroxisome MembraneGO:00057788Smooth Endoplasmic Reticulum GO:000579018Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563440PeriplasmGO:004259719sarcoplasmic reticulumGO:00165291LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous SystemBTO:000148411HeartBTO:000056273104311PW_BS0000043211PW_BS0000038511PW_BS000008101711PW_BS0000102111PW_BS0000025411PW_BS000005541315PW_BS00005449711PW_BS000049171211PW_BS00001729111PW_BS0000299611PW_BS000009181311PW_BS0000182811611PW_BS0000286131PW_BS000006311511PW_BS000031951721PW_BS000095103331PW_BS0001031115121PW_BS0001111122121PW_BS0001121231751PW_BS0001231251351PW_BS0001251355171PW_BS000135100521PW_BS00010010813PW_BS00010814117191PW_BS0001411471241PW_BS000147151141PW_BS0001511553241PW_BS0001551613181PW_BS00016111PW_BS0000011783211PW_BS000178117131PW_BS0001171601181PW_BS000160188118PW_BS0000241632181PW_BS000163205561PW_BS000024206261PW_BS000024222341PW_BS000024226441PW_BS0000242253541PW_BS000024224241PW_BS0000241985181PW_BS0000242164181PW_BS0000242491341PW_BS00002429817101PW_BS00002430013101PW_BS0000242231241PW_BS0000243221231PW_BS000024315123PW_BS0000241321121PW_BS0001321333121PW_BS00013313412121PW_BS0001343317121PW_BS0000283361121PW_BS0000283344121PW_BS00002833217121PW_BS00002813013121PW_BS0001301136121PW_BS00011334713125PW_BS0000283683601PW_BS0000281192171PW_BS000119124151PW_BS000124388161PW_BS000112943PW_BS0000941181171PW_BS000118406351PW_BS000115407251PW_BS000115122551PW_BS000122408451PW_BS0001154251355PW_BS000115126651PW_BS000126429151PW_BS000115383751PW_BS0001003841251PW_BS0001001203171PW_BS00012044717171PW_BS00011513613171PW_BS0001363744171PW_BS00005346013175PW_BS0001154436171PW_BS0001154641171PW_BS0001153987171PW_BS00011312112171PW_BS0001214793101PW_BS0001154812101PW_BS0001152975101PW_BS0000242991101PW_BS0000244824101PW_BS0001154957101PW_BS00011548012101PW_BS000115501361PW_BS000115502461PW_BS000115390761PW_BS0001123911261PW_BS0001123951361PW_BS00011315111PW_BS000015261115PW_BS000026221411PW_BS000022422411PW_BS0000427028511PW_BS000070107313PW_BS000107105113PW_BS0001051572241PW_BS00015715924PW_BS00015916611PW_BS00016615284PW_BS000152101531PW_BS0001011873118PW_BS000024219314PW_BS00002422014PW_BS0000242137181PW_BS00002421013181PW_BS00002421217181PW_BS00002417018PW_BS00017016212181PW_BS0001621951318PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS0000242941141PW_BS0000243081011PW_BS0000243183123PW_BS0000243125231PW_BS0000243201123PW_BS00002429341PW_BS0000241141112PW_BS00011432711125PW_BS00002834524121PW_BS000028310312PW_BS00002430412PW_BS000024109323PW_BS000109409115PW_BS0001154241155PW_BS0001154182451PW_BS0001151371117PW_BS00013745911175PW_BS00011545424171PW_BS0001154831110PW_BS00011548924101PW_BS000115208116PW_BS0000245062461PW_BS000115432511PW_BS00004335625121PW_BS0000284192551PW_BS00011545525171PW_BS00011549025101PW_BS0001155072561PW_BS0001155811411PW_BS000058350114121PW_BS000028253541PW_BS00002443311451PW_BS000115468114171PW_BS00011532914121PW_BS0000283821451PW_BS0001002881441PW_BS0000243891461PW_BS000112592711PW_BS000059111811PW_BS00001114101PW_BS0000141021231PW_BS0001021041431PW_BS00010419914181PW_BS00002412915121PW_BS0001291151012PW_BS00011533527121PW_BS0000283331212PW_BS0000283761017PW_BS00005339914171PW_BS000113405105PW_BS0001154141551PW_BS0001154222751PW_BS00011545015171PW_BS00011537527171PW_BS0000534781010PW_BS00011548414101PW_BS00011549127101PW_BS000115209106PW_BS0000245082761PW_BS00011513121PW_BS000013204111PW_BS000020331811PW_BS0000332441011PW_BS00002460251PW_BS00006046114PW_BS00004672513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097110231PW_BS00011012711651PW_BS000127140103PW_BS00014014315191PW_BS0001431465191PW_BS0001461802211PW_BS000180207661PW_BS0000242111018PW_BS00002421425181PW_BS0000242156181PW_BS0000241901118PW_BS0000242771218PW_BS00002465111PW_BS0000652905491PW_BS0000242916491PW_BS0000242924491PW_BS0000243016101PW_BS000024302116101PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS0000283522512PW_BS00002835325127PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS0001154151851PW_BS00011543441051PW_BS000115436255PW_BS0001154461217PW_BS000115448116171PW_BS00011545118171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS00011548718101PW_BS0001155041861PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS000047231511PW_BS000023241529PW_BS00002425715291PW_BS0000241144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid665.441665.124771695-2.358NADH0-2FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH1434153349086481011152127551469542230492781172836293109948061848121848212849046495931516995524010353321115358112546612354791255593135569810057371085829141591514759451516027155607916163871647217867711176893160701118870991637172205719520674622228244226836022590862241180919811821216123202491300329813015300132552234240332242618315771071327712313377208134773713317765133677668334777003327770713077917113779863478000936880691119938221241105493881128549411583811811995540612017240712037812212098640812116242512124412612169342912181838312261638412274512012312744712313813612355137412373446012381444312424246412437139812518912112534547912553148112576229712580829912592648212651649512676748012688850112738550212809039012836239112842939540034Hydrogen IonHMDB0059597Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [WikiPedia])C000801038153781010[H+]HInChI=1S/p+1GPRLSGONYQIRFK-UHFFFAOYSA-Nhydron1.00791.0078250320hydron10H+;H(+);Hydrogen cation;Hydron;ProtonPW_C040034H+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951134Dihydroxyacetone phosphateHMDB0001473Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.57-04-5C0011166816108DIHYDROXY-ACETONE-PHOSPHATE648DB04326OCC(=O)COP(O)(O)=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)GNGACRATGGDKBX-UHFFFAOYSA-N(3-hydroxy-2-oxopropoxy)phosphonic acid170.0578169.998024468-0.893dihydroxyacetone-phosphate0-2FDB0016181,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acidPW_C001134Dhapp1026814742330554253425813108590814759361516884160426603157709813277934111783743457855933493824124110551388115839118120733122122564418122590408123333135125137454125162374125787297125950299126712489126736482127242205128303506128330502721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-O1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium664.433664.116946663-2.5981-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium1-1FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD1404150335386511011142113443127351466542229492779172835293107948071848131848192849026496031516795523810353341115360112546912354821255590135561011856961005738108582714159121475942151602415560721576076161638516469178677211768901607012188709716371742057197206740519874592228241226835922590852241181921612322249130062981301830013256223424043224261931577104132771201337720913477370331776503367766733477702332777091307791511377983347784063568000636880690119938251241105523881127501661128539411992912211995240612017140712083441912098440812115942512124212612125942912181738312261438412274212012313044712314113612341945512354937412373146012381244312382946412437039812518712112531929712534247912553048112580629912582549012592448212651549512676548012688550112727850712738350212808939012836039112842839581Glycerol 3-phosphateHMDB0000126Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).17989-41-2C0009343916215978GLYCEROL-3P388308DB02515OC[C@@H](O)COP(O)(O)=OC3H9O6PInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1AWUCVROLDVIAJX-GSVOUGTGSA-N[(2R)-2,3-dihydroxypropoxy]phosphonic acid172.0737172.013674532-0.7543-phosphoglycerol0-2FDB0218001-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acidPW_C000081Glyc1P1043814752148842211558629510762961088412162912217010653188125461511255022315319249348141742466318424673157803011178052350783723457837813279952134818082539382612494789384110553388110636391115840118120756122121297418121345121121415433123353135123867454123974468125788297125978489125991299127243205127431506839Linoleoyl-CoAHMDB0001064Linoleoyl-CoA is the acyl-CoA of linoleic acid found in the human body. It binds to and results in decreased activity of Glutathione S-transferase1. It has been proposed that inhibition of mitochondrial adenine nucleotide translocator by long chain acyl-CoA underlies the mechanism associating obesity and type 2 diabetes. Unsaturated fatty acids play an important role in the prevention of human diseases such as diabetes, obesity, cancer, and neurodegeneration. Their oxidation in vivo by acyl-CoA dehydrogenases (ACADs) catalyze the first step of each cycle of mitochondrial fatty acid {beta}-oxidation; ACAD-9 had maximal activity with long-chain unsaturated acyl-CoAs as substrates. (PMID: 17184976, 16020546).6709-57-5C02050546216415530CPD-1810637815CCCCC\C=C/C\C=C/CCCCCCCC(=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=C2NC39H66N7O17P3SInChI=1S/C39H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-/t28-,32-,33-,34+,38-/m1/s1YECLLIMZHNYFCK-RRNJGNTNSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(9Z,12Z)-octadeca-9,12-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid1029.971029.344875861-3.089linoleoyl-coa0-4FDB022403(9z,12z)-octadecadienoyl-coa;(9z,12z)-octadecadienoyl-coenzyme a;Linoleoyl-coa;Linoleoyl-coenzyme a;CoA(18:2(9Z,12Z))PW_C000839LC25514492566322818563318507532995716383989153821089342881115233891142173901288573981099Coenzyme AHMDB0001423Coenzyme A (CoA, CoASH, or HSCoA) is a coenzyme notable for its role in the synthesis and oxidization of fatty acids and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate, and adenosine triphosphate. It is also a parent compound for other transformation products, including but not limited to, phenylglyoxylyl-CoA, tetracosanoyl-CoA, and 6-hydroxyhex-3-enoyl-CoA. Coenzyme A is synthesized in a five-step process from pantothenate and cysteine. In the first step pantothenate (vitamin B5) is phosphorylated to 4'-phosphopantothenate by the enzyme pantothenate kinase (PanK, CoaA, CoaX). In the second step, a cysteine is added to 4'-phosphopantothenate by the enzyme phosphopantothenoylcysteine synthetase (PPC-DC, CoaB) to form 4'-phospho-N-pantothenoylcysteine (PPC). In the third step, PPC is decarboxylated to 4'-phosphopantetheine by phosphopantothenoylcysteine decarboxylase (CoaC). In the fourth step, 4'-phosphopantetheine is adenylylated to form dephospho-CoA by the enzyme phosphopantetheine adenylyl transferase (CoaD). Finally, dephospho-CoA is phosphorylated using ATP to coenzyme A by the enzyme dephosphocoenzyme A kinase (CoaE). Since coenzyme A is, in chemical terms, a thiol, it can react with carboxylic acids to form thioesters, thus functioning as an acyl group carrier. CoA assists in transferring fatty acids from the cytoplasm to the mitochondria. A molecule of coenzyme A carrying an acetyl group is also referred to as acetyl-CoA. When it is not attached to an acyl group, it is usually referred to as 'CoASH' or 'HSCoA'. Coenzyme A is also the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier proteins and formyltetrahydrofolate dehydrogenase. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production (Wikipedia).85-61-0C0001068161146900CO-A6557CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)[C@@H](O)C(=O)NCCC(=O)NCCSC21H36N7O16P3SInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1RGJOEKWQDUBAIZ-IBOSZNHHSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid767.534767.115208365-2.2210coenzyme A0-4FDB022614Acetoacetyl coenzyme a sodium salt;Coa;Coa hydrate;Coa-sh;Coash;Coenzyme a;Coenzyme a hydrate;Coenzyme a-sh;Coenzyme ash;Coenzymes a;Depot-zeel;Propionyl coa;Propionyl coenzyme a;S-propanoate;S-propanoate coa;S-propanoate coenzyme a;S-propanoic acid;S-propionate coa;S-propionate coenzyme a;Zeel;[(2r,3s,4r,5r)-5-(6-amino-9h-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatePW_C001099CoA21143868845387922892172407592414224595281329286231334211335118461810462958484214486554487965232102524710452801035477124573410857771016023155607516163841646817869301606961162697319970831887108163729319873472107458222822915190812269090224912417092151951301329915318249254884942616315769072937711913377222134772303297729211177550132775553347756311277633336776721297799611578047332780563507841333578567130792593337997433180005368806201188062737480635119806653769382838293834383986742881105553891105613901158423991158473981199514061201474051202313841203051221206344071207621171214061231214214331215211251216664291216824081217144141224044221227411201229041211229601351239654471239794681240791361242204641242654501249743751253414791255094781255794801255924841256342971260844811265494911265604821267463001268845011270462091271093911273012051275402061276673881281215081281335021283403953907LPA(18:2(9Z,12Z)/0:0)HMDB0007856LPA(18:2(9Z,12Z)/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. 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. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293).C006815099092362834ACYL-SN-GLYCEROL-3P24766514CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC(O)COP(O)(O)=OC21H39O7PInChI=1S/C21H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h6-7,9-10,20,22H,2-5,8,11-19H2,1H3,(H2,24,25,26)/b7-6-,10-9-ZQTAMPRZFOOEEP-HZJYTTRNSA-N{2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy}phosphonic acid434.51434.243340594-5.2432-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid0-2FDB0250491-(9z,12z-octadecadienoyl)-phosphatidic acid;1-linoleoyl-glycero-3-phosphate;Lpa(18:2);Lpa(18:2/0:0);Lpa(18:2n6/0:0);Lpa(18:2w6/0:0);Lysophosphatidic acid(18:2);Lysophosphatidic acid(18:2/0:0);Lysophosphatidic acid(18:2n6/0:0);Lysophosphatidic acid(18:2w6/0:0);1-(9z,12z-octadecadienoyl)-glycero-3-phosphate;1-linoleyl lysophosphatidic acid;1-linoleyl-2-lyso-sn-glycerol 3-phosphatidic acid;1-linoleylglycerol 3-phosphate;1-o-linoleyl-sn-glycerol 3-phosphate;Pa(18:2(9z,12z)/0:0);1-(9z,12z-octadecadienoyl)-glycero-3-phosphoric acidPW_C003907LPA18:225664222566549850763298507733194359249989163829891738310988828811397338911524339041149Docosahexaenoyl-CoAHMDB0062235Docosahexaenoyl-CoA, also known as dha-coa, belongs to the class of organic compounds known as very long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a very long aliphatic chain of 22 carbon atoms or more. Thus, docosahexaenoyl-CoA is considered to be a fatty ester lipid molecule. Docosahexaenoyl-CoA is considered to be a practically insoluble (in water) and relatively neutral molecule. Docosahexaenoyl-CoA can be biosynthesized from all-cis-docosa-4,7,10,13,16,19-hexaenoic acid. A long-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of docosahexaenoic acid.C161697067870565132CPD-17312CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=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=C2NC43H66N7O17P3SInChI=1S/C43H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h5-6,8-9,11-12,14-15,17-18,20-21,30-32,36-38,42,53-54H,4,7,10,13,16,19,22-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/b6-5-,9-8-,12-11-,15-14-,18-17-,21-20-/t32-,36-,37-,38+,42-/m1/s1MENFZXMQSYYVRK-CRCGJGBYSA-N(2R)-4-({[({[(2R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid1078.011077.344875861-4.199(2R)-4-[({[(2R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-[2-({2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid0-4(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-CoA;(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoyl-coenzyme A;DHA-CoA;docosahexaenoyl-coenzyme A;CoA(22:6(4Z,7Z,10Z,13Z,16Z,19Z));PW_C041149DHA-CoA2569649258952281895331874173299575238310118038212889339862388PA(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))HMDB0114970PA(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.C0041616337L-PHOSPHATIDATE[H][C@@](COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COP(O)(O)=O)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC43H69O8PInChI=1S/C43H69O8P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(45)51-41(40-50-52(46,47)48)39-49-42(44)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,32,34,41H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-40H2,1-2H3,(H2,46,47,48)/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t41-/m1/s1LMRGXWKSGCXJBV-CCMCUYBTSA-N[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid744.991744.47300618-6.862(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid0-21-linoleoyl-2-docosahexaenoyl-sn-glycero-3-phosphate ;1-linoleoyl-2-docosahexaenoyl-sn-phosphatidic acid ;PA(18:2/22:6) ;PA(18:2n6/22:6n3) ;PA(18:2w6/22:6w3) ;PA(40:8) ;Phosphatidic acid(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) ;Phosphatidic acid(18:2/22:6) ;Phosphatidic acid(18:2n6/22:6n3) ;Phosphatidic acid(18:2w6/22:6w3) ;Phosphatidic acid(40:8) ;Phosphatidate(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) ;Phosphatidate(18:2/22:6) ;Phosphatidate(18:2n6/22:6n3) ;Phosphatidate(18:2w6/22:6w3) ;Phosphatidate(40:8)PW_C062388PA40:8 345694940450224045117853393319465232994653134991793831041353821041363841420WaterHMDB0002111Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71% of Earth's surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the body's solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the sun's energy to split off water's hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the sun's energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia).7732-18-5C0000196215377937OH2OInChI=1S/H2O/h1H2XLYOFNOQVPJJNP-UHFFFAOYSA-Nwater18.015318.0105646861water00FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765133317DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0)HMDB0007266DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/0:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.C001659543899DIACYLGLYCEROL7822849[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC43H68O5InChI=1S/C43H68O5/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-43(46)48-41(39-44)40-47-42(45)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11-14,17-19,21-23,26,28,32,34,41,44H,3-4,6,8-10,15-16,20,24-25,27,29-31,33,35-40H2,1-2H3/b7-5-,13-11-,14-12-,19-17-,22-21-,23-18-,28-26-,34-32-/t41-/m0/s1GPMAAGRGFWBOSO-ULIJUFBVSA-N(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate664.997664.506675286-7.561diacylglycerol00FDB0244591-linoleoyl-2-docosahexaenoyl-sn-glycerol;Dag(18:2/22:6);Dag(18:2n6/22:6n3);Dag(18:2w6/22:6w3);Dag(40:8);Dg(18:2/22:6);Dg(18:2n6/22:6n3);Dg(18:2w6/22:6w3);Dg(40:8);Diacylglycerol;Diacylglycerol(18:2/22:6);Diacylglycerol(18:2n6/22:6n3);Diacylglycerol(18:2w6/22:6w3);Diacylglycerol(40:8);DiglyceridePW_C003317DG40:8174414985340331991803831181413981104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi244848814581818831298031763141767492500102729472737463129293166723636613851234249224475315031275158752079752161005317111535111253811035447120554312955731335605135562510856936584814358551465911147594115160401556100161629410764871786691101671411768421886889160716120571892067212211730619873892107402212743616374752228196225825822710118241101342571174813211761115117732131190417011927164120142811272829013263223348191742255304423503154243531843692322770182537719429377217134779403367796613078048332780573297824535378669331800223688927930893831383947963841105583901106403911132359411584539811620610911998240612006912212069940712105712412121612512126842912135212112140912312142338212185240512330411912362111812378613612383846412396844712398139912440537612494847212536247912544629712577448112595429912622147812659430012660429812672348412690450112741338812778320912816639512817751312831538933337TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z))HMDB0052816TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)) is a dilinoleic acid triglyceride. Triglycerides (TGs or TAGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position, one chain of docosahexaenoic acid at the C-2 position and one chain of linoleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)<br />TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.30778097[H]C(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC61H98O6InChI=1S/C61H98O6/c1-4-7-10-13-16-19-22-25-28-29-30-31-34-37-40-43-46-49-52-55-61(64)67-58(56-65-59(62)53-50-47-44-41-38-35-32-26-23-20-17-14-11-8-5-2)57-66-60(63)54-51-48-45-42-39-36-33-27-24-21-18-15-12-9-6-3/h7,10,16-21,25-28,30-33,37,40,46,49,58H,4-6,8-9,11-15,22-24,29,34-36,38-39,41-45,47-48,50-57H2,1-3H3/b10-7-,19-16-,20-17-,21-18-,28-25-,31-30-,32-26-,33-27-,40-37-,49-46-BXAFRFFCLQVNJP-AZAKSZIWSA-N1,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate927.449926.736340876-8.2601,3-bis[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate001-(9z,12z-octadecadienoyl)-2-(4z,7z,10z,13z,16z,19z-docosahexaenoyl)-3-(9z,12z-octadecadienoyl)-glycerol;1-linoleoyl-2-docosahexaenoyl-3-linoleoyl-glycerol;Tag(18:2/22:6/18:2);Tag(58:10);Tg(18:2/22:6/18:2);Tg(58:10);Tracylglycerol(18:2/22:6/18:2);Tracylglycerol(58:10);Triacylglycerol;TriglyceridePW_C033337TG58:103457049423MagnesiumHMDB0000547Magnesium salts are essential in nutrition, being required for the activity of many enzymes, especially those concerned with oxidative phosphorylation. Physiologically, it exists as an ion in the body. It is a component of both intra- and extracellular fluids and is excreted in the urine and feces. Deficiency causes irritability of the nervous system with tetany, vasodilatation, convulsions, tremors, depression, and psychotic behavior. Magnesium ion in large amounts is an ionic laxative, and magnesium sulfate (Epsom salts) is sometimes used for this purpose. So-called "milk of magnesia" is a water suspension of one of the few insoluble magnesium compounds, magnesium hydroxide; the undissolved particles give rise to its appearance and name. Milk of magnesia is a mild base, and is commonly used as an antacid.22537-22-0C003058881842013-HYDROXY-MAGNESIUM-PROTOPORP865DB01378[Mg++]MgInChI=1S/Mg/q+2JLVVSXFLKOJNIY-UHFFFAOYSA-Nmagnesium(2+) ion24.30523.9850418980magnesium(2+) ion22FDB003518Magnesium;Magnesium ions;Magnesium ion;Magnesium, doubly charged positive ion;Magnesium, ion (mg(2+));Mg(2+);Mg2+PW_C000423Mg2+86822742681647627272681158191888322936399833992211167461483491529431764142124102411592942233126293373745403147749148695449745652531045329111535611253761035906147593415160381556094161625016664841786594164688116069791997170205719420672272137233211725021473102167313198747322211763132118432101231222512324249125132881258122612729290152752851533730877137133772363297793733678393334784173357848911578522331785363567857413080020368800451848004837280623118806541358086515809652538184151938323839490027108596223110559390115687398119974406120070122120247382120702407120981408121181124121265429121319419121924125122086405122408422122759120122921399123307119123546374123835464123889455124477136124637376124978375125447297125598484125669479125777481125921482125947299125973495126000490126243478126553491126753300127125389127164501127380502127407388127451507127804209128125508128347395782Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmicP21695HMDBP00837GPD112q12-q13AC02515411.1.1.81044814762783Glycerol-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.
HMDBP00838GPAM10q25.2AL39198612.3.1.151646320871021355846282214691-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.
HMDBP01581AGPAT16p21.3CR81247812.3.1.51148149149542210810214158334311335218462125450Phosphatidate phosphatase LPIN1Q14693Plays important roles in controlling the metabolism of fatty acids at differents levels. Acts as a magnesium-dependent phosphatidate phosphatase enzyme which catalyzes the conversion of phosphatidic acid to diacylglycerol during triglyceride, phosphatidylcholine and phosphatidylethanolamine biosynthesis in the reticulum endoplasmic membrane. Acts also as a nuclear transcriptional coactivator for PPARGC1A/PPARA to modulate lipid metabolism gene expression (By similarity). Is involved in adipocyte differentiation. May also be involved in mitochondrial fission by converting phosphatidic acid to diacylglycerol (By similarity).
HMDBP11805LPIN12p25.1D8001013.1.3.42548949110572390237Diacylglycerol O-acyltransferase 1O75907Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. In liver, plays a role in esterifying exogenous fatty acids to glycerol. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders.
HMDBP00243DGAT18q24.3CH47116212.3.1.20; 2.3.1.76320522549049293Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic1PW_P0002933127822240325664Glycerol-3-phosphate acyltransferase1PW_P00566413138783238672256651-Acyl-sn-glycerol-3-phosphate acyltransferase1PW_P00566513139146924042495666Phosphatidate phosphatase1PW_P00566613136545074242324196495667Diacylglycerol O-acyltransferase1PW_P00566713137237244264955814PW_R055814Right18217411441Compoundtrue182175400341Compoundtrue18217611341Compoundfalse1821777211Compoundtrue182178811Compoundfalse4593929355999PW_R055999Right1829158391Compoundfalse182916811Compoundfalse18291710991Compoundfalse18291839071Compoundfalse46124566465286PW_R065286Right22006339071Compoundfalse220064411491Compoundfalse22006510991Compoundfalse220066623881Compoundfalse55411566565287PW_R065287Right220067623881Compoundfalse22006814201Compoundfalse22006933171Compoundfalse22007011041Compoundfalse55412566665288PW_R065288Right22007133171Compoundfalse2200728391Compoundfalse220073333371Compoundfalse22007410991Compoundfalse5541356676621631144260false84636710regular503066216440034255false82724210regular7878662165113423false74644010regular100110662166721259false114636610regular50306621678123false119644110regular100110662168839223false124629110regular10010066216910992285false159632810regular503066217010994985false391113310regular503066217110994985false1301112810regular50306621723907223false164644310regular1001006621733907493false164694510regular10010066217441149493false1596109510regular10011066217562388493false119694810regular10010066217614204949false1142110510regular78786621773317493false74694810regular10010066217811044946false854112310regular4443662179839493false696109310regular10010066218033337493false29694810regular10010031946578226false9464568proteinregular160803194667832299false14015618proteinregular1507031946714694999false13968658proteinregular1507031946854504999false9468618proteinregular1507031946923749119false4968568proteinregular1608021168729325041231864131946521168856642504122318642319466211689566525041493186433194672116905666250414931864431946821169156672504149318645319469963877M1746 493 C1776 493 1819 493 1847 493 C1847 522 1845 969 1845 995 C1820 994 1769 995 1746 995 83false18trueM 1812.6189391138873 1042.890599551138 L 1800 1051 L 1813.3324163551192 1057.8736216170046false963878M896 382 C895 440 916 496 946 496 5false18963879M905 281 C906 347 916 496 946 496 5false18963880M846 495 C876 495 916 496 946 496 5false18963881M746 495 C716 495 621 493 591 493 5false18trueM 787.0096189432334 560.5 L 800 553 L 787.0096189432334 545.5false963882M1146 381 C1147 447 1136 496 1106 496 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false963883M1196 496 C1166 496 1136 496 1106 496 5false18trueM 25.946855044164835 13.26155629629604 L 11 12 L 17.380887721185843 25.575134323078345false963884M1346 341 C1348 425 1371 596 1401 596 5false18963885M1296 496 C1317 497 1325 497 1348 497 C1348 521 1348 574 1348 597 C1371 597 1380 596 1401 596 5false18trueM 1389.0096189432334 554.5 L 1402 547 L 1389.0096189432334 539.5false963886M1596 343 C1598 418 1581 596 1551 596 5false18trueM 770.9468550441649 158.26155629629605 L 756 157 L 762.3808877211858 170.57513432307834false963887M1646 493 C1616 493 1620 493 1598 493 C1598 516 1597 570 1598 596 C1572 596 1576 596 1551 596 5false18trueM 770.9468550441649 158.26155629629605 L 756 157 L 762.3808877211858 170.57513432307834false963888M1646 995 C1616 995 1620 995 1598 995 C1598 973 1597 920 1597 899 C1576 899 1567 899 1546 900 5false18trueM 1559.6189391138873 842.8905995511379 L 1547 851 L 1560.3324163551192 857.8736216170046false963889M1596 1145 C1594 1057 1576 900 1546 900 5false18963890M1351 1143 C1349 1077 1366 900 1396 900 5false18trueM 1130.9468550441647 598.261556296296 L 1116 597 L 1122.380887721186 610.5751343230784false963891M1296 998 C1326 998 1329 998 1348 998 C1348 979 1346 920 1346 900 C1366 900 1376 900 1396 900 5false18trueM 1130.9468550441647 598.261556296296 L 1116 597 L 1122.380887721186 610.5751343230784false963892M1196 998 C1182 998 1171 998 1148 999 C1148 976 1147 920 1147 895 C1125 895 1120 896 1096 896 5false18trueM 1109.9903810567666 839.5 L 1097 847 L 1109.9903810567666 854.5false963893M1142 1144 C1140 1067 1126 896 1096 896 5false18963894M846 998 C876 998 872 998 896 998 C896 974 897 919 897 896 C918 896 925 896 946 896 5false18trueM 530.9468550441649 558.261556296296 L 516 557 L 522.3808877211858 570.5751343230784false963895M898 1144.5 C899 1055.5 916 896 946 896 5false18trueM 530.9468550441649 558.261556296296 L 516 557 L 522.3808877211858 570.5751343230784false963896M746 998 C716 998 720 998 698 998 C698 977 697 917 697 895 C676 895 679 897 656 896 5false18trueM 670.3038993762138 840.0713449077346 L 657 847 L 669.6523410120692 855.0571872830604false963897M696 1143 C698 1092 686 896 656 896 5false18963898M396 998 C418 997 425 999 447 999 C447 977 447 921 448 897 C471 897 474 896 496 896 5false18trueM 271.94685504416486 558.261556296296 L 257 557 L 263.38088772118584 570.5751343230784false963899M441 1148 C441 1088 466 896 496 896 5false18trueM 271.94685504416486 558.261556296296 L 257 557 L 263.38088772118584 570.5751343230784false2231952504155814859748662163963878Left859749662164963879Left859750662165963880Left859751662166963882Right859752662167963883Right182263459392116872231962504155999859753662168963884Left859754662167963885Left859755662169963886Right859756662172963887Right182264459402116882231972504165286859757662173963888Left859758662174963889Left859759662171963890Right859760662175963891Right182265459412116892231982504165287859761662175963892Left859762662176963893Left859763662177963894Right859764662178963895Right182266459422116902231992504165288859765662177963896Left859766662179963897Left859767662180963898Right859768662170963899Right1822674594321169115320159612504114false44145816regular13532662165963881Right177919638772213139236030.40.40214902402213143027590.60.6-90232803602213152002100.80.8021432726793216M1155.6666870117188 595 C1208.6666870117188 594 1681.6666870117188 596 1745.6666870117188 595 84false60.00.093217M247 899 C308 899 1694 900 1745 899 91false61498.00.093218M125 225 C125 175 175 125 225 125 C725 125 1376 125 1876 125 C1926 125 1976 175 1976 225 C1976 528 1976 921 1976 1224 C1976 1274 1926 1324 1876 1324 C1376 1324 725 1324 225 1324 C175 1324 125 1274 125 1224 C125 921 125 528 125 225 1true61851.01199.047677515Mitochondria Outer Membrane1162553201.01.01601547677615Endoplasmic Reticulum Membrane248854201.01.01601547677715Cytosol1732175201.01.01601520336910446031156567174869039#FFEBEB459212320337039368024779417479234#FFEEDE41500129