3390PathwayCardiolipin Biosynthesis CL(10:0/10:0/18:1(11Z)/22:1(11Z))The biosynthesis of cardiolipin (CL) begins in the endoplasmic reticulum. Glycerone phosphate interacts with an NADPH resulting in the release of NADP and glycerol 3-phosphate. Glycerol 3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LysoPA). The resulting compound reacts with an acyl-CoA via lysophosphatidate acyltransferase, resulting in the release of a phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate). Phosphatidic acid is transported to the mitochondrial outer membrane. Once in, it gets transported into the mitochondrial inner membrane. The phosphatidic acid reacts with cytidine triphosphate through a phosphatidate cytidyltransferase resulting in the release of a CDP-diacylglycerol (CDP-DG). The resulting compound reacts with a glycerol 3-phosphate through a CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase resulting in the release of cytidine monophosphate and phosphatidylglycerophosphate (PGP). PGP reacts with phosphatidylglycerophosphatase GEP4 resulting in the release of phosphatidylglycerol (PG). PG reacts with a CDP-DG through a cardiolipin synthase resulting in the release of CL and cytidine monophosphate. Cardiolipin remodelling begins with the removal of an acyl chain to form 1-monolysocardiolipin (1-MLCL) via the lipase Cld1p. This is followed by the enzyme Taz1p transferring an acyl chain from a phospholipid (e.g. phosphatidylcholine) to reform cardiolipin.MetabolicPW003596CenterPathwayVisualizationContext388128502050#000099PathwayVisualization33523390Cardiolipin Biosynthesis CL(10:0/10:0/18:1(11Z)/22:1(11Z))The biosynthesis of cardiolipin (CL) begins in the endoplasmic reticulum. Glycerone phosphate interacts with an NADPH resulting in the release of NADP and glycerol 3-phosphate. Glycerol 3-phosphate reacts with glycerol-3-phosphate O-acyltransferase resulting in the release of 1-acyl-sn-glycerol 3-phosphate (lysophosphatidic acid or LysoPA). The resulting compound reacts with an acyl-CoA via lysophosphatidate acyltransferase, resulting in the release of a phosphatidic acid (PA or 1,2-diacyl-sn-glycerol 3-phosphate). Phosphatidic acid is transported to the mitochondrial outer membrane. Once in, it gets transported into the mitochondrial inner membrane. The phosphatidic acid reacts with cytidine triphosphate through a phosphatidate cytidyltransferase resulting in the release of a CDP-diacylglycerol (CDP-DG). The resulting compound reacts with a glycerol 3-phosphate through a CDP-diacylglycerol-glycerol-3-phosphate 3-phosphatidyltransferase resulting in the release of cytidine monophosphate and phosphatidylglycerophosphate (PGP). PGP reacts with phosphatidylglycerophosphatase GEP4 resulting in the release of phosphatidylglycerol (PG). PG reacts with a CDP-DG through a cardiolipin synthase resulting in the release of CL and cytidine monophosphate. Cardiolipin remodelling begins with the removal of an acyl chain to form 1-monolysocardiolipin (1-MLCL) via the lipase Cld1p. This is followed by the enzyme Taz1p transferring an acyl chain from a phospholipid (e.g. phosphatidylcholine) to reform cardiolipin.Metabolic181CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle6Caenorhabditis elegans6239EukaryoteRoundworm17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia425Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel51Picea sitchensis3332EukaryoteSitka spruce29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast5CytoplasmGO:00057371CytosolGO:00058294PeroxisomeGO:000577724Mitochondrial Intermembrane SpaceGO:00057583Mitochondrial MatrixGO:00057592MitochondrionGO:00057397Endoplasmic Reticulum MembraneGO:000578912Mitochondrial Inner MembraneGO:00057436LysosomeGO:000576413Endoplasmic ReticulumGO:000578316Lysosomal LumenGO:004320235ChloroplastGO:000950711Extracellular SpaceGO:000561514Mitochondrial Outer MembraneGO:000574131Periplasmic SpaceGO:000562010Cell MembraneGO:000588636MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032532Inner MembraneGO:007025825Golgi apparatusGO:000579427Peroxisome MembraneGO:00057788Smooth Endoplasmic Reticulum GO:000579015NucleusGO:000563426Golgi apparatus membraneGO:000013918Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520240PeriplasmGO:004259719sarcoplasmic reticulumGO:00165291LiverBTO:000075972928StomachBTO:0001307155268Blood VesselBTO:000110274114Adrenal MedullaBTO:000004971825IntestineBTO:00006487Nervous 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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_C001134Dhapp10268147423305542534258131085908147593615168841604266031577098132779341117837434578559334938241241105513881158391181207331221225644181225904081233331351251374541251623741257872971259502991267124891267364821272422051283035061283305021144NADHHMDB0001487NADH 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+21546708753157883184831116214632614645422314927801742502242544245471045761846947052411035327111535311256261085639107569910057201055742117596314760371556070157609316161301596232166648317866011526692101684318869101877100163716820571912067453219745422074722227525213753221075582127572160759017081952258218151824322684131628420224913919591552491191516412015281121812851224628612266287125212271325722313325294153303084232931542354318424013224240531242454320769122937713613377210134773723317780411477955132779903277799134778379345799291308001936880387310803883048072211993823124948233831105503881128559411328039011553739811553911811585633611620510911997340612019340712054912212059340912117042412117142512256941812261538412268712512275812012318313512321813712374245912374346012514145412518812112527313612535947912555048112573048312573629712580929912651749512671748912676648012682330012690250112721320812830850612836139112843039581Glycerol 3-phosphateHMDB0000126Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).17989-41-2C0009343916215978GLYCEROL-3P388308DB02515OC[C@@H](O)COP(O)(O)=OC3H9O6PInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1AWUCVROLDVIAJX-GSVOUGTGSA-N[(2R)-2,3-dihydroxypropoxy]phosphonic acid172.0737172.013674532-0.7543-phosphoglycerol0-2FDB0218001-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acidPW_C000081Glyc1P1043814752148842211558629510762961088412162912217010653188125461511255022315319249348141742466318424673157803011178052350783723457837813279952134818082539382612494789384110553388110636391115840118120756122121297418121345121121415433123353135123867454123974468125788297125978489125991299127243205127431506721NADHMDB0000902NAD (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_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283952742Decanoyl-CoAHMDB0006404Decanoyl CoA is a human liver acyl-CoA ester. It is selected to determine apparent kinetic constants for human liver acyl-CoA due to its relevance to the human diseases with cellular accumulation of this esters, especially to metabolic defects in the acyl-CoA dehydrogenation steps of the branched-chain amino acids, lysine, 5-hydroxy lysine, tryptophan, and fatty acid oxidation pathways. It is concluded that the substrate concentration is decisive for the glycine conjugate formation and that the occurrence in urine of acylglycines reflects an intramitochondrial accumulation of the corresponding acyl-CoA ester. (PMID: 3707752).1264-57-9C0527444061528493389510CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC31H54N7O17P3SInChI=1S/C31H54N7O17P3S/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38/h18-20,24-26,30,41-42H,4-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46)/t20-,24-,25-,26?,30-/m1/s1CNKJPHSEFDPYDB-BOJFXZHGSA-N{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(decanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid921.783921.250973563-2.509decanoyl-coa0-4FDB023910Decanoyl coenzyme a monohydrate;Decanoyl-coa;Decanoyl-coenzyme a;S-decanoate;S-decanoate coenzyme a;S-decanoic acid;CoA(10:0)PW_C002742Decanoy863391645289103698716171171632549622254994977243133778811121202554061206494071229291201232661191256064791271335011099Coenzyme 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_C001099CoA211438688453879228921724075924142245952813292862313342113351184618104629584842144865544879652321025247104528010354771245734108577710160231556075161638416468178693016069611626973199708318871081637293198734721074582228229151908122690902249124170921519513013299153182492548849426163157690729377119133772221347723032977292111775501327755533477563112776333367767212977996115780473327805635078413335785671307925933379974331800053688062011880627374806351198066537693828382938343839867428811055538911056139011584239911584739811995140612014740512023138412030512212063440712076211712140612312142143312152112512166642912168240812171441412240442212274112012290412112296013512396544712397946812407913612422046412426545012497437512534147912550947812557948012559248412563429712608448112654949112656048212674630012688450112704620912710939112730120512754020612766738812812150812813350212834039555362LysoPA(10:0/0:0)LPA(10:0/0:0) 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(10:0/0:0), in particular, consists of one decanoyl 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.C0068116975ACYL-SN-GLYCEROL-3PCCCCCCCCCC(=O)OCC(O)COP(O)(O)=OC13H27O7PInChI=1S/C13H27O7P/c1-2-3-4-5-6-7-8-9-13(15)19-10-12(14)11-20-21(16,17)18/h12,14H,2-11H2,1H3,(H2,16,17,18)CMQAWGIRCVKCMC-UHFFFAOYSA-N[3-(decanoyloxy)-2-hydroxypropoxy]phosphonic acid326.326326.149440207-2.6633-(decanoyloxy)-2-hydroxypropoxyphosphonic acid0-21-decanoyl-glycero-3-phosphate ;1-decanoyl-lysophosphatidic acid ;LPA(10:0) ;Lysophosphatidic acid(10:0/0:0) ;Lysophosphatidic acid(10:0)PW_C055362LPA(10:106631702549722254984955512PA(10:0/10:0)PA(10:0/10:0)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(10:0/10:0), in particular, consists of two decanoyl 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.C0041616337L-PHOSPHATIDATE[H][C@@](COC(=O)CCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCC23H45O8PInChI=1S/C23H45O8P/c1-3-5-7-9-11-13-15-17-22(24)29-19-21(20-30-32(26,27)28)31-23(25)18-16-14-12-10-8-6-4-2/h21H,3-20H2,1-2H3,(H2,26,27,28)/t21-/m1/s1PHQFPHNJHDEXLJ-OAQYLSRUSA-N[(2R)-2,3-bis(decanoyloxy)propoxy]phosphonic acid480.579480.285205407-5.532(2R)-2,3-bis(decanoyloxy)propoxyphosphonic acid0-21-caproyl-2-caproyl-sn-glycero-3-phosphate ;1-caproyl-2-caproyl-sn-phosphatidic acid ;PA(20:0) ;Phosphatidic acid(10:0/10:0) ;Phosphatidic acid(20:0) ;Phosphatidate(10:0/10:0) ;Phosphatidate(20:0)PW_C055512PA20:0 101491891015119710657188255004957Cytidine triphosphateHMDB0000082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C000057CTP42723115082718257661015800108707718875931609137195914221312194164125102881528515115317249153422215374183475917426503157731512878448111787331327994913479957130799643298041617094784384948121259481738298677223110633391113268395113273389115525136115530399120328410120854122121340121122212124122983444123434135124764118125654485125840297126374299127292205127935388170PyrophosphateHMDB0000250The anion, the salts, and the esters of pyrophosphoric acid are called pyrophosphates. The pyrophosphate anion is abbreviated PPi and is formed by the hydrolysis of ATP into AMP in cells. This hydrolysis is called pyrophosphorolysis. The pyrophosphate anion has the structure P2O74-, and is an acid anhydride of phosphate. It is unstable in aqueous solution and rapidly hydrolyzes into inorganic phosphate. Pyrophosphate is an osteotoxin (arrests bone development) and an arthritogen (promotes arthritis). It is also a metabotoxin (an endogenously produced metabolite that causes adverse health affects at chronically high levels). Chronically high levels of pyrophosphate are associated with hypophosphatasia. Hypophosphatasia (also called deficiency of alkaline phosphatase or phosphoethanolaminuria) is a rare, and sometimes fatal, metabolic bone disease. Hypophosphatasia is associated with a molecular defect in the gene encoding tissue non-specific alkaline phosphatase (TNSALP). TNSALP is an enzyme that is tethered to the outer surface of osteoblasts and chondrocytes. TNSALP hydrolyzes several substances, including inorganic pyrophosphate (PPi) and pyridoxal 5'-phosphate (PLP), a major form of vitamin B6. When TSNALP is low, inorganic pyrophosphate (PPi) accumulates outside of cells and inhibits the formation of hydroxyapatite, one of the main components of bone, causing rickets in infants and children and osteomalacia (soft bones) in adults. Vitamin B6 must be dephosphorylated by TNSALP before it can cross the cell membrane. Vitamin B6 deficiency in the brain impairs synthesis of neurotransmitters which can cause seizures. In some cases, a build-up of calcium pyrophosphate dihydrate crystals in the joints can cause pseudogout.14000-31-8C0001364410218361PPI559142DB04160[O-]P([O-])(=O)OP([O-])([O-])=OO7P2InChI=1S/H4O7P2/c1-8(2,3)7-9(4,5)6/h(H2,1,2,3)(H2,4,5,6)/p-4XPPKVPWEQAFLFU-UHFFFAOYSA-J(phosphonooxy)phosphonic acid173.9433173.9119253784pyrophosphoric acid0-3FDB021918(4-)diphosphoric acid ion;(p2o74-)diphosphate;Diphosphate;Diphosphoric acid;Ppi;Pyrometaphosphate;Pyrophosphate;Pyrophosphate tetraanion;Pyrophosphate(4-) ion;[o3popo3](4-);Diphosphat;P2o7(4-);Pyrophosphat;Pyrophosphate ion;Phosphonato phosphoric acid;Pyrophosphoric acid;Pyrophosphoric acid ionPW_C000170Ppi12235463842923735328822212173162049241059281529417514486854503489525210452941015409117542410354331185458120554811155591325584133560613556551085879107623916669781997073188713416372721607312198731821382751518283210118691611200222212041164123152251232324912512288125792261269529015219306153751834760174256131542697318772353297731712877635336784163357892833179153112799501347995813080047372804171708563019478638494814125948193829867822311063439111327039511327538911552713611553239911993412212001712412003240612033041012093640712126142912134112112148638312240742212298544412350211912383146412404439812497737512532429712539529912541047912559748412565648512587648112655249112686920512693538812695050112733720612812450842684CDP-DG(10:0/10:0)CDP-DG(10:0/10:0) 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(10:0/10:0), in particular, consists of two decanoyl 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(10:0/10:0) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.C0026917962CDPDIACYLGLYCEROL[H][C@@](COC(=O)CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCC32H57N3O15P2InChI=1S/C32H57N3O15P2/c1-3-5-7-9-11-13-15-17-27(36)45-21-24(48-28(37)18-16-14-12-10-8-6-4-2)22-46-51(41,42)50-52(43,44)47-23-25-29(38)30(39)31(49-25)35-20-19-26(33)34-32(35)40/h19-20,24-25,29-31,38-39H,3-18,21-23H2,1-2H3,(H,41,42)(H,43,44)(H2,33,34,40)/t24-,25-,29+,30?,31-/m1/s1YLSRMBDSMCQRPS-TXNQHKHTSA-N{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis(decanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid785.762785.326492143-3.295[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis(decanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid0-21,2-didecanoyl-rac-glycero-3-cdp;1,2-didecanoyl-rac-glycero-3-cytidine-5'-diphosphate;Cdp-dg(20:0);Cdp-diacylglycerol(10:0/10:0);Cdp-diacylglycerol(20:0)PW_C042684CDP-DG(43864PGP(10:0/10:0)PGP(10:0/10:0) is a phosphatidylglycerophosphate (PGP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site followed by another phosphate moiety. Phosphatidylglycerolphosphate is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant (up to 11% of the total). It is well established that the concentration of phosphatidylglycerolphosphate increases during fetal development. Phosphatidylglycerolphosphate may be present in animal tissues merely as a precursor for cardiolipin synthesis. 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. Fatty acids containing 16, 18 and 20 carbons are the most common. PGP(10:0/10:0), in particular, consists of one chain of capric acid at the C-1 position and one chain of capric acid at the C-2 position. They are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to phosphatidylglycerols (PGs). 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.C0389237393L-1-PHOSPHATIDYL-GLYCEROL-P[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCC26H52O13P2InChI=1S/C26H52O13P2/c1-3-5-7-9-11-13-15-17-25(28)35-21-24(39-26(29)18-16-14-12-10-8-6-4-2)22-38-41(33,34)37-20-23(27)19-36-40(30,31)32/h23-24,27H,3-22H2,1-2H3,(H,33,34)(H2,30,31,32)/t23-,24+/m0/s1GWYHIFXNUFBOBE-BJKOFHAPSA-N[(2S)-3-({[(2R)-2,3-bis(decanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid634.637634.28831573-4.194(2S)-3-{[(2R)-2,3-bis(decanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid0-31-decanoyl-2-decanoyl-sn-glycero-3-phospho-(1'-sn-glycerol-3'-phosphate) ;PGP(20:0)PW_C043864PGP20:064Cytidine monophosphateHMDB0000095Cytidine monophosphate, also known as 5'-cytidylic acid and abbreviated CMP, is a nucleotide. It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine. Cytidine monophosphate (CMP) is derived from cytidine triphosphate (CTP) with subsequent loss of two phosphates. The synthesis of the pyrimidines CTP and UTP occurs in the cytoplasm and starts with the formation of carbamoyl phosphate from glutamine and CO2. Next, aspartate undergoes a condensation reaction with carbamoyl-phosphate to form orotic acid. In a subsequent cyclization reaction, the enzyme Aspartate carbamoyltransferase forms N-carbamoyl-aspartate which is converted into dihydroorotic acid by Dihydroorotase. The latter is converted to orotate by Dihydroorotate oxidase. Orotate is covalently linked with a phosphorylated ribosyl unit with Orotate phosphoribosyltransferase (aka "PRPP transferase") catalyzing reaction, yielding orotidine monophosphate (OMP). Orotidine-5-phosphate is decarboxylated by Orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). UMP is phosphorylated by two kinases to uridine triphosphate (UTP) via two sequential reactions with ATP. CTP is subsequently formed by amination of UTP by the catalytic activity of CTP synthetase. Cytosine monophosphate (CMP) and uridine monophosphate (UMP) have been prescribed for the treatment of neuromuscular affections in humans. Patients treated with CMP/UMP recover from altered neurological functions. Additionally, the administration of CMP/UMP appears to favour the entry of glucose in the muscle and CMP/UMP may be important in maintaining the level of hepatic glycogen constant during exercise. [PMID:18663991].63-37-6C00055613117361CMP5901NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1OC9H14N3O8PInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1IERHLVCPSMICTF-XVFCMESISA-N{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid323.1965323.051850951-1.305cytidine monophosphate0-2FDB0118825'-cmp;5-cytidylate;5-cytidylic acid;Cmp;Cytidine 5'-monophosphate;Cytidine 5'-monophosphorate;Cytidine 5'-monophosphoric acid;Cytidine 5'-phosphate;Cytidine 5'-phosphorate;Cytidine 5'-phosphoric acid;Cytidine mono(dihydrogen phosphate);Cytidine monophosphate;Cytidylate;Cytidylic acid;Cytidine-5'-monophosphate;Pc;Cytidine-5'-monophosphoric acidPW_C000064CMP11518251214273423386184972565768101580210870791887595160914724991512249257195121961641221015115274285153363081537349348151742652315784491117848811578573130787361327995313479969331804211709479138494821383986802231106373911132773901155353981208551221213461211222161241224874051226051251234351351247681181250533761251771361258412971263782991266414781267523001272932051279403881282172091283463951420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131104PhosphateHMDB0001429Phosphate 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_C001104Pi244848814581818831298031763141767492500102729472737463129293166723636613851234249224475315031275158752079752161005317111535111253811035447120554312955731335605135562510856936584814358551465911147594115160401556100161629410764871786691101671411768421886889160716120571892067212211730619873892107402212743616374752228196225825822710118241101342571174813211761115117732131190417011927164120142811272829013263223348191742255304423503154243531843692322770182537719429377217134779403367796613078048332780573297824535378669331800223688927930893831383947963841105583901106403911132359411584539811620610911998240612006912212069940712105712412121612512126842912135212112140912312142338212185240512330411912362111812378613612383846412396844712398139912440537612494847212536247912544629712577448112595429912622147812659430012660429812672348412690450112741338812778320912816639512817751312831538943853PG(10:0/10:0)PG(10:0/10:0) is a phosphatidylglycerol - a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(10:0/10:0), in particular, consists of one chain of capric acid at the C-1 position and one chain of capric acid at the C-2 position. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant (up to 11% of the total). It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for cardiolipin synthesis. C0034417517L-1-PHOSPHATIDYL-GLYCEROL[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCC26H51O10PInChI=1S/C26H51O10P/c1-3-5-7-9-11-13-15-17-25(29)33-21-24(22-35-37(31,32)34-20-23(28)19-27)36-26(30)18-16-14-12-10-8-6-4-2/h23-24,27-28H,3-22H2,1-2H3,(H,31,32)/t23-,24+/m0/s1IOLZSQRFJBMYSU-BJKOFHAPSA-N[(2R)-2,3-bis(decanoyloxy)propoxy][(2S)-2,3-dihydroxypropoxy]phosphinic acid554.658554.32198484-5.593(2R)-2,3-bis(decanoyloxy)propoxy((2S)-2,3-dihydroxypropoxy)phosphinic acid0-11-decanoyl-2-decanoyl-sn-glycero-3-phospho-(1'-glycerol);1-decanoyl-2-decanoyl-sn-glycero-3-phosphoglycerol;PG(10:0/10:0);PG(20:0);Phosphatidylglycerol(10:0/10:0);Phosphatidylglycerol(20:0)PW_C043853PG108248CDP-DG(18:1(11Z)/22:1(11Z))CDP-DG(18:1(11Z)/22:1(11Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol (CDP-DG). CDP-diacylglycerol is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols 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. CDP-DG(18:1(11Z)/22:1(11Z)), in particular, consists of one chain of cis-vaccenic acid at the C-1 position and one chain of (11Z)-docosenoic acid at the C-2 position. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts (perhaps only 0.05% or so of the total phospholipids).C0026917962CDPDIACYLGLYCEROL[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC\C=C/CCCCCCCCCCC52H93N3O15P2InChI=1S/C52H93N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h14,16,20-21,39-40,44-45,49-51,58-59H,3-13,15,17-19,22-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b16-14-,21-20-/t44-,45-,49-,50-,51-/m1/s1KCKRYGWALAZSMM-KJFOMNFOSA-N1062.271061.608193303-5.93CDP-DG(18:1(11Z)/22:1(11Z));CDP-Diacylglycerol(18:1(11Z)/22:1(11Z));1-cis-Vaccenoyl-2-(11Z-docosenoyl)-sn-glycero-3-CDP;1-cis-Vaccenoyl-2-(11Z-docosenoyl)-sn-glycero-3-cytidine-5'-diphosphate;CDP-DG(18:1/22:1);CDP-Diacylglycerol(18:1/22:1);CDP-DG(18:1n7/22:1n13);CDP-Diacylglycerol(18:1n7/22:1n13);CDP-DG(18:1w7/22:1w13);CDP-Diacylglycerol(18:1w7/22:1w13);CDP-DG(40:2);CDP-Diacylglycerol(40:2)PW_C10824845943CL(10:0/10:0/18:1(11Z)/22:1(11Z))CL(10:0/10:0/18:1(11Z)/22:1(11Z)) is a cardiolipin (CL). Cardiolipins are sometimes called a 'double' phospholipid because they have four fatty acid tails, instead of the usual two. CL(10:0/10:0/18:1(11Z)/22:1(11Z)) contains two chains of decanoic acid at the C1 and C2 positions, one chain of (11Z-octadecenoyl) at the C3 position, one chain of (11Z-docosenoyl) at the C4 position. 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.C0598028494CARDIOLIPIN[H][C@](O)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCCCCCC69H130O17P2InChI=1S/C69H130O17P2/c1-5-9-13-17-21-23-25-27-29-30-31-32-34-36-38-40-44-48-52-56-69(74)86-65(60-80-67(72)54-50-46-43-39-37-35-33-28-26-24-22-18-14-10-6-2)62-84-88(77,78)82-58-63(70)57-81-87(75,76)83-61-64(85-68(73)55-51-47-42-20-16-12-8-4)59-79-66(71)53-49-45-41-19-15-11-7-3/h24,26,30-31,63-65,70H,5-23,25,27-29,32-62H2,1-4H3,(H,75,76)(H,77,78)/b26-24-,31-30-/t63-,64+,65+/m0/s1IRJUQMXZAIFVBV-VPGNIRNUSA-N[(2S)-3-({[(2R)-2,3-bis(decanoyloxy)propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy][(2R)-2-[(11Z)-docos-11-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid1293.731292.878326722-7.163(2S)-3-{[(2R)-2,3-bis(decanoyloxy)propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxy((2R)-2-[(11Z)-docos-11-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy)phosphinic acid0-2PW_C045943CL105227MLCL(0:0/10:0/18:1(11Z)/22:1(11Z))MLCL(0:0/10:0/18:1(11Z)/22:1(11Z)) is a monolysocardiolipin (MLCL). MLCL is a phospholipid with three fatty acid chains that is located in the inner mitochondrial membrane (IMM). As part of cardiolipin remodelling, one acyl chain is removed by a lipase enzyme to generate MLCL. Enzymes such as tafazzin, monolysocardiolipin acyltransferase, or lysocardiolipin acyltransferase transfer a fourth fatty acid chain to MLCL to reform cardiolipin. MLCL(0:0/10:0/18:1(11Z)/22:1(11Z)), in particular, consists of one chain of capric acid at the C-2 position, one chain of cis-vaccenic acid at the C-3 position, and one chain of (11Z)-docosenoic acid at the C-4 position.[H][C@@](CO)(COP(O)(=O)OC[C@@H](O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\C=C/CCCCCCCCCC)OC(=O)CCCCCCCCCC59H112O16P2InChI=1S/C59H112O16P2/c1-4-7-10-13-16-18-20-22-24-25-26-27-29-31-33-35-38-41-44-47-59(64)75-56(51-69-57(62)45-42-39-37-34-32-30-28-23-21-19-17-14-11-8-5-2)53-73-77(67,68)71-50-54(61)49-70-76(65,66)72-52-55(48-60)74-58(63)46-43-40-36-15-12-9-6-3/h19,21,25-26,54-56,60-61H,4-18,20,22-24,27-53H2,1-3H3,(H,65,66)(H,67,68)/b21-19-,26-25-/t54-,55-,56-/m1/s1AHFSYULARGZBDY-PZHOLFOWSA-N1139.4771138.742561522MLCL(0:0/10:0/18:1(11Z)/22:1(11Z));Monolysocardiolipin(0:0/10:0/18:1(11Z)/22:1(11Z));MLCL(0:0/10:0/18:1/22:1);Monolysocardiolipin(0:0/10:0/18:1/22:1);MLCL(0:0/10:0/18:1n7/22:1n13);Monolysocardiolipin(0:0/10:0/18:1n7/22:1n13);MLCL(0:0/10:0/18:1w7/22:1w13);Monolysocardiolipin(0:0/10:0/18:1w7/22:1w13);MLCL(50:2);Monolysocardiolipin(50:2);1-Monolysocardiolipin;1-MLCLPW_C10522755665PC(10:0/10:0)PC(10:0/10:0) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(10:0/10:0), in particular, consists of two decanoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.[H][C@@](COC(=O)CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCC28H56NO8PInChI=1S/C28H56NO8P/c1-6-8-10-12-14-16-18-20-27(30)34-24-26(25-36-38(32,33)35-23-22-29(3,4)5)37-28(31)21-19-17-15-13-11-9-7-2/h26H,6-25H2,1-5H3/t26-/m1/s1MLKLDGSYMHFAOC-AREMUKBSSA-N(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium565.729565.374354765-6.400(2-{[(2R)-2,3-bis(decanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium00PW_C055665PC93981639432195108327LysoPC(10:0/0:0)LysoPC(10:0/0:0) is a lysophosphatidylcholine, which is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2 as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPC(10:0/0:0), in particular, consists of one chain of capric acid at the C-1 position.C04230 PHOSPHATIDYLCHOLINE[H][C@@](O)(COC(=O)CCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)CC18H38NO7PInChI=1S/C18H38NO7P/c1-5-6-7-8-9-10-11-12-18(21)24-15-17(20)16-26-27(22,23)25-14-13-19(2,3)4/h17,20H,5-16H2,1-4H3/t17-/m1/s1SECPDKKEUKDCPG-QGZVFWFLSA-N(2-{[(2R)-3-(decanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium411.476411.238589566-4.801(2-{[(2R)-3-(decanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium00LysoPC(10:0/0:0);LPC(10:0/0:0);GPC(10:0/0:0);Lysophosphatidylcholine(10:0/0:0);1-Decanoyl-sn-glycero-3-phosphocholine;1-Decanoyl-lysophosphatidylcholine;1-Decanoyl-GPC;LysoPC(10:0);LPC(10:0);GPC(10:0);Lysophosphatidylcholine(10:0)PW_C108327391Capric acidHMDB0000511Capric acid is a member of the series of fatty acids found in oils and animal fats. The names of caproic, caprylic, and capric acids are all derived from the word caper (Latin for goat). These fatty acids are light yellowish transparent oily liquids with uncomfortable smells. They are used in organic synthesis, perfume manufacturing, medicine, lubricating grease, rubber, and dye (Chemicalland21).334-48-5C015712969308133-OXODODECANOATE2863DB03600CCCCCCCCCC(O)=OC10H20O2InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)GHVNFZFCNZKVNT-UHFFFAOYSA-Ndecanoic acid172.2646172.146329884-3.261capric acid0-1FDB0120271-nonanecarboxylate;1-nonanecarboxylic acid;Caprate;Capric acid;Caprinate;Caprinic acid;Caprynate;Caprynic acid;Decoate;Decoic acid;Decylate;Decylic acid;Emery 659;Lunac 10-95;Lunac 10-98;N-caprate;N-capric acid;N-decanoate;N-decanoic acid;N-decoate;N-decoic acid;N-decylate;N-decylic acid;Prifac 2906;Prifac 296;10:0;C10:0;Ch3-[ch2]8-cooh;Decanoate;Dekansaeure;Kaprinsaeure;FA(10:0)PW_C00039110:04299269451607785013212247212412503911812662529912820038810942Glycerol-3-phosphate dehydrogenaseQ00055
Catalyzes the production and accumulation of glycerol during hyperosmotic stress conditions. Glycerol acts as a osmoregulator that prevents loss of water and turgor of the cells.
GPD1291.1.1.8780521013817816313818919810943Glycerol-3-phosphate dehydrogenase GPD2P41911
Catalyzes the production of glycerol under anaerobic growth conditions. Glycerol production serves as a redox sink by consuming the excess cytosolic NADH during anaerobic metabolism.
GPD2,GPD3291.1.1.8780421013817916313819019810658Glycerol-3-phosphate O-acyltransferase 2P36148
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
GTP2292.3.1.15; 2.3.1.4276801607687213780221091261701065418813818019610659Glycerol-3-phosphate O-acyltransferase 1P32784
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase.
SCT1292.3.1.15; 2.3.1.4276791607686213780321091271701065518813818119610661Acyl-CoA:lyso-phospholipid acyltransferaseQ08548
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phospholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol.
ALE1292.3.1.23; 2.3.1.5176831607688213779821091311888040517013818219610662Lipase 4P36165
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL4293.1.1.376851607692213779921091321888040617013818319610663Probable 1-acyl-sn-glycerol-3-phosphate acyltransferaseP33333
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein.
SLC1292.3.1.5176821607689213780021091331888040717013818419610664Lipase 5Q12043
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation.
TGL5293.1.1.376841607691213779721091341888040817013818519610665Lysophosphatidic acid:oleoyl-CoA acyltransferase 1Q06508
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
LOA1292.3.1.5176811607690213779621091351888040917013818619610720Maintenance of mitochondrial morphology protein 1P41800Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. The MDM12-MMM1 subcomplex functions in the major beta-barrel assembly pathway that is responsible for biogenesis of all outer membrane beta-barrel proteins, and acts in a late step after the SAM complex. The MDM10-MDM12-MMM1 subcomplex further acts in the TOM40-specific pathway after the action of the MDM12-MMM1 complex. Essential for establishing and maintaining the structure of mitochondria and maintenance of mtDNA nucleoids.MMM129899724410721Mitochondrial distribution and morphology protein 12Q92328Display
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Functioni
Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM12 is required for the interaction of the ER-resident membrane protein MMM1 and the outer mitochondrial membrane-resident beta-barrel protein MDM10. The MDM12-MMM1 subcomplex functions in the major beta-barrel assembly pathway that is responsible for biogenesis of all mitochondrial outer membrane beta-barrel proteins, and acts in a late step after the SAM complex. The MDM10-MDM12-MMM1 subcomplex further acts in the TOM40-specific pathway after the action of the MDM12-MMM1 complex. Essential for establishing and maintaining the structure of mitochondria and maintenance of mtDNA nucleoids.MDM122910722Mitochondrial distribution and morphology protein 10P18409Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM10 is involved in the late assembly steps of the general translocase of the mitochondrial outer membrane (TOM complex). Functions in the TOM40-specific route of the assembly of outer membrane beta-barrel proteins, including the association of TOM40 with the receptor TOM22 and small TOM proteins. Can associate with the SAM(core) complex as well as the MDM12-MMM1 complex, both involved in late steps of the major beta-barrel assembly pathway, that is responsible for biogenesis of all outer membrane beta-barrel proteins. May act as a switch that shuttles between both complexes and channels precursor proteins into the TOM40-specific pathway. Plays a role in mitochondrial morphology and in the inheritance of mitochondria.MDM1029899824810723Mitochondrial distribution and morphology protein 34P53083Component of the ERMES/MDM complex, which serves as a molecular tether to connect the endoplasmic reticulum and mitochondria. Components of this complex are involved in the control of mitochondrial shape and protein biogenesis and may function in phospholipid exchange. MDM34 is required for the interaction of the ER-resident membrane protein MMM1 and the outer mitochondrial membrane-resident beta-barrel protein MDM10.MDM3429899924810724Protein UPS1, mitochondrialQ05776Required for maintenance of normal mitochondrial morphology as well as PCP1-dependent processing of MGM1. With UPS2, controls the level of cardiolipin in mitochondria. Cardiolipin is a unique phospholipid with four fatty acid chains and is present mainly in the mitochondrial inner membrane where it stabilizes the electron transport chain supercomplex between complexes III and IV through direct interaction of their subunits.UPS12910725Mitochondrial distribution and morphology protein 35O60200Involved in mitochondrial distribution and morphology. Mediates the import of UPS1, UPS2 and UPS3, 3 atypical mitochondrial intermembrane space (IMS) proteins lacking the two major IMS-targeting signals, into the intermembrane space.MDM352910726Phosphatidate cytidylyltransferaseP38221
Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade.
CDS1292.7.7.4176941638041817013819716210727Phosphatidate cytidylyltransferase, mitochondrialP53230
Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
TAM41292.7.7.417693163804191708043216210728CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferaseP25578
Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids.
PGS1292.7.8.5769516076971638043316210729Phosphatidylglycerophosphatase GEP4, mitochondrialP38812
Phosphatidylglycerophosphatase involved in the biosynthesis of cardiolipin (CL), a unique dimeric phosphoglycerolipid predominantly present in mitochondrial membranes and which has important functions for cellular energy metabolism, mitochondrial dynamics and the initiation of apoptotic pathways. Required for the stability of respiratory chain supercomplexes and for growth at elevated temperature, in presence of ethidium bromide or in absence of prohibitins.
GEP4293.1.3.277696160769816313819816210730Cardiolipin synthase (CMP-forming)Q07560
Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) by specifically transferring a phosphatidyl group from CDP-diacylglycerol to phosphatidylglycerol (PG). CL is a key phospholipid in mitochondrial membranes and plays important roles in maintaining the functional integrity and dynamics of mitochondria under both optimal and stress conditions.
CRD1292.7.8.41769916313819916211304Lysophosphatidylcholine acyltransferaseQ06510Acyltransferase which mediates the conversion of 1-acyl-sn-glycero-3-phosphocholine (LPC) into phosphatidylcholine (PC). Displays a broad LPC fatty acyl chain substrate specificity utilizing LPC molecules ranging in length from C-10 to C-20. Does not utilize other lysolipids than LPC as acceptor. Also shows acyl-CoA-independent acyltransferase activity. Required for normal phospholipid content of mitochondrial membranes. Involved in the remodeling of the acyl groups of cardiolipin in the mitochondrial inner membrane, which affects the assembly and stability of respiratory chain complex IV and its supercomplex forms.TAZ1292.3.1.23922216313820116223176Cardiolipin-specific deacylase 1, mitochondrialP53264
Mitochondrial cardiolipin-specific phospholipase which deacylates de novo synthesized cardiolipin. Part of the remodeling process of cardiolipin, which involves deacylation-reacylation of premature cardiolipin. Has a strong substrate preference for palmitic acid residues and generates monolysocardiolipin for TAZ1-dependent reacylation with unsaturated fatty acids.
CLD1293.5.1.-1382001624720Glycerol-3-phosphate dehydrogenase18PW_P004720119021094211903109434341Glycerol-3-phosphate O-acyltransferase 18PW_P004341114041065811405106594343Lysophosphatidate acyltransferase18PW_P004343114071066111408106621140910663114101066411411106654392ERMES COMPLEX18PW_P00439211472107201147310721114741072211475107234393Ups1/Mdm35p heterodimer18PW_P004393114761072411477107254394Phosphatidate cytidylyltransferase18PW_P004394114781072611479107274395CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase18PW_P00439511480107284396Phosphatidylglycerophosphatase GEP4, mitochondrial18PW_P00439611481107294397Cardiolipin synthase (CMP-forming)18PW_P00439711482107305054Lysophosphatidylcholine acyltransferase18PW_P005054123461130413896Ccardiolipin-specific phospholipase18PW_P0138962381323176187406PW_R187406Both71004111341Compoundfalse71004211441Compoundfalse710043400341Compoundfalse710044811Compoundfalse7100457211Compoundfalse1770654720187432PW_R187432Right71013727421Compoundfalse710138811Compoundfalse71013910991Compoundfalse710140553621Compoundfalse17707943412.3.1.15187433PW_R187433Right710141553621Compoundfalse71014227421Compoundfalse710143555121Compoundfalse71014410991Compoundfalse17708043432.3.1.238041falsePW_R008041Right33697555121Compoundfalse33698400341Compoundfalse33699571Compoundfalse337001701Compoundfalse33701426841Compoundfalse804043942.7.7.418042falsePW_R008042Right33702426841Compoundfalse33703811Compoundfalse33704438641Compoundfalse33705400341Compoundfalse33706641Compoundfalse804143952.7.8.58043falsePW_R008043Right33707438641Compoundfalse3370814201Compoundfalse3370911041Compoundfalse33710438531Compoundfalse804243963.1.3.27187627PW_R187627Right710918438531Compoundfalse7109191082481Compoundfalse710920459431Compoundfalse710921641Compoundfalse710922400341Compoundfalse17727443972.7.8.41187628PW_R187628Right7109231052271Compoundfalse710924556651Compoundfalse710925459431Compoundfalse7109261083271Compoundfalse17727550542.3.1.23187629PW_R187629Right710927459431Compoundfalse71092814201Compoundfalse7109293911Compoundfalse7109301052271Compoundfalse177276138963.5.1.-10438PW_T01043810812555121Compound213199Right161043922019-12-13T11:09:10-07:002019-12-13T11:09:10-07:0021310439PW_T01043910813555121Compound199162Right161143932019-12-13T11:09:12-07:002019-12-13T11:09:12-07:00162276115811341983false30134510regular1001102761159114419860false40630010regular503027611604003419855false37247510regular787827611614003416255false1420139810regular787827611624003416255false1423209710regular787827611634003416255false676220410regular78782761164812133false70134710regular1001102761165811623false1401190610regular100110276116672119859false65130210regular5030276116727422133false75148210regular1001002761168109921385false109870710regular50302761169109921385false106630210regular50302761170553622133false113135210regular100100276117127422133false124142710regular1001002761172555122133false113375710regular1001002761173555121993false1133111210regular1001002761174555121623false1523127710regular1001002761175571623false1398148710regular100110276117617016245false1436172510regular63432761177426841623false1521179610regular1001102761178438641623false1521232110regular1001002761179641623false1406219610regular1001102761180641623false550216910regular1001102761181142016249false1276220410regular78782761182142016249false552193510regular78782761183110416246false1068224010regular44432761184438531623false975232010regular10010027611851082481623false900217010regular1001102761186459431623false420231910regular1001002761187459431623false899127910regular10010027611881052271623false419165910regular1001002761189556651623false579139910regular10010027611901083271623false819140410regular10010027611913911623false549176410regular100100982781109421982true5763928subunitregular15070982782109431982false4763678subunitregular15070982783106582132false8864148subunitregular15070982784106592132false8863698subunitregular15070982785106612132false11065378subunitregular15070982786106622132false11965528subunitregular15070982787106632132false11065728subunitregular15070982788106642132false11965928subunitregular15070982789106652132false11066078subunitregular150709827901072076false10539128subunitregular150709827911072176false11589128subunitregular150709827921072276false11589628subunitregular150709827931072376false10539628subunitregular150709827941072476false115812928subunitregular150709827951072576false105812928subunitregular15070982796107261622true136515018subunitregular15070982797107271622false150016018subunitregular15070982798107281622false149620238subunitregular15070982799107291622false113023358subunitregular15070982800107301622false75023348subunitregular15070982801113041622false67712918subunitregular15070982802231761622false39518668subunitregular15070830970472033521989785119827819785129827828309714341335221397851398278397851498278483097243433352213978515982785978516982786978517982787978518982788978519982789830973439233529785209827909785219827919785229827929785239827938309744393335297852498279497852598279583097543943352162978526982796978527982797830976439533521629785289827988309774396335216297852998279983097843973352162978530982800830979505433521629785319828018309801389633521629785329828023783888M401 400 C431 400 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3783889M431 330 C429 377 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3783890M411 475 C410 437 446 402 476 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3783891M701 402 C671 402 656 402 626 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3783892M676 332 C675 381 651 402 626 402 5false18trueM 308.94685504416486 297.261556296296 L 294 296 L 300.38088772118584 309.5751343230783false3783893M801 482 C811 418 856 404 886 404 5false183783894M801 402 C831 402 856 404 886 404 5false183783895M1091 332 C1092 370 1066 404 1036 404 5false18trueM 148.94685504416483 260.261556296296 L 134 259 L 140.38088772118584 272.5751343230783false3783896M1131 402 C1101 402 1066 404 1036 404 5false18trueM 148.94685504416483 260.261556296296 L 134 259 L 140.38088772118584 272.5751343230783false3783897M1181 452 C1181 482 1181 507 1181 537 5false183783898M1241 477 C1217 474 1183 488 1181 537 5false183783899M1183 757 C1183 731 1181 707 1181 677 5false18trueM 531.9468550441649 202.26155629629605 L 517 201 L 523.3808877211858 214.57513432307834false3783900M1148 722 C1184 717 1181 707 1181 677 5false18trueM 531.9468550441649 202.26155629629605 L 517 201 L 523.3808877211858 214.57513432307834false3783901M1183 857 C1183 887 1183 883 1183 913 83false18trueM 1120.5 949.0096189432334 L 1128 962 L 1135.5 949.0096189432334false3783902M1183 1112 C1183 1082 1183 1062 1183 1032 83false18trueM 499.94685504416486 543.261556296296 L 485 542 L 491.38088772118584 555.5751343230784false3783903M1183 1212 C1183 1234 1184 1260 1184 1288 83false18trueM 1045.0096189432334 1334.5 L 1058 1327 L 1045.0096189432334 1319.5false3783904M1523 1327 C1493 1327 1338 1327 1308 1327 83false18trueM 510.94685504416486 828.261556296296 L 496 827 L 502.38088772118584 840.5751343230784false3783905M1573 1377 C1573 1407 1575 1571 1575 1601 5false183783906M1498 1542 C1536 1541 1575 1574 1575 1601 5false183783907M1498 1437 C1562 1437 1575 1571 1575 1601 5false183783908M1499 1746.5 C1544 1749.5 1575 1701 1575 1671 5false18trueM 896.9468550441649 1189.261556296296 L 882 1188 L 888.3808877211858 1201.5751343230784false3783909M1571 1796 C1571 1766 1575 1701 1575 1671 5false18trueM 896.9468550441649 1189.261556296296 L 882 1188 L 888.3808877211858 1201.5751343230784false3783910M1571 1906 C1571 1936 1571 1993 1571 2023 5false183783911M1501 1961 C1542 1960 1571 1993 1571 2023 5false183783912M1571 2321 C1571 2291 1571 2123 1571 2093 5false18trueM 812.9468550441649 1736.261556296296 L 798 1735 L 804.3808877211858 1748.5751343230784false3783913M1501 2136 C1555 2130 1571 2123 1571 2093 5false18trueM 812.9468550441649 1736.261556296296 L 798 1735 L 804.3808877211858 1748.5751343230784false3783914M1506 2251 C1558 2247 1571 2123 1571 2093 5false18trueM 812.9468550441649 1736.261556296296 L 798 1735 L 804.3808877211858 1748.5751343230784false3783915M1521 2371 C1491 2371 1310 2370 1280 2370 5false183783916M1315 2282 C1311 2315 1310 2370 1280 2370 5false183783917M1090 2283 C1091 2324 1100 2370 1130 2370 5false18trueM 802.9468550441649 1878.261556296296 L 788 1877 L 794.3808877211858 1890.5751343230784false3783918M1075 2370 C1105 2370 1100 2370 1130 2370 5false18trueM 802.9468550441649 1878.261556296296 L 788 1877 L 794.3808877211858 1890.5751343230784false3783919M975 2370 C945 2370 930 2369 900 2369 5false183783920M950 2280 C949 2330 930 2369 900 2369 5false183783921M530 2369 C560 2369 720 2369 750 2369 5false18trueM 276.94685504416486 1934.261556296296 L 262 1933 L 268.38088772118584 1946.5751343230784false3783922M600 2279 C610 2370 720 2369 750 2369 5false18trueM 276.94685504416486 1934.261556296296 L 262 1933 L 268.38088772118584 1946.5751343230784false3783923M715 2282 C714 2335 720 2369 750 2369 5false18trueM 276.94685504416486 1934.261556296296 L 262 1933 L 268.38088772118584 1946.5751343230784false3783924M469 1659 C469 1621 468 1349 468 1327 C495 1327 642 1327 677 1326 5false183783925M629 1399 C628 1357 647 1326 677 1326 5false183783926M899 1329 C869 1329 857 1326 827 1326 5false18trueM 64.94685504416483 1194.261556296296 L 50 1193 L 56.38088772118584 1206.5751343230784false3783927M874 1399 C877 1358 857 1326 827 1326 5false18trueM 64.94685504416483 1194.261556296296 L 50 1193 L 56.38088772118584 1206.5751343230784false3783928M470 2319 C470 2289 470 1966 470 1936 5false183783929M552 1974 C515 1971 470 1966 470 1936 5false183783930M549 1814 C507 1812 470 1836 470 1866 5false18trueM 50.946855044164835 1420.261556296296 L 36 1419 L 42.38088772118584 1432.5751343230784false3783931M469 1759 C469 1789 470 1836 470 1866 5false18trueM 50.946855044164835 1420.261556296296 L 36 1419 L 42.38088772118584 1432.5751343230784false8241663352187406332807827611583783888Left332807927611593783889Left332808027611603783890Left332808127611643783891Right332808227611663783892Right7792881770658309708241673352187432332808327611673783893Left332808427611643783894Left332808527611693783895Right332808627611703783896Right7792891770668309718241683352187433332808727611703783897Left332808827611713783898Left332808927611723783899Right332809027611683783900Right77929017706783097282416933528041332809127611743783905Left332809227611753783906Left332809327611613783907Left332809427611763783908Right332809527611773783909Right77929117706883097582417033528042332809627611773783910Left332809727611653783911Left332809827611783783912Right332809927611623783913Right332810027611793783914Right77929217707083097682417133528043332810127611783783915Left332810227611813783916Left332810327611833783917Right332810427611843783918Right77929364228309778241723352187627332810527611843783919Left332810627611853783920Left332810727611863783921Right332810827611803783922Right332810927611633783923Right7792941770718309788241733352187628332811027611883783924Left332811127611893783925Left332811227611873783926Right332811327611903783927Right7792951770758309798241743352187629332811427611863783928Left332811527611823783929Left332811627611913783930Right332811727611883783931Right7792961770788309807901110438335215909727611723783901Left15909827611733783902Right2544083097316087901210439335215909927611733783903Left15910027611743783904Right25441830974160944095014256351.11.1-1052328036044095113815811.11.10214327267440952172811360.80.8-17041490240419592M705 523 C705 473 755 423 805 423 C905 423 1034 423 1134 423 C1184 423 1234 473 1234 523 C1234 629 1234 768 1234 874 C1234 924 1184 974 1134 974 C1034 974 905 974 805 974 C755 974 705 924 705 874 C705 768 705 629 705 523 91true6529.0551.0419593M326 1277 C326 1227 376 1177 426 1177 C790 1177 1262 1177 1626 1177 C1676 1177 1726 1227 1726 1277 C1726 1625 1726 2077 1726 2425 C1726 2475 1676 2525 1626 2525 C1262 2525 790 2525 426 2525 C376 2525 326 2475 326 2425 C326 2077 326 1625 326 1277 84true61400.01348.0419594M475 1427 C475 1377 525 1327 575 1327 C848 1327 1203 1327 1476 1327 C1526 1327 1576 1377 1576 1427 C1576 1684 1576 2018 1576 2275 C1576 2325 1526 2375 1476 2375 C1203 2375 848 2375 575 2375 C525 2375 475 2325 475 2275 C475 2018 475 1684 475 1427 84true61101.01048.0419595M226 326 C226 276 276 226 326 226 C750 226 1301 226 1725 226 C1775 226 1825 276 1825 326 C1825 993 1825 1860 1825 2527 C1825 2577 1775 2627 1725 2627 C1301 2627 750 2627 326 2627 C276 2627 226 2577 226 2527 C226 1860 226 993 226 326 1true61599.02401.0419596M126 226 C126 176 176 126 226 126 C711 126 1341 126 1826 126 C1876 126 1926 176 1926 226 C1926 953 1926 1897 1926 2624 C1926 2674 1876 2724 1826 2724 C1341 2724 711 2724 226 2724 C176 2724 126 2674 126 2624 C126 1897 126 953 126 226 1true61800.02598.084162515Endoplasmic Reticulum Membrane690871202.02.01601584162615Mitochondria7851582202.82.81601584162715Cytoplasm291602201.91.91601526032714434566793981260100040#FFEEDE458160226032815989653001151175225514#FFEBEB414521400