13486PathwayTriacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z))In higher plants, the primary seed storage reserve is triacylglycerol rather than carbohydrates. Thus, triacylglycerol degradation is an important pathway from which plants obtain energy for growth. First, triacylglycerol lipase, an enzyme localized to the oil body (storage vacuole) membrane, catalyzes the conversion of a triglyceride into a 1,2-diglyceride. Second, the predicted enzyme diglyceride lipase (coloured orange in the image) is theorized to catalyze the conversion of a 1,2-diglyceride iinto a 2-acylglycerol. Third, a 2-acylglycerol is spontaneously converted into a 1-monoglyceride. Fourth, acylhydrolase catalyzes the conversion of a 1-monoglyceride into glycerol. Fifth, glycerol kinase catalyzes the conversion of glycerol into glycerol 3-phosphate. Sixth, glycerol-3-phosphate dehydrogenase (coloured dark green in the image), localized to the mitochondrial inner membrane, catalyzes the conversion of glycerol 3-phosphate into glycerone phosphate.MetabolicPW013681CenterPathwayVisualizationContext1396614933149#000099PathwayVisualization1343713486Triacylglycerol Degradation TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z))In higher plants, the primary seed storage reserve is triacylglycerol rather than carbohydrates. Thus, triacylglycerol degradation is an important pathway from which plants obtain energy for growth. First, triacylglycerol lipase, an enzyme localized to the oil body (storage vacuole) membrane, catalyzes the conversion of a triglyceride into a 1,2-diglyceride. Second, the predicted enzyme diglyceride lipase (coloured orange in the image) is theorized to catalyze the conversion of a 1,2-diglyceride iinto a 2-acylglycerol. Third, a 2-acylglycerol is spontaneously converted into a 1-monoglyceride. Fourth, acylhydrolase catalyzes the conversion of a 1-monoglyceride into glycerol. Fifth, glycerol kinase catalyzes the conversion of glycerol into glycerol 3-phosphate. Sixth, glycerol-3-phosphate dehydrogenase (coloured dark green in the image), localized to the mitochondrial inner membrane, catalyzes the conversion of glycerol 3-phosphate into glycerone phosphate.Metabolic45205Diacylglycerol and Triacylglycerol BiosynthesisSubPathway427830574Compound227917422303259Li-Beisson Y, Shorrosh B, Beisson F, Andersson MX, Arondel V, Bates PD, Baud S, Bird D, Debono A, Durrett TP, Franke RB, Graham IA, Katayama K, Kelly AA, Larson T, Markham JE, Miquel M, Molina I, Nishida I, Rowland O, Samuels L, Schmid KM, Wada H, Welti R, Xu C, Zallot R, Ohlrogge J: Acyl-lipid metabolism. Arabidopsis Book. 2010;8:e0133. doi: 10.1199/tab.0133. Epub 2010 Jun 11.13486Pathway917521477884Kim EY, Seo YS, Kim WT: AtDSEL, an Arabidopsis cytosolic DAD1-like acylhydrolase, is involved in negative regulation of storage oil mobilization during seedling establishment. J Plant Physiol. 2011 Sep 15;168(14):1705-9. doi: 10.1016/j.jplph.2011.03.004. Epub 2011 Apr 8.13486Pathway917614756771Eastmond PJ: Glycerol-insensitive Arabidopsis mutants: gli1 seedlings lack glycerol kinase, accumulate glycerol and are more resistant to abiotic stress. Plant J. 2004 Feb;37(4):617-25.13486Pathway917712586344Shen W, Wei Y, Dauk M, Zheng Z, Zou J: Identification of a mitochondrial glycerol-3-phosphate dehydrogenase from Arabidopsis thaliana: evidence for a mitochondrial glycerol-3-phosphate shuttle in plants. FEBS Lett. 2003 Feb 11;536(1-3):92-6.13486Pathway9178Taylor DC, Giblin EM, Reed DW, Hogge LR: Stereospecific analysis and mass spectrometry of triacylglycerols fromarabidopsis thaliana (L.) heynh. columbia seed. Journal Of The American Oil Chemists' Society. 1995 Mar 01;72(3):305-308. doi: 10.1007/BF02541087.13486Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404Cardiomyocyte CL:00007468Beta cellCL:00006397Epithelial CellCL:00000661Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote18Saccharomyces cerevisiae4932EukaryoteYeast4Arabidopsis thaliana3702EukaryoteThale cress23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote24Solanum lycopersicum4081EukaryoteTomato21Xenopus laevis8355EukaryoteAfrican clawed frog6Caenorhabditis elegans6239EukaryoteRoundworm25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia410Drosophila melanogaster7227EukaryoteFruit fly5CytoplasmGO:000573711Extracellular SpaceGO:00056156LysosomeGO:00057641CytosolGO:000582931Periplasmic SpaceGO:00056203Mitochondrial MatrixGO:000575914Mitochondrial Outer MembraneGO:00057412MitochondrionGO:000573915NucleusGO:00056344PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577835ChloroplastGO:000950712Mitochondrial Inner MembraneGO:000574332Inner MembraneGO:007025824Mitochondrial Intermembrane SpaceGO:000575836MembraneGO:001602053Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032519sarcoplasmic reticulumGO:001652916Lysosomal LumenGO:004320218Melanosome MembraneGO:003316225Golgi apparatusGO:000579420Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520240PeriplasmGO:00425972Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:0001102741128StomachBTO:0001307155264Adrenal 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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_C000085Ifp2063822161530939629710862981079232170125451514244831842449315779031137803511178064114121229126121389122121435409123799443123948135123993137414Adenosine triphosphateHMDB0000538Adenosine triphosphate (ATP) is a nucleotide consisting of a purine base (adenine) attached to the first carbon atom of ribose (a pentose sugar). Three phosphate groups are esterified at the fifth carbon atom of the ribose. ATP is incorporated into nucleic acids by polymerases in the processes of DNA replication and transcription. ATP contributes to cellular energy charge and participates in overall energy balance, maintaining cellular homeostasis. ATP can act as an extracellular signaling molecule via interactions with specific purinergic receptors to mediate a wide variety of processes as diverse as neurotransmission, inflammation, apoptosis, and bone remodelling. Extracellular ATP and its metabolite adenosine have also been shown to exert a variety of effects on nearly every cell type in human skin, and ATP seems to play a direct role in triggering skin inflammatory, regenerative, and fibrotic responses to mechanical injury, an indirect role in melanocyte proliferation and apoptosis, and a complex role in Langerhans cell-directed adaptive immunity. During exercise, intracellular homeostasis depends on the matching of adenosine triphosphate (ATP) supply and ATP demand. Metabolites play a useful role in communicating the extent of ATP demand to the metabolic supply pathways. Effects as different as proliferation or differentiation, chemotaxis, release of cytokines or lysosomal constituents, and generation of reactive oxygen or nitrogen species are elicited upon stimulation of blood cells with extracellular ATP. The increased concentration of adenosine triphosphate (ATP) in erythrocytes from patients with chronic renal failure (CRF) has been observed in many studies but the mechanism leading to these abnormalities still is controversial. (PMID: 15490415, 15129319, 14707763, 14696970, 11157473).56-65-5C00002595715422ATP5742DB00171NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H16N5O13P3InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1ZKHQWZAMYRWXGA-KQYNXXCUSA-N({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid507.181506.995745159-2.057adenosine triphosphate0-3FDB0218135'-(tetrahydrogen triphosphate) adenosine;5'-atp;Atp;Adenosine 5'-triphosphate;Adenosine 5'-triphosphorate;Adenosine 5'-triphosphoric acid;Adenosine triphosphate;Adenylpyrophosphorate;Adenylpyrophosphoric acid;Adephos;Adetol;Adynol;Atipi;Atriphos;Cardenosine;Fosfobion;Glucobasin;Myotriphos;Phosphobion;Striadyne;Triadenyl;Triphosphaden;Triphosphoric acid adenosine ester;Adenosine-5'-triphosphate;H4atp;Adenosine triphosphoric acid;Adenosine-5'-triphosphoric acidPW_C000414ATP9221460826616414224781373332799593439976321051821121021464921561421605824055924342727264628122930296631637236166136175143992344743147689148645450328950352651557520597521510052501045291101531311153461125390103540611754301185443120554212955561325569133560313556211085846143585414658761075897147592415160481556109161623016664931786839188687016069761997157205718420672092107225213722921172981987302216739021774082187432163748122274991908186225118472771190317012010281120391641217828512578226126912901326422315327308423263154262132242694318770282537721813477233329774683337763233678037332780413507816812878214351782403537841133578494115788501307886533178919334800283688004618480674119856291948261241132349411328238811628010911991412211999240612015440712024538212036241212124642912139212312139743312147140812197441012206512512207938312208340512240242212244443512291939912300944612381646412395144712395646812402937412452744412461613612463039812463437612494347212497237512501147012530429712537147912539229912551548112559548412612348512622030012623449512624047812654749112659649912691350112712338912773151612778139512779639012780120912811950812816751781Glycerol 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_C000081Glyc1P104381475214884221155862951076296108841216291221701065318812546151125502231531924934814174246631842467315780301117805235078372345783781327995213481808253938261249478938411055338811063639111584011812075612212129741812134512112141543312335313512386745412397446812578829712597848912599129912724320512743150640034Hydrogen 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+2154670875315788318483111621463261464542231492780174250224254424547104576184694705241103532711153531125626108563910756991005720105574211759631476037155607015760931616130159623216664831786601152669210168431886910187710016371682057191206745321974542207472222752521375322107558212757216075901708195225821815182432268413162842022491391959155249119151641201528112181285122462861226628712521227132572231332529415330308423293154235431842401322424053124245432076912293771361337721013477372331778041147795513277990327779913477837934579929130800193688038731080388304807221199382312494823383110550388112855941132803901155373981155391181158563361162051091199734061201934071205491221205934091211704241211714251225694181226153841226871251227581201231831351232181371237424591237434601251414541251881211252731361253594791255504811257304831257362971258092991265174951267174891267664801268233001269025011272132081283085061283613911284303951034Adenosine diphosphateHMDB0001341Adenosine diphosphate, abbreviated ADP, is a nucleotide. It is an ester of pyrophosphoric acid with the nucleotide adenine. ADP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase adenine. ADP is the product of ATP dephosphorylation by ATPases. ADP is converted back to ATP by ATP synthases.58-64-0C00008602216761ADP5800NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1OC10H15N5O10P2InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1XTWYTFMLZFPYCI-KQYNXXCUSA-N[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid427.2011427.029414749-2.126adenosine-diphosphate0-2FDB021817Adp;Adenosindiphosphorsaeure;Adenosine 5'-pyrophosphate;Adenosine diphosphate;Adenosine pyrophosphate;Adenosine-5'-diphosphate;Adenosine-5-diphosphate;Adenosine-diphosphate;5'-adenylphosphoric acid;Adenosine 5'-diphosphate;H3adp;5'-adenylphosphate;Adenosine 5'-diphosphoric acid;Adenosine-5'-diphosphoric acidPW_C001034ADP23413484152248213801596315978310611415182190149210418211310216158240859243527272847273646285529316572363561440023447631477091503626515775208975217100531511153491125392103544612055441295572133562410857411175764101584914358561465878107589914759261516050155611116162311666495178670094684118868721607159205718720672082107226213723121173001987303216739121774102187433163748322281872251185127711905170120132811218028513262223153293084232831542398313426223224269631877029253770871327721613477306329774723337766333678039332780433507817012878215351782443537841433578495115787053317884913078920334800303688062211880651135806761199482712411328338811620410911994412211999440612015640712031838212036641212124842912139412312139943312147240812189938312197641012206412512208540512240542212244543512297339912301344612381846412395344712395846812403037412445239812452944412461513612463637612494747212497537512501247012533429712537347912549229912551748112564548412612548512621930012623549512624247812655049112659749912691550112773351612778039512779739012780320912812250812816851712831338942631Glycerone phosphateDihydroxyacetone phosphate dilithium salt 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 dilithium salt is soluble (in water) and a moderately acidic compound (based on its pKa).[Li+].[Li+].OCC(=O)COP([O-])([O-])=OC3H5Li2O6PInChI=1S/C3H7O6P.2Li/c4-1-3(5)2-9-10(6,7)8;;/h4H,1-2H2,(H2,6,7,8);;/q;2*+1/p-2QWIKESRFRWLYIA-UHFFFAOYSA-Ldilithium(1+) ion 1-hydroxy-3-(phosphonatooxy)propan-2-one181.924182.014382502-0.701dilithium(1+) ion dihydroxyacetone phosphate0-2PW_C042631GlyPhop12547223129142223271DG(18:1(9Z)/18:3(6Z,9Z,12Z)/0:0)HMDB0007220DG(18:1(9Z)/18:3(6Z,9Z,12Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(18:1(9Z)/18:3(6Z,9Z,12Z)/0:0), in particular, consists of one chain of oleic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the g-linolenic acid moiety is derived from animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.C0016514275403DIACYLGLYCEROL24765997[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCCC39H68O5InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,17-20,24,26,37,40H,3-11,13,15-16,21-23,25,27-36H2,1-2H3/b14-12-,19-17-,20-18-,26-24-/t37-/m0/s1MMKHFCYHSNLQRO-MICHFLGGSA-N(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate616.9542616.506675286-7.571diacylglycerol00FDB0244131-oleoyl-2-g-linolenoyl-sn-glycerol;1-oleoyl-2-gamma-linolenoyl-sn-glycerol;Dag(18:1/18:3);Dag(18:1n9/18:3n6);Dag(18:1w9/18:3w6);Dag(36:4);Dg(18:1/18:3);Dg(18:1n9/18:3n6);Dg(18:1w9/18:3w6);Dg(36:4);Diacylglycerol;Diacylglycerol(18:1/18:3);Diacylglycerol(18:1n9/18:3n6);Diacylglycerol(18:1w9/18:3w6);Diacylglycerol(36:4);DiglyceridePW_C003271DG36:41307215117081498124528584826331986553831151163901177203981420WaterHMDB0002111Water 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_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765137136MG(0:0/18:3(6Z,9Z,12Z)/0:0)HMDB0011539MG(0:0/18:3(6Z,9Z,12Z)/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.116460449820783[H]C(CO)(CO)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCCC21H36O4InChI=1S/C21H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-20(18-22)19-23/h6-7,9-10,12-13,20,22-23H,2-5,8,11,14-19H2,1H3/b7-6-,10-9-,13-12-BXAXVVVVPFELOK-QNEBEIHSSA-N1,3-dihydroxypropan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate352.5081352.26135964-4.9021,3-dihydroxypropan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate001-monoacylglyceride;1-monoacylglycerol;2-(6z,9z,12z-octadecatrienoyl)-rac-glycerol;2-g-linolenoyl-glycerol;2-gamma-linolenoyl-glycerol;Mag(0:0/18:3);Mag(0:0/18:3n6);Mag(0:0/18:3w6);Mag(18:3);Mg(0:0/18:3);Mg(0:0/18:3n6);Mg(0:0/18:3w6);Mg(18:3);B-monoacylglycerol;Beta-monoacylglycerolPW_C007136MG18:312956151133Oleic acidHMDB0000207Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. (Stedman, 26th ed) Biological Source: Major constituent of plant oils e.g. olive oil (about 80%), almond oil (about 80%) and many others, mainly as glyceride. Constituent of tall oil and present in fruits Use/Importance: Food additive. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. Emulsifying agent in foods and pharmaceuticals. Biological Use/Importance: Skin penetrant. Herbicide, insecticide, fungicide (Dictionary of Organic Compounds). Oleic acid is a fatty acid that occurs naturally in various animal and vegetable fats and oils. It is an odorless, colourless oil, although commercial samples may be yellowish. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the oil that is predominantly composed of oleic acid. (Wiki).112-80-1C0071244563916196OLEATE-CPD393217CCCCCCCC\C=C/CCCCCCCC(O)=OC18H34O2InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-ZQPPMHVWECSIRJ-KTKRTIGZSA-N(9Z)-octadec-9-enoic acid282.4614282.255880332-6.371oleic acid0-1FDB012858(9z)-9-octadecenoate;(9z)-9-octadecenoic acid;(9z)-octadecenoate;(9z)-octadecenoic acid;(z)-9-octadecanoate;(z)-9-octadecanoic acid;(z)-octadec-9-enoate;(z)-octadec-9-enoic acid;9,10-octadecenoate;9,10-octadecenoic acid;9-(z)-octadecenoate;9-(z)-octadecenoic acid;9-octadecenoate;9-octadecenoic acid;Century cd fatty acid;Distoline;Emersol 210;Emersol 211;Emersol 213;Emersol 220 white oleate;Emersol 220 white oleic acid;Emersol 221 low titer white oleate;Emersol 221 low titer white oleic acid;Emersol 233ll;Emersol 6321;Emersol 6333 nf;Emersol 7021;Glycon ro;Glycon wo;Groco 2;Groco 4;Groco 5l;Groco 6;Industrene 104;Industrene 105;Industrene 205;Industrene 206;L'acide oleique;Metaupon;Oelsauere;Oleate;Oleic acid extra pure;Oleinate;Oleinic acid;Pamolyn;Pamolyn 100;Pamolyn 100 fg;Pamolyn 100 fgk;Pamolyn 125;Priolene 6900;Red oil;Tego-oleic 130;Vopcolene 27;Wecoline oo;Z-9-octadecenoate;Z-9-octadecenoic acid;Cis-9-octadecenoate;Cis-9-octadecenoic acid;Cis-octadec-9-enoate;Cis-octadec-9-enoic acid;Cis-oleate;Cis-oleic acid;18:1 n-9;18:1delta9cis;C18:1 n-9;Cis-delta(9)-octadecenoic acid;Octadec-9-enoic acid;Oelsaeure;Cis-delta(9)-octadecenoate;Cis-δ(9)-octadecenoate;Cis-δ(9)-octadecenoic acid;Octadec-9-enoate;FA(18:1(9Z))PW_C000133Oleate129171517165MG(18:3(6Z,9Z,12Z)/0:0/0:0)HMDB0011569MG(18:3(6Z,9Z,12Z)/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.5348097824765788[H][C@](O)(CO)COC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCCC21H36O4InChI=1S/C21H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h6-7,9-10,12-13,20,22-23H,2-5,8,11,14-19H2,1H3/b7-6-,10-9-,13-12-/t20-/m0/s1XQBHBEXBUZDCRY-FFXVNFNPSA-N(2S)-2,3-dihydroxypropyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate352.5081352.26135964-4.982(2S)-2,3-dihydroxypropyl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate001-(6z,9z,12z-octadecatrienoyl)-rac-glycerol;1-monoacylglyceride;1-monoacylglycerol;1-g-linolenoyl-glycerol;1-gamma-linolenoyl-glycerol;Mag(18:3);Mag(18:3/0:0);Mag(18:3n6/0:0);Mag(18:3w6/0:0);Mg(18:3);Mg(18:3/0:0);Mg(18:3n6/0:0);Mg(18:3w6/0:0);A-monoacylglycerol;Alpha-monoacylglycerolPW_C007165MG18:3129571511772γ-Linolenic acidHMDB0003073Gamma-Linolenic acid is an omega-6 fatty acid produced in the body as the delta 6-desaturase metabolite of linoleic acid. It is converted to dihomo-gamma-linolenic acid, a biosynthetic precursor of monoenoic prostaglandins such as PGE1. (From Merck Index, 11th ed) -- Pubchem.506-26-3C064265280933286615Z13E-15S-91115-TRIHYDROXYPROSTA-4444436CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=OC18H30O2InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,12-13H,2-5,8,11,14-17H2,1H3,(H,19,20)/b7-6-,10-9-,13-12-VZCCETWTMQHEPK-QNEBEIHSSA-N(6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid278.4296278.224580204-6.041gamma linolenic acid0-1FDB002943(6,9,12)-linolenate;(6,9,12)-linolenic acid;(6z,9z,12z)-octadecatrienoate;(6z,9z,12z)-octadecatrienoic acid;(z,z,z)-6,9,12-octadecatrienoate;(z,z,z)-6,9,12-octadecatrienoic acid;6(z),9(z),12(z)-octadecatrienoate;6(z),9(z),12(z)-octadecatrienoic acid;6,9,12-all-cis-octadecatrienoate;6,9,12-all-cis-octadecatrienoic acid;6,9,12-octadecatrienoate;6,9,12-octadecatrienoic acid;6z,9z,12z-octadecatrienoate;6z,9z,12z-octadecatrienoic acid;All-cis-6,9,12-octadecatrienoate;All-cis-6,9,12-octadecatrienoic acid;Ligla;Cis-delta(6,9,12)-octadecatrienoate;Cis-delta(6,9,12)-octadecatrienoic acid;Gamma-linolenate;Gamma-linolenic acid;Gamma-llnolenic acid;18:3 (n-6);6-cis,9-cis,12-cis-octadecatrienoic acid;C18:3 (n-6);C18:3, n-6,9,12 all-cis;Gamma-linolensaeure;Gamoleic acid;Gamolenic acid;Gla;Octadeca-6,9,12-triensaeure;(6z,9z,12z)-octadeca-6,9,12-trienoate;6-cis,9-cis,12-cis-octadecatrienoate;Cis-δ(6,9,12)-octadecatrienoate;Cis-δ(6,9,12)-octadecatrienoic acid;G-linolensaeure;γ-linolensaeure;Gamoleate;Gamolenate;FA(18:3(6Z,9Z,12Z))PW_C001772g-Lina28418129211517726813012020812512288513612556230012709339530574TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z))HMDB0050021TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)) is a dioleic acid triglyceride. Triglycerides (TGs or TAGs) are also known as triacylglycerols or triacylglycerides, meaning that they are glycerides in which the glycerol is esterified with three fatty acid groups (i.e. fatty acid trimesters of glycerol). TGs may be divided into three general types with respect to their acyl substituents. They are simple or monoacid if they contain only one type of fatty acid, diacid if they contain two types of fatty acids and triacid if three different acyl groups. Chain lengths of the fatty acids in naturally occurring triglycerides can be of varying lengths and saturations but 16, 18 and 20 carbons are the most common. TG(18:1(9Z)/18:3(6Z,9Z,12Z)/18:1(9Z)), in particular, consists of one chain of oleic acid at the C-1 position, one chain of g-linolenic acid at the C-2 position and one chain of oleic acid at the C-3 position. TGs are the main constituent of vegetable oil and animal fats. TGs are major components of very low density lipoprotein (VLDL) and chylomicrons, play an important role in metabolism as energy sources and transporters of dietary fat. They contain more than twice the energy (9 kcal/g) of carbohydrates and proteins. In the intestine, triglycerides are split into glycerol and fatty acids (this process is called lipolysis) with the help of lipases and bile secretions, which can then move into blood vessels. The triglycerides are rebuilt in the blood from their fragments and become constituents of lipoproteins, which deliver the fatty acids to and from fat cells among other functions. Various tissues can release the free fatty acids and take them up as a source of energy. Fat cells can synthesize and store triglycerides. When the body requires fatty acids as an energy source, the hormone glucagon signals the breakdown of the triglycerides by hormone-sensitive lipase to release free fatty acids. As the brain cannot utilize fatty acids as an energy source, the glycerol component of triglycerides can be converted into glucose for brain fuel when it is broken down. (www.cyberlipid.org, www.wikipedia.org)<br />TAGs can serve as fatty acid stores in all cells, but primarily in adipocytes of adipose tissue. The major building block for the synthesis of triacylglycerides, in non-adipose tissue, is glycerol. Adipocytes lack glycerol kinase and so must use another route to TAG synthesis. Specifically, dihydroxyacetone phosphate (DHAP), which is produced during glycolysis, is the precursor for TAG synthesis in adipose tissue. DHAP can also serve as a TAG precursor in non-adipose tissues, but does so to a much lesser extent than glycerol. The use of DHAP for the TAG backbone depends on whether the synthesis of the TAGs occurs in the mitochondria and ER or the ER and the peroxisomes. The ER/mitochondria pathway requires the action of glycerol-3-phosphate dehydrogenase to convert DHAP to glycerol-3-phosphate. Glycerol-3-phosphate acyltransferase then esterifies a fatty acid to glycerol-3-phosphate thereby generating lysophosphatidic acid. The ER/peroxisome reaction pathway uses the peroxisomal enzyme DHAP acyltransferase to acylate DHAP to acyl-DHAP which is then reduced by acyl-DHAP reductase. The fatty acids that are incorporated into TAGs are activated to acyl-CoAs through the action of acyl-CoA synthetases. Two molecules of acyl-CoA are esterified to glycerol-3-phosphate to yield 1,2-diacylglycerol phosphate (also known as phosphatidic acid). The phosphate is then removed by phosphatidic acid phosphatase (PAP1), to generate 1,2-diacylglycerol. This diacylglycerol serves as the substrate for addition of the third fatty acid to make TAG. Intestinal monoacylglycerols, derived from dietary fats, can also serve as substrates for the synthesis of 1,2-diacylglycerols.30777943[H]C(COC(=O)CCCCCCC\C=C/CCCCCCCC)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/CCCCCC57H100O6InChI=1S/C57H100O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h18,21,25-30,36,39,54H,4-17,19-20,22-24,31-35,37-38,40-53H2,1-3H3/b21-18-,28-25-,29-26-,30-27-,39-36-JMHHDSQNLZCCLT-YPDKBCJXSA-N1,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate881.4003880.751990932-8.1601,3-bis[(9Z)-octadec-9-enoyloxy]propan-2-yl (6Z,9Z,12Z)-octadeca-6,9,12-trienoate001-(9z-octadecenoyl)-2-(6z,9z,12z-octadecatrienoyl)-3-(9z-octadecenoyl)-glycerol;1-oleoyl-2-g-linolenoyl-3-oleoyl-glycerol;Tag(18:1/18:3/18:1);Tag(54:5);Tg(18:1/18:3/18:1);Tg(54:5);Tracylglycerol(18:1/18:3/18:1);Tracylglycerol(54:5);Triacylglycerol;TriglyceridePW_C030574TG54:513071227137741513239649231an electron-transfer quinoneCompound1860CompoundPW_EC000231Quinone232electron-transfer quinolCompound41682CompoundPW_EC000232Quinol11604Glycerol kinaseQ9M8L4Glycerol kinase is an enzyme in the cytosol that catalyzes a reaction in the triacylglycerol degradation pathway whereby glycerol is converted into glycerol 3-phosphate.GLPK42.7.1.301254115111605Glycerol-3-phosphate dehydrogenaseQ9SS48Glycerol-3-phosphate dehydrogenase is an enzyme localized to the mitochondrial inner membrane that catalyzes a reaction in the triacylglycerol degradation pathway whereby glycerol 3-phosphate is converted into glycerone phosphate.SDP641.1.5.312543223129152229659UnknownUnknown45.4.99.-; 4.2.1.-59301517466222749022374942248171225927222180962253809633798096438013660729313704569313705124911603AcylhydrolaseO49523Acylhydrolase is an enzyme in the cytosol that catalyzes a reaction in the triacylglycerol degradation pathway whereby a 1-monoglyceride is converted into glycerol.DSEL43.1.1.231253915111601Triacylglycerol lipaseQ9LZA6Triacylglycerol lipase is an enzyme localized to the oil body (storage vacuole) membrane that catalyzes a reaction in the triacylglycerol degradation pathway whereby a triglyceride is converted into a 1,2-diglyceride.SDP143.1.1.31253522712783151129132265482Glycerol kinase4PW_P0054821283611604125421515483Glycerol-3-phosphate dehydrogenase4PW_P0054831283711605125442235480Diglyceride lipase4PW_P005480128349659125381515481Acylhydrolase4PW_P0054811283511603125401515479Triacylglycerol lipase4PW_P0054791283311601125362275484Glycerol 3-phosphate transporter4PW_P0054841283896591254922347599PW_R047599Both147271851Compoundfalse1472724141Compoundfalse147273811Compoundfalse147274400341Compoundfalse14727510341Compoundfalse3774054822.7.1.3047600PW_R047600Right147276811Compoundfalse1472772311ElementCollectionfalse147278426311Compoundfalse1472792321ElementCollectionfalse3774154831.1.5.347948PW_R047948Right14888632711Compoundfalse14888714201Compoundfalse14888871361Compoundfalse148889400341Compoundfalse1488901331Compoundfalse3807854803.1.1.34/3.1.1.7947903truePW_R047903Right14867071361Compoundfalse14867171651Compoundfalse47904PW_R047904Right14867271651Compoundfalse14867314201Compoundfalse14867417721Compoundfalse148675400341Compoundfalse148676851Compoundfalse3803654813.1.1.2347947PW_R047947Right148881305741Compoundfalse14888214201Compoundfalse148883400341Compoundfalse14888432711Compoundfalse1488851331Compoundfalse3807754793.1.1.3901PW_T0009011053811Compound151223Right80154842017-02-25T16:30:50-07:002017-02-25T16:30:50-07:00223434021851513false225041910regular10010043402241415142false234533910regular5030434023811513false270041710regular100110434024812233false2700102210regular1001104340254003415155false265157210regular78784340264003415155false14512968regular78784340274003415155false220129610regular78784340284003415155false100130210regular7878434029103415143false265034510regular5030434030426312233false180091210regular10011043403132711513false105042510regular100100434032142015149false11262978regular7878434033142015149false187129810regular7878434034142015149false67130110regular787843403571361513false150042110regular1001004340361331513false145057410regular10010043403771651513false180042110regular10010043403817721513false220057110regular100110434039305741513false60042610regular1001004340401331513false100057510regular100100524323137223false2200107212regular10090524423237223false1850107212regular10090255675116041512false24454368subunitregular150702556761160522399false20009348subunitregular15070255677965915198false12504406proteinregular15070255678116031512false20004368subunitregular150702556791160115199false8004408subunitregular15070255680965976false26759078proteinregular15070147894548213437151254851255675147895548313437223254852255676147896548013437151254853255677147897548113437151254854255678147898547913437151254855255679147899548413437254856255680668255M2350 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