7505PathwayTriacylglycerol Metabolism TG(10:0/10:0/26:1(5Z))A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. The biosynthesis of triacylglycerol is localized to the endoplasmic reticulum membrane and starts with glycerol 3-phosphate reacting with acyl-CoA through a glycerol-3-phosphate O-acyltransferase resulting in the release of lysophosphatidic acid (LPA). This, in turn, reacts with an acyl-CoA through a lipase complex resulting in the release of CoA and phosphatidic acid. Phosphatidic acid reacts with water through a phosphatidic acid phosphohydrolase 1 resulting in the release of a phosphate and a diacylglycerol. This reaction can be reversed through a CTP-dependent diacylglycerol kinase. The diacylglycerol reacts in the endoplasmic reticulum with an acyl-CoA through a diacylglycerol O-acyltransferase resulting in the release of coenzyme A and a triacylglycerol. Triacylglycerol metabolism begins with a reaction with water through lipase resulting in the release of a fatty acid, hydrogen ion, and a diacylglycerol. Diacylglycerol then reacts with a lipase 3 resulting in the release of a fatty acid and a monoacylglycerol. Monoacylglycerol reacts with monoglyceride lipase resulting in the release of a fatty acid in glycerol.MetabolicPW007711CenterPathwayVisualizationContext799614503130#000099PathwayVisualization74677505Triacylglycerol Metabolism TG(10:0/10:0/26:1(5Z))A triglyceride (TG, triacylglycerol, TAG, or triacylglyceride) is an ester derived from glycerol and three fatty acids. The biosynthesis of triacylglycerol is localized to the endoplasmic reticulum membrane and starts with glycerol 3-phosphate reacting with acyl-CoA through a glycerol-3-phosphate O-acyltransferase resulting in the release of lysophosphatidic acid (LPA). This, in turn, reacts with an acyl-CoA through a lipase complex resulting in the release of CoA and phosphatidic acid. Phosphatidic acid reacts with water through a phosphatidic acid phosphohydrolase 1 resulting in the release of a phosphate and a diacylglycerol. This reaction can be reversed through a CTP-dependent diacylglycerol kinase. The diacylglycerol reacts in the endoplasmic reticulum with an acyl-CoA through a diacylglycerol O-acyltransferase resulting in the release of coenzyme A and a triacylglycerol. Triacylglycerol metabolism begins with a reaction with water through lipase resulting in the release of a fatty acid, hydrogen ion, and a diacylglycerol. Diacylglycerol then reacts with a lipase 3 resulting in the release of a fatty acid and a monoacylglycerol. Monoacylglycerol reacts with monoglyceride lipase resulting in the release of a fatty acid in glycerol.Metabolic1833411010515935Athenstaedt K, Zweytick D, Jandrositz A, Kohlwein SD, Daum G: Identification and characterization of major lipid particle proteins of the yeast Saccharomyces cerevisiae. J Bacteriol. 1999 Oct;181(20):6441-8.7505Pathway33411116916618Czabany T, Athenstaedt K, Daum G: Synthesis, storage and degradation of neutral lipids in yeast. Biochim Biophys Acta. 2007 Mar;1771(3):299-309. doi: 10.1016/j.bbalip.2006.07.001. Epub 2006 Jul 13.7505Pathway33411216267052Kurat CF, Natter K, Petschnigg J, Wolinski H, Scheuringer K, Scholz H, Zimmermann R, Leber R, Zechner R, Kohlwein SD: Obese yeast: triglyceride lipolysis is functionally conserved from mammals to yeast. J Biol Chem. 2006 Jan 6;281(1):491-500. doi: 10.1074/jbc.M508414200. Epub 2005 Nov 2.7505Pathway33411322345606Henry SA, Kohlwein SD, Carman GM: Metabolism and regulation of glycerolipids in the yeast Saccharomyces cerevisiae. Genetics. 2012 Feb;190(2):317-49. doi: 10.1534/genetics.111.130286.7505Pathway1CellCL:00000005HepatocyteCL:00001824Cardiomyocyte CL:00007463NeuronCL:00005407Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog60Nitzschia sp.0001EukaryoteNitzschia42Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel29Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast2MitochondrionGO:00057393Mitochondrial MatrixGO:000575914Mitochondrial Outer MembraneGO:00057417Endoplasmic Reticulum MembraneGO:00057895CytoplasmGO:00057371CytosolGO:000582924Mitochondrial Intermembrane SpaceGO:000575831Periplasmic SpaceGO:000562012Mitochondrial Inner MembraneGO:000574313Endoplasmic ReticulumGO:000578327Peroxisome MembraneGO:00057784PeroxisomeGO:00057778Smooth Endoplasmic Reticulum GO:000579010Cell MembraneGO:000588632Inner MembraneGO:00702586LysosomeGO:000576411Extracellular SpaceGO:000561516Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520215NucleusGO:000563435ChloroplastGO:000950736MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:004259719sarcoplasmic reticulumGO:00165291LiverBTO:00007597294Adrenal MedullaBTO:000004971825IntestineBTO:000064828StomachBTO:0001307155267Nervous SystemBTO:00014848Blood VesselBTO:0001102741111HeartBTO:000056273103211PW_BS0000034311PW_BS000004103331PW_BS0001031613181PW_BS0001611632181PW_BS000163221411PW_BS00002249711PW_BS0000491333121PW_BS0001331122121PW_BS000112406351PW_BS000115407251PW_BS0001151203171PW_BS0001201192171PW_BS0001194793101PW_BS000115501361PW_BS0001158511PW_BS0000082111PW_BS000002422411PW_BS0000425811411PW_BS000058107313PW_BS00010710813PW_BS00010816212181PW_BS00016217018PW_BS000170188118PW_BS000024151141PW_BS0001512231241PW_BS0000242491341PW_BS000024171211PW_BS0000173183123PW_BS000024315123PW_BS0000241115121PW_BS000111350114121PW_BS00002834524121PW_BS0000281321121PW_BS00013213412121PW_BS000134253541PW_BS000024124151PW_BS0001243841251PW_BS000100388161PW_BS0001123911261PW_BS0001121181171PW_BS000118122551PW_BS0001224182451PW_BS00011512112171PW_BS00012143311451PW_BS0001151355171PW_BS00013545424171PW_BS000115468114171PW_BS0001152975101PW_BS00002448924101PW_BS0001152991101PW_BS000024205561PW_BS0000245062461PW_BS000115592711PW_BS0000595411PW_BS00000529111PW_BS000029311511PW_BS000031111811PW_BS000011181311PW_BS000018101711PW_BS00001014101PW_BS000014541315PW_BS0000546131PW_BS0000061021231PW_BS0001021041431PW_BS000104101531PW_BS0001011553241PW_BS00015511PW_BS0000011783211PW_BS0001781601181PW_BS00016019914181PW_BS0000241985181PW_BS00002421013181PW_BS000024222341PW_BS000024226441PW_BS000024224241PW_BS0000241951318PW_BS00002429341PW_BS00002432914121PW_BS0000283344121PW_BS0000283361121PW_BS00002812915121PW_BS0001291151012PW_BS00011533217121PW_BS00002833527121PW_BS00002813013121PW_BS0001303331212PW_BS0000283317121PW_BS0000283683601PW_BS0000283744171PW_BS0000533761017PW_BS0000533821451PW_BS000100383751PW_BS0001002881441PW_BS0000243891461PW_BS000112390761PW_BS00011239914171PW_BS0001133987171PW_BS000113405105PW_BS000115117131PW_BS0001171231751PW_BS0001231251351PW_BS000125429151PW_BS000115408451PW_BS0001154141551PW_BS0001154222751PW_BS00011544717171PW_BS00011513613171PW_BS0001364641171PW_BS00011545015171PW_BS00011537527171PW_BS0000534781010PW_BS00011548012101PW_BS00011548414101PW_BS0001154812101PW_BS00011549127101PW_BS0001154824101PW_BS00011530013101PW_BS000024209106PW_BS000024206261PW_BS0000245082761PW_BS000115502461PW_BS0001153951361PW_BS0001131893218PW_BS0000241971418PW_BS0000249611PW_BS00000913121PW_BS00001315111PW_BS0000152811611PW_BS000028204111PW_BS000020331811PW_BS000033432511PW_BS0000432441011PW_BS00002460251PW_BS00006046114PW_BS0000467028511PW_BS00007072513PW_BS000072612517PW_BS0000613612011PW_BS0000363772113PW_BS00003793252011PW_BS00009327151PW_BS000027711PW_BS000007971521PW_BS000097100521PW_BS000100943PW_BS000094105113PW_BS0001051136121PW_BS000113110231PW_BS000110126651PW_BS00012612711651PW_BS0001271141112PW_BS000114140103PW_BS00014014315191PW_BS0001431465191PW_BS000146951721PW_BS0000951471241PW_BS0001471572241PW_BS00015715924PW_BS00015916611PW_BS0001661802211PW_BS00018015284PW_BS000152207661PW_BS0000242111018PW_BS0000242137181PW_BS00002421425181PW_BS0000242156181PW_BS0000242164181PW_BS00002421217181PW_BS0000241901118PW_BS0000242253541PW_BS000024261115PW_BS0000262771218PW_BS0000241644PW_BS0001642811251PW_BS0000242851041PW_BS0000242863641PW_BS0000242875341PW_BS0000242273441PW_BS00002465111PW_BS0000652905491PW_BS0000242916491PW_BS0000242924491PW_BS00002429817101PW_BS0000243016101PW_BS000024302116101PW_BS0000242941141PW_BS0000243081011PW_BS0000243221231PW_BS000024337116121PW_BS00002834141121PW_BS00002834318121PW_BS00002834713125PW_BS0000283522512PW_BS00002835325127PW_BS00002835625121PW_BS000028360410121PW_BS0000283702601PW_BS000028228361PW_BS000024232403PW_BS000024412125PW_BS000115409115PW_BS0001154151851PW_BS0001154251355PW_BS0001154192551PW_BS00011543441051PW_BS000115436255PW_BS0001154436171PW_BS0001154461217PW_BS0001151371117PW_BS000137448116171PW_BS00011545118171PW_BS00011546013175PW_BS00011545525171PW_BS000115469410171PW_BS0001154712517PW_BS00011547225177PW_BS0001154831110PW_BS00011548718101PW_BS00011549025101PW_BS0001154957101PW_BS000115208116PW_BS0000245041861PW_BS0001155072561PW_BS00011551541061PW_BS0001155131761PW_BS000115471914PW_BS000047231511PW_BS000023241529PW_BS00002425715291PW_BS00002430412PW_BS000024109323PW_BS00010912815121PW_BS0001284101551PW_BS00011544415171PW_BS00011548515101PW_BS0001151873118PW_BS000024219314PW_BS00002422014PW_BS0000243125231PW_BS0000243201123PW_BS00002432711125PW_BS000028310312PW_BS0000244241155PW_BS00011545911175PW_BS000115196718PW_BS0000242742Decanoyl-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_C002742Decanoy8633916452891036987161711716325496222549949772431337788111212025540612064940712292912012326611912560647912713350181Glycerol 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_C000081Glyc1P10438147521488422115586295107629610884121629122170106531881254615112550223153192493481417424663184246731578030111780523507837234578378132799521348180825393826124947893841105533881106363911158401181207561221212974181213451211214154331233531351238674541239744681257882971259784891259912991272432051274315061099Coenzyme 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 10149189101511971065718825500491420WaterHMDB0002111Water 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_C001420H2O558949109513941513162144811352615624286521069120770338231883821094311377491465541590432018242532222678602727462778172805293143703164723634614598364727374941935030275156751959752141005227945236103529710553191115343113535511254021105470123548312554921265507127553413055371145541129559113556081185622108569165759140577810158411435853146587710758909559101475940151603215560591576087161612316361331596215162181666477178650718066001526713117684018868881607162205718120771932067211211722821372382147243215729519873502167388210740121274672227492224750019075881708201225823722684141629265261185027711922164120112811221328512250286122642871232724912520227126326512693290127052911271529213007298130193001302530113037302132612231332729415340308423273154269531843691322769142937701925377102132771311337721513477378331773973327747133377516115775363347762833677722337777593417781634377982347780713297823535278242353782703567911336080014368800393708059122880656119938303839479438411055739011063939111584439811987923211991512211996340612000840712004640812011312412036541212043040512043840912060641512079441412115842512124042912135112112138141912160743412211838212238443612275312012279737412280444312301244612306437612307213712313144712314213612316244812323145112338445012373046012381046412394045512416546912467039912493847112494547212530529712535347912538648112542448212548029912568248312570747812574548712605449012623849512627348412676448012689650112696350212701738812717720812719920912722750412750650712757651512783638912808239512817651343337DG(10:0/10:0/0:0)DG(10:0/10:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(10:0/10:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.C00165DIACYLGLYCEROL[H][C@@](CO)(COC(=O)CCCCCCCCC)OC(=O)CCCCCCCCCC23H44O5InChI=1S/C23H44O5/c1-3-5-7-9-11-13-15-17-22(25)27-20-21(19-24)28-23(26)18-16-14-12-10-8-6-4-2/h21,24H,3-20H2,1-2H3/t21-/m1/s1GNSDEDOVXZDMKM-OAQYLSRUSA-N(2R)-1-(decanoyloxy)-3-hydroxypropan-2-yl decanoate400.6400.318874517-5.811(R)-1,2-didecanoylglycerol00(2-decanoyloxy-3-hydroxypropyl) decanoate;1,2-dicaprin;1,2-didecanoyl-rac-glycerol;3-hydroxypropane-1,2-diyl didecanoate;Dag(10:0/10:0);Dag(20:0);Dg(10:0/10:0);Dg(20:0);Diacylglycerol;Diacylglycerol(10:0/10:0);Diacylglycerol(20:0);DiglyceridePW_C043337DG20:09291195106581601066017025501491104PhosphateHMDB0001429Phosphate is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry, biogeochemistry and ecology. Phosphate (Pi) is an essential component of life. In biological systems, phosphorus is found as a free phosphate ion in solution and is called inorganic phosphate, to distinguish it from phosphates bound in various phosphate esters. Inorganic phosphate is generally denoted Pi and at physiological (neutral) pH primarily consists of a mixture of HPO<sup>2-</sup><sub>4</sub> and H<sub>2</sub>PO<sup>-</sup><sub>4</sub> ions. phosphates are most commonly found in the form of adenosine phosphates, (AMP, ADP and ATP) and in DNA and RNA and can be released by the hydrolysis of ATP or ADP. Similar reactions exist for the other nucleoside diphosphates and triphosphates. Phosphoanhydride bonds in ADP and ATP, or other nucleoside diphosphates and triphosphates, contain high amounts of energy which give them their vital role in all living organisms. Phosphate must be actively transported into cells against its electrochemical gradient. In vertebrates, two unrelated families of Na+-dependent Pi transporters carry out this task. Remarkably, the two families transport different Pi species: whereas type II Na+/Pi cotransporters (SCL34) prefer divalent HPO4(2), type III Na+/Pi cotransporters (SLC20) transport monovalent H2PO4. The SCL34 family comprises both electrogenic and electroneutral members that are expressed in various epithelia and other polarized cells. Through regulated activity in apical membranes of the gut and kidney, they maintain body Pi homeostasis, and in salivary and mammary glands, liver, and testes they play a role in modulating the Pi content of luminal fluids. Phosphate levels in the blood play an important role in hormone signaling and in bone homeostasis. In classical endocrine regulation, low serum phosphate induces the renal production of the seco-steroid hormone 1,25-dihydroxyvitamin D3 (1,25(OH)2D3).This active metabolite of vitamin D acts to restore circulating mineral (i.e. phosphate and calcium) levels by increasing absorption in the intestine, reabsorption in the kidney, and mobilization of calcium and phosphate from bone. Thus, chronic renal failure is associated with hyperparathyroidism, which in turn contributes to osteomalacia (softening of the bones). Another complication of chronic renal failure is hyperphosphatemia (low levels of phosphate in the blood). Hyperphosphatemia (excess levels of phosphate in the blood) is a prevalent condition in kidney dialysis patients and is associated with increased risk of mortality. Hypophosphatemia (hungry bone syndrome) has been associated to postoperative electrolyte aberrations and after parathyroidectomy. (PMID: 17581921, 11169009, 11039261, 9159312, 17625581)Fibroblast growth factor 23 (FGF-23) has recently been recognized as a key mediator of phosphate homeostasis, its most notable effect being promotion of phosphate excretion. FGF-23 was discovered to be involved in diseases such as autosomal dominant hypophosphatemic rickets, X-linked hypophosphatemia, and tumor-induced osteomalacia in which phosphate wasting was coupled to inappropriately low levels of 1,25(OH)2D3. FGF-23 is regulated by dietary phosphate in humans. In particular it was found that phosphate restriction decreased FGF-23, and phosphate loading increased FGF-23.14265-44-2C00009106118367CPD-85871032[O-]P([O-])([O-])=OO4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)/p-3NBIIXXVUZAFLBC-UHFFFAOYSA-Kphosphoric acid94.971494.953423phosphoric acid0-2DBMET00532FDB022617Nfb orthophosphate;O-phosphoric acid;Ortho-phosphate;Orthophosphate (po43-);Orthophosphate(3-);Phosphate;Phosphate (po43-);Phosphate anion(3-);Phosphate ion (po43-);Phosphate ion(3-);Phosphate trianion;Phosphate(3-);Phosphoric acid ion(3-);Pi;[po4](3-);Orthophosphate;Phosphate ion;Po4(3-);Phosphoric acid;Orthophosphoric acid;Phosphoric acid ionPW_C001104Pi244848814581818831298031763141767492500102729472737463129293166723636613851234249224475315031275158752079752161005317111535111253811035447120554312955731335605135562510856936584814358551465911147594115160401556100161629410764871786691101671411768421886889160716120571892067212211730619873892107402212743616374752228196225825822710118241101342571174813211761115117732131190417011927164120142811272829013263223348191742255304423503154243531843692322770182537719429377217134779403367796613078048332780573297824535378669331800223688927930893831383947963841105583901106403911132359411584539811620610911998240612006912212069940712105712412121612512126842912135212112140912312142338212185240512330411912362111812378613612383846412396844712398139912440537612494847212536247912544629712577448112595429912622147812659430012660429812672348412690450112741338812778320912816639512817751312831538957Cytidine triphosphateHMDB0000082Cytidine 5'-(tetrahydrogen triphosphate) or CTP is a cytosine nucleotide containing three phosphate groups esterified to a ribose moiety at the 5' position. CTP is integral to the synthesis or mRNA, rRNA and tRNA through RNA polymerases. Cytidine triphosphate (CTP) is also critical to the synthesis of phosphatidylcholine via the enzyme CTP: phosphocholine cytidyltransferase. This reaction is the rate-limiting step in the synthesis of phosphatidylcholine.65-47-4C00063617617677CTP5941DB02431NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H16N3O14P3InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1PCDQPRRSZKQHHS-XVFCMESISA-N({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid483.1563482.984511771-1.647CTP0-3FDB0128335'-(tetrahydrogen triphosphate) cytidine;5'-ctp;Ctp;Cytidine 3'-triphosphate;Cytidine 5'-(tetrahydrogen triphosphate);Cytidine 5'-triphosphate;Cytidine 5'-triphosphoric acid;Cytidine 5-prime-triphosphate;Cytidine triphosphate;Cytidine mono;Cytidine mono(tetrahydrogen triphosphate) (ester);Cytidine-5'-triphosphate;Deoxycytosine triphosphate;H4ctpPW_C000057CTP4272311508271825766101580010870771887593160913719591422131219416412510288152851511531724915342221537418347591742650315773151287844811178733132799491347995713079964329804161709478438494812125948173829867722311063339111326839511327338911552513611553039912032841012085412212134012112221212412298344412343413512476411812565448512584029712637429912729220512793538840034Hydrogen 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+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951189CDPHMDB0001546CDP, also known as 5'-cdp, belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. CDP is soluble (in water) and a moderately acidic compound (based on its pKa). CDP has been primarily detected in blood. Within the cell, CDP is primarily located in the mitochondria, nucleus and cytoplasm. In humans, CDP is involved in the pyrimidine metabolism pathway. CDP is also involved in several metabolic disorders, some of which include dihydropyrimidinase deficiency, UMP synthase deficiency (orotic aciduria), the mngie (mitochondrial neurogastrointestinal encephalopathy) pathway, and Beta ureidopropionase deficiency. Cytidine 5\'-(trihydrogen diphosphate). A cytosine nucleotide containing two phosphate groups esterified to the sugar moiety. Synonyms: CRPP; cytidine pyrophosphate.63-38-7C00112613217239CDP5902NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC9H15N3O11P2InChI=1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1ZWIADYZPOWUWEW-XVFCMESISA-N[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid403.1764403.018181361-1.606CDP0-2FDB022683Cdp;Cytidine-5'-diphosphate;Cytidine-diphosphate;5'-cdp;Cytidine 5'-diphosphate;Cytidine 5'-diphosphoric acid;Cytidine 5'-pyrophosphate;Cytidine diphosphate;Cytidine, 5'-(trihydrogen pyrophosphate);Cytidine 5'-pyrophosphoric acid;Cytidine diphosphoric acid;Cytidine, 5'-(trihydrogen pyrophosphoric acid);Cytidine-5'-diphosphoric acidPW_C001189CDP273329140195914321378735132122215124124767118126377299127939388108374(5Z)-Hexacosenoyl-CoA(5Z)-Hexacosenoyl-CoA is a fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of (5Z)-hexacosenoic acid.CCCCCCCCCCCCCCCCCCCC\C=C/CCCC(=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=C2NC47H84N7O17P3SInChI=1S/C47H84N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-38(56)75-31-30-49-37(55)28-29-50-45(59)42(58)47(2,3)33-68-74(65,66)71-73(63,64)67-32-36-41(70-72(60,61)62)40(57)46(69-36)54-35-53-39-43(48)51-34-52-44(39)54/h23-24,34-36,40-42,46,57-58H,4-22,25-33H2,1-3H3,(H,49,55)(H,50,59)(H,63,64)(H,65,66)(H2,48,51,52)(H2,60,61,62)/b24-23-/t36-,40-,41-,42+,46-/m1/s1JMJSQBUPNGHWIE-BLSRMLOTSA-N1144.21143.485726441-4.52(5Z)-Hexacosenoyl-CoA;CoA(26:1(5Z))PW_C108374CoA26:157282TG(10:0/10:0/26:1(5Z))TG(10:0/10:0/26:1(5Z)) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(10:0/10:0/26:1(5Z)) is made up of one decanoyl(R1), one decanoyl(R2), and one 5Z-hexacosenoyl(R3).[H][C@](COC(=O)CCCCCCCCC)(COC(=O)CCC\C=C/CCCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCC49H92O6InChI=1S/C49H92O6/c1-4-7-10-13-16-17-18-19-20-21-22-23-24-25-26-27-28-29-30-31-34-36-39-42-48(51)54-45-46(55-49(52)43-40-37-33-15-12-9-6-3)44-53-47(50)41-38-35-32-14-11-8-5-2/h31,34,46H,4-30,32-33,35-45H2,1-3H3/b34-31-/t46-/m0/s1OZLNTNUFYRVDIP-KRNPDENESA-N(2S)-2,3-bis(decanoyloxy)propyl (5Z)-hexacos-5-enoate777.269776.689390682-7.830(2S)-2,3-bis(decanoyloxy)propyl (5Z)-hexacos-5-enoate00PW_C057282TG10959163108373(5Z)-Hexacosenoic acid(5Z)-Hexacosenoic acid is a monounsaturated fatty acid that has a 26-carbon chain with a double bond at carbon 5.CCCCCCCCCCCCCCCCCCCC\C=C/CCCC(O)=OC26H50O2InChI=1S/C26H50O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26(27)28/h21-22H,2-20,23-25H2,1H3,(H,27,28)/b22-21-XGHRLMLHBKEUAP-DQRAZIAOSA-N(5Z)-hexacos-5-enoic acid394.684394.38108085-7.361(5Z)-hexacos-5-enoic acid0-1(5Z)-Hexacosenoic acid;FA(26:1(5Z))PW_C108373C26:17160MG(16:0/0:0/0:0)HMDB0011564MG(16:0/0:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups: 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. MG(16:0/0:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position. MG(16:0/0:0/0:0) is a minor component of olive oil and other vegetable oil.32899-41-53084463755422341519[H][C@](O)(CO)COC(=O)CCCCCCCCCCCCCCCC19H38O4InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3/t18-/m0/s1QHZLMUACJMDIAE-SFHVURJKSA-N(2S)-2,3-dihydroxypropyl hexadecanoate330.5026330.277009704-4.852(2S)-2,3-dihydroxypropyl hexadecanoate001-hexadecanoyl-rac-glycerol;1-monoacylglyceride;1-monoacylglycerol;1-palmitoyl-glycerol;Mag(16:0);Mag(16:0/0:0);Mg(16:0);Mg(16:0/0:0);A-monoacylglycerol;Alpha-monoacylglycerol;(2s)-1-o-hexadecanoylglycerol;(2s)-1-o-palmitoylglycerol;(s)-1-monopalmitin;(s)-2,3-dihydroxypropyl n-hexadecanoate;1-hexadecanoyl-sn-glycerol;Mg (16:0/0:0/0:0);Sn-1-palmitoylmonoglyceride;Sn-1-palmitoylmonoglycerol;(s)-2,3-dihydroxypropyl n-hexadecanoic acid;Glycerol 1-hexadecanoatePW_C007160MG16009218195923017012786151391Capric 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_C00039110:04299269451607785013212247212412503911812662529912820038885GlycerolHMDB0000131Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously.56-81-5C0011675317522GLYCEROL733DB04077OCC(O)COC3H8O3InChI=1S/C3H8O3/c4-1-3(6)2-5/h3-6H,1-2H2PEDCQBHIVMGVHV-UHFFFAOYSA-Npropane-1,2,3-triol92.093892.0473441221.103glycerol00FDB0007561,2,3-trihydroxypropane;Bulbold;Cristal;E 422;Emery 916;Glyceol opthalgan;Glycerin;Glycerine;Glyceritol;Glycerol;Glycyl alcohol;Glyrol;Glysanin;Ifp;Incorporation factor;Mackstat h 66;Osmoglyn;Pricerine 9091;Propanetriol;Rg-s;Trihydroxypropane;Tryhydroxypropane;1,2,3-propanetriol;Glycerolum;Glyzerin;Gro;OelsuessPW_C000085Ifp206382216153093962971086298107923217012545151424483184244931577903113780351117806411412122912612138912212143540912379944312394813512399313710658Glycerol-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.
LOA1292.3.1.5176811607690213779621091351888040917013818619610945Phosphatidic acid phosphohydrolase 1P32567
Mg(2+)-dependent phosphatidate (PA) phosphatase which catalyzes the dephosphorylation of PA to yield diacylglycerol. Required for de novo lipid synthesis and formation of lipid droplets. Controles transcription of phospholipid biosynthetic genes and nuclear structure by regulating the amount of membrane present at the nuclear envelope. Involved in plasmid maintenance, in respiration and in cell proliferation.
PAH1293.1.3.47793160779421013822121310946CTP-dependent diacylglycerol kinase 1Q12382
Involved in pre-tRNA splicing (By similarity). CTP-dependent diacylglycerol kinase that catalyzes the phosphorylation of diacylglycerol (DAG) to phosphatidate (PA). Controls phosphatidate levels at the nuclear envelope. Counteracts the activity of PAH1/SMP2. Involved in the resistance to nickel chloride and nalidixic acid. May be involved in vesicle trafficking between the endoplasmic reticulum and the Golgi apparatus.
DGK1292.7.1.174779216077952109141195914421311303Diacylglycerol O-acyltransferase 1Q08650Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis. Also has monoacylglycerol acyltransferase (MGAT) activity, catalyzing the acyl-CoA-dependent esterification of monoacylglycerol to diacylglycerol.DGA1292.3.1.20; 2.3.1.2292171951066918813822221311305Sterol esterase TGL1P34163
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo.
TGL1293.1.1.1392251701068118813822321311306Lipase 2P54857
Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids.
TGL2293.1.1.392261701068218813822421311307Lipase 3P40308
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process.
TGL3293.1.1.392271701068318813822521311308Lipase 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.
TGL4293.1.1.392281701068418813822621311309Lipase 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.
TGL5293.1.1.392291701068518813822721310954Lipase 3P40308
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process.
TGL3293.1.1.37739210923117013822821311310Monoglyceride lipaseP28321
Converts monoacylglycerides (MAG) to free fatty acids and glycerol. Required for efficient degradation of MAG, short-lived intermediates of glycerolipid metabolism which may also function as lipid signaling molecules. Controls inactivation of the signaling lipid N-palmitoylethanolamine (PEA).
YJU3293.1.1.2392331701382292134341Glycerol-3-phosphate O-acyltransferase 18PW_P004341114041065811405106594343Lysophosphatidate acyltransferase18PW_P004343114071066111408106621140910663114101066411411106654722Phosphatidic acid phosphohydrolase 118PW_P00472211905109454723CTP-dependent diacylglycerol kinase 118PW_P00472311906109465053Diacylglycerol O-acyltransferase 118PW_P00505312345113035055Triacylglycerol lipase complex18PW_P005055123471130512348113061234911307123501130812351113095056Diacylglycerol lipase18PW_P00505612352109545057Monoglyceride lipase18PW_P0050571235311310187432PW_R187432Right71013727421Compoundfalse710138811Compoundfalse71013910991Compoundfalse710140553621Compoundfalse17707943412.3.1.15187433PW_R187433Right710141553621Compoundfalse71014227421Compoundfalse710143555121Compoundfalse71014410991Compoundfalse17708043432.3.1.2325236falsePW_R025236Right81880555121Compoundfalse8188114201Compoundfalse81882433371Compoundfalse8188311041Compoundfalse2075147223.1.3.425237falsePW_R025237Right81884433371Compoundfalse81885571Compoundfalse81886555121Compoundfalse81887400341Compoundfalse8188811891Compoundfalse2075247232.7.1.174211717falsePW_R211717Right8132731083741Compoundfalse813274433371Compoundfalse81327510991Compoundfalse813276572821Compoundfalse20136850532.3.1.20211718falsePW_R211718Right813277572821Compoundfalse81327814201Compoundfalse813279400341Compoundfalse8132801083731Compoundfalse813281433371Compoundfalse20136950553.1.1.13211415falsePW_R211415Right811899433371Compoundfalse81190014201Compoundfalse811901400341Compoundfalse81190271601Compoundfalse8119033911Compoundfalse20106650563.1.1.3211416falsePW_R211416Right81190471601Compoundfalse81190514201Compoundfalse8119063911Compoundfalse811907400341Compoundfalse811908851Compoundfalse20106750573.1.1.23306995727422133false105531310regular1001003069958812133false92541310regular1001103069959109921385false138538510regular50303069960109921385false197552210regular50303069961109921385false273285510regular50303069962553622133false145042010regular100100306996327422133false158031510regular1001003069964555122133false205542210regular1001003069965142021349false222629710regular78783069966142021349false2526107010regular78783069967142021349false1876106710regular78783069968142021349false1346106910regular78783069969433372133false262542510regular1001003069970433372133false198096710regular1001003069971110421346false249333010regular44433069972572133false249556810regular10011030699734003421355false225167710regular787830699744003421355false211189210regular787830699754003421355false157689410regular787830699764003421355false105688610regular7878306997711892133false217556510regular10010030699781083742133false273057010regular1001203069979572822133false262797010regular10010030699801083732133false2105106710regular100120306998171602133false145596910regular10010030699823912133false1580106910regular10010030699833912133false1055106610regular1001003069984852133false93096410regular1001001181378106582132false11923908subunitregular150701181379106592132false11924358subunitregular150701181380106612132false17003858subunitregular150701181381106622132false18004558subunitregular150701181382106632132false17004908subunitregular150701181383106642132false18004108subunitregular150701181384106652132false17004358subunitregular150701181385109452132false23253908subunitregular150701181386109462132false23254858subunitregular150701181387113032132false26007158subunitregular150701181388113052132false23579668subunitregular150701181389113062132false235710168subunitregular150701181390113072132false22429368subunitregular150701181391113082132false22429868subunitregular150701181392113092132false224210368subunitregular150701181393109542132false17059888subunitregular150701181394113102132false11779858subunitregular15070930516434174672131177101118137811771021181379930517434374672131177103118138011771041181381117710511813821177106118138311771071181384930518472274672131177108118138593051947237467213117710911813869305205053746721311771101181387930521505574672131177111118138811771121181389117711311813901177114118139111771151181392930522505674672131177116118139393052350577467213117711711813944183456M1105 413 C1110 454 1162 470 1192 470 5false184183457M1025 468 C1055 468 1162 470 1192 470 5false184183458M1410 415 C1410 450 1372 470 1342 470 5false18trueM 861.9468550441649 197.26155629629605 L 847 196 L 853.3808877211858 209.57513432307834false4183459M1450 470 C1420 470 1372 470 1342 470 5false18trueM 861.9468550441649 197.26155629629605 L 847 196 L 853.3808877211858 209.57513432307834false4183460M1550 470 C1580 470 1670 470 1700 470 5false184183461M1630 415 C1630 441 1670 470 1700 470 5false184183462M2055 472 C2025 472 1880 470 1850 470 5false7trueM 1274.9468550441647 245.26155629629605 L 1260 244 L 1266.380887721186 257.5751343230783false4183463M2000 522 C2007 452 1880 470 1850 470 5false7trueM 1274.9468550441647 245.26155629629605 L 1260 244 L 1266.380887721186 257.5751343230783false4183464M2152 424 C2182 424 2295 425 2325 425 5false184183465M2265 375 C2274 407 2295 425 2325 425 5false184183466M2622 425 C2592 425 2505 425 2475 425 5false18trueM 1866.9468550441647 272.261556296296 L 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466.5751343230783false4183476M2677 970 C2677 940 2675 815 2675 785 5false18trueM 2100.9468550441647 454.261556296296 L 2086 453 L 2092.380887721186 466.5751343230783false4183477M2627 1020 C2597 1020 2422 1021 2392 1021 5false74183478M2565 1070 C2570 1004 2422 1021 2392 1021 5false74183479M2150 970 C2155 1009 2212 1021 2242 1021 5false18trueM 1866.9468550441647 796.261556296296 L 1852 795 L 1858.380887721186 808.5751343230784false4183480M2155 1067 C2153 1037 2212 1021 2242 1021 5false18trueM 1866.9468550441647 796.261556296296 L 1852 795 L 1858.380887721186 808.5751343230784false4183481M2080 1017 C2110 1017 2212 1021 2242 1021 5false18trueM 1866.9468550441647 796.261556296296 L 1852 795 L 1858.380887721186 808.5751343230784false4183482M1980 1017 C1950 1017 1885 1023 1855 1023 5false184183483M1915 1067 C1914 1030 1885 1023 1855 1023 5false184183484M1615 972 C1613 1012 1675 1023 1705 1023 5false18trueM 1254.9468550441647 759.261556296296 L 1240 758 L 1246.380887721186 771.5751343230784false4183485M1555 1019 C1585 1019 1675 1023 1705 1023 5false18trueM 1254.9468550441647 759.261556296296 L 1240 758 L 1246.380887721186 771.5751343230784false4183486M1630 1069 C1630 1024 1675 1023 1705 1023 5false18trueM 1254.9468550441647 759.261556296296 L 1240 758 L 1246.380887721186 771.5751343230784false4183487M1455 1019 C1425 1019 1357 1020 1327 1020 5false184183488M1385 1069 C1385 1033 1357 1020 1327 1020 5false184183489M1105 1066 C1107 1037 1147 1020 1177 1020 5false18trueM 889.9468550441649 695.261556296296 L 875 694 L 881.3808877211858 707.5751343230784false4183490M1095 964 C1100 991 1147 1020 1177 1020 5false18trueM 889.9468550441649 695.261556296296 L 875 694 L 881.3808877211858 707.5751343230784false4183491M1030 1014 C1060 1014 1147 1020 1177 1020 5false18trueM 889.9468550441649 695.261556296296 L 875 694 L 881.3808877211858 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569 C851 519 901 469 951 469 C1445 469 2088 469 2582 469 C2632 469 2682 519 2682 569 C2682 677 2682 818 2682 926 C2682 976 2632 1026 2582 1026 C2088 1026 1445 1026 951 1026 C901 1026 851 976 851 926 C851 818 851 677 851 569 91true61831.0557.0464332M226 326 C226 276 276 226 326 226 C1076 226 2050 226 2800 226 C2850 226 2900 276 2900 326 C2900 573 2900 894 2900 1141 C2900 1191 2850 1241 2800 1241 C2050 1241 1076 1241 326 1241 C276 1241 226 1191 226 1141 C226 894 226 573 226 326 1true62674.01015.0464333M126 227 C126 177 176 127 226 127 C1037 127 2090 127 2901 127 C2951 127 3001 177 3001 227 C3001 534 3001 932 3001 1239 C3001 1289 2951 1339 2901 1339 C2090 1339 1037 1339 226 1339 C176 1339 126 1289 126 1239 C126 932 126 534 126 227 1true62875.01212.086844715Endoplasmic Reticulum989653201.91.9160152784045956308254432708105239#FFEEDE41883609