83PathwayGlycerolipid MetabolismThe glycerolipid metabolism pathway describes the synthesis of glycerolipids such as monoacylglycerols (MAGs), diacylglycerols (DAGs), triacylglycerols (TAGs), phosphatidic acids (PAs), and lysophosphatidic acids (LPAs). The process begins with cytoplasmic 3-phosphoglyceric acid (a product of glycolysis). This molecule is dephosphorylated via the enzyme glycerate kinase to produce glyceric acid. Glyceric acid is then transformed to glycerol (via the action of aldehyde dehydrogenase and aldose reductase). The free, cytoplasmic glycerol can then be phosphorylated to glycerol-3-phosphate through the action of glycerol kinase. Glycerol-3-phosphate can then enter the endoplasmic reticulum where glycerol-3-phosphate acyltransferase (GPAT) may combine various acyl-CoA moieties (which donate acyl groups) to form lysophosphatidic (LPA) or phosphatidic acid (PA). The resulting phosphatidic acids can be dephosphorylated via lipid phosphate phosphohydrolase (also known as phosphatidate phosphatase) to produce diacylglycerols (DAGs). The resulting DAGs can be converted into triacylglycerols (TAGs) via the addition of another acyl group (contributed via acyl-CoA) and the action of 1-acyl-sn-glycerol-3-phosphate acyltransferase. Extracellularly, the triacylglycerols (TAGs) can be converted to monoacylglycerols (MAGs) through the action of hepatic triacylglycerol lipase. In addition to this cytoplasmic route of glycerolipid synthesis, another route via mitochondrial synthesis also exists. This route begins with glycerol-3-phosphate, which can be either derived from dihydroxyacetone phosphate (DHAP), a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells) or from glycerol itself. Glycerol-3-phosphate in the mitochondria is first acylated via acyl-coenzyme A (acyl-CoA) through the action of mitochondrial glycerol-3-phosphate acyltransferase to form lysophosphatidic acid (LPA). Once synthesized, lysophosphatidic acid is then acylated with another molecule of acyl-CoA via the action of 1-acyl-sn-glycerol-3-phosphate acetyltransferase to yield phosphatidic acid. Phosphatidic acid is then dephosphorylated to form diacylglycerol. Specifically, diacylglycerol is formed by the action of phosphatidate phosphatase (also known as lipid phosphate phosphohydrolase) on phosphatidic acid coupled with the release of a phosphate. The phosphatase exists as 3 isozymes. Diacylglycerol is a precursor to triacylglycerol (triglyceride), which is formed in the addition of a third fatty acid to the diacylglycerol by the action of diglyceride acyltransferase. Since diacylglycerol is synthesized via phosphatidic acid, it 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. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. Fatty acids, stored as triglycerides in humans, are an important and a particularly rich source of energy. The energy yield from a gram of fatty acids is approximately 9 kcal/g (39 kJ/g), compared to 4 kcal/g (17 kJ/g) for carbohydrates. Since the hydrocarbon portion of fatty acids is hydrophobic, these molecules can be stored in a relatively anhydrous (water-free) environment. Fatty acids can hold more than six times the amount of energy than sugars on a weight basis. In other words, if you relied on sugars or carbohydrates to store energy, then you would need to carry 67.5 lb (31 kg) of glycogen to have the energy equivalent to 10 lb (5 kg) of fat.MetabolicPW000144CenterPathwayVisualizationContext15947003300#000099PathwayVisualization8783Glycerolipid MetabolismThe glycerolipid metabolism pathway describes the synthesis of glycerolipids such as monoacylglycerols (MAGs), diacylglycerols (DAGs), triacylglycerols (TAGs), phosphatidic acids (PAs), and lysophosphatidic acids (LPAs). The process begins with cytoplasmic 3-phosphoglyceric acid (a product of glycolysis). This molecule is dephosphorylated via the enzyme glycerate kinase to produce glyceric acid. Glyceric acid is then transformed to glycerol (via the action of aldehyde dehydrogenase and aldose reductase). The free, cytoplasmic glycerol can then be phosphorylated to glycerol-3-phosphate through the action of glycerol kinase. Glycerol-3-phosphate can then enter the endoplasmic reticulum where glycerol-3-phosphate acyltransferase (GPAT) may combine various acyl-CoA moieties (which donate acyl groups) to form lysophosphatidic (LPA) or phosphatidic acid (PA). The resulting phosphatidic acids can be dephosphorylated via lipid phosphate phosphohydrolase (also known as phosphatidate phosphatase) to produce diacylglycerols (DAGs). The resulting DAGs can be converted into triacylglycerols (TAGs) via the addition of another acyl group (contributed via acyl-CoA) and the action of 1-acyl-sn-glycerol-3-phosphate acyltransferase. Extracellularly, the triacylglycerols (TAGs) can be converted to monoacylglycerols (MAGs) through the action of hepatic triacylglycerol lipase. In addition to this cytoplasmic route of glycerolipid synthesis, another route via mitochondrial synthesis also exists. This route begins with glycerol-3-phosphate, which can be either derived from dihydroxyacetone phosphate (DHAP), a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells) or from glycerol itself. Glycerol-3-phosphate in the mitochondria is first acylated via acyl-coenzyme A (acyl-CoA) through the action of mitochondrial glycerol-3-phosphate acyltransferase to form lysophosphatidic acid (LPA). Once synthesized, lysophosphatidic acid is then acylated with another molecule of acyl-CoA via the action of 1-acyl-sn-glycerol-3-phosphate acetyltransferase to yield phosphatidic acid. Phosphatidic acid is then dephosphorylated to form diacylglycerol. Specifically, diacylglycerol is formed by the action of phosphatidate phosphatase (also known as lipid phosphate phosphohydrolase) on phosphatidic acid coupled with the release of a phosphate. The phosphatase exists as 3 isozymes. Diacylglycerol is a precursor to triacylglycerol (triglyceride), which is formed in the addition of a third fatty acid to the diacylglycerol by the action of diglyceride acyltransferase. Since diacylglycerol is synthesized via phosphatidic acid, it 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. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. Fatty acids, stored as triglycerides in humans, are an important and a particularly rich source of energy. The energy yield from a gram of fatty acids is approximately 9 kcal/g (39 kJ/g), compared to 4 kcal/g (17 kJ/g) for carbohydrates. Since the hydrocarbon portion of fatty acids is hydrophobic, these molecules can be stored in a relatively anhydrous (water-free) environment. Fatty acids can hold more than six times the amount of energy than sugars on a weight basis. In other words, if you relied on sugars or carbohydrates to store energy, then you would need to carry 67.5 lb (31 kg) of glycogen to have the energy equivalent to 10 lb (5 kg) of fat.Metabolic116476SubPathway259644Compound216510SubPathway260145Compound294Lehninger, A.L. Lehninger principles of biochemistry (4th ed.) (2005). New York: W.H Freeman.83Pathway95Salway, J.G. Metabolism at a glance (3rd ed.) (2004). Alden, Mass.: Blackwell Pub.83Pathway96Vance, D.E., and Vance, J.E. Biochemistry of lipids, lipoproteins, and membranes (4th ed.) (2002) Amsterdam; Boston: Elsevier.83Pathway28044228411173Zhang P, Reue K: Lipin proteins and glycerolipid metabolism: Roles at the ER membrane and beyond. Biochim Biophys Acta Biomembr. 2017 Sep;1859(9 Pt B):1583-1595. doi: 10.1016/j.bbamem.2017.04.007. Epub 2017 Apr 11.83Pathway28044316905614Kiessling V, Crane JM, Tamm LK: Transbilayer effects of raft-like lipid domains in asymmetric planar bilayers measured by single molecule tracking. Biophys J. 2006 Nov 1;91(9):3313-26. doi: 10.1529/biophysj.106.091421. Epub 2006 Aug 11.83Pathway2804447961664Rusinol AE, Cui Z, Chen MH, Vance JE: A unique mitochondria-associated membrane fraction from rat liver has a high capacity for lipid synthesis and contains pre-Golgi secretory proteins including nascent lipoproteins. J Biol Chem. 1994 Nov 4;269(44):27494-502.83Pathway28044517389595Nagle CA, An J, Shiota M, Torres TP, Cline GW, Liu ZX, Wang S, Catlin RL, Shulman GI, Newgard CB, Coleman RA: Hepatic overexpression of glycerol-sn-3-phosphate acyltransferase 1 in rats causes insulin resistance. J Biol Chem. 2007 May 18;282(20):14807-15. doi: 10.1074/jbc.M611550200. Epub 2007 Mar 27.83Pathway28044611807558Helenius J, Ng DT, Marolda CL, Walter P, Valvano MA, Aebi M: Translocation of lipid-linked oligosaccharides across the ER membrane requires Rft1 protein. Nature. 2002 Jan 24;415(6870):447-50. doi: 10.1038/415447a.83Pathway28044716498400Alaimo C, Catrein I, Morf L, Marolda CL, Callewaert N, Valvano MA, Feldman MF, Aebi M: Two distinct but interchangeable mechanisms for flipping of lipid-linked oligosaccharides. EMBO J. 2006 Mar 8;25(5):967-76. doi: 10.1038/sj.emboj.7601024. Epub 2006 Feb 23.83Pathway28044818216768van Meer G, Voelker DR, Feigenson GW: Membrane lipids: where they are and how they behave. Nat Rev Mol Cell Biol. 2008 Feb;9(2):112-24. doi: 10.1038/nrm2330.83Pathway28044915823040Baumann NA, Sullivan DP, Ohvo-Rekila H, Simonot C, Pottekat A, Klaassen Z, Beh CT, Menon AK: Transport of newly synthesized sterol to the sterol-enriched plasma membrane occurs via nonvesicular equilibration. Biochemistry. 2005 Apr 19;44(15):5816-26. doi: 10.1021/bi048296z.83Pathway28045117098933Sud M, Fahy E, Cotter D, Brown A, Dennis EA, Glass CK, Merrill AH Jr, Murphy RC, Raetz CR, Russell DW, Subramaniam S: LMSD: LIPID MAPS structure database. Nucleic Acids Res. 2007 Jan;35(Database issue):D527-32. doi: 10.1093/nar/gkl838. Epub 2006 Nov 10.83Pathway28045222345606Henry 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.111.130286.83Pathway28045311751875Oelkers P, Cromley D, Padamsee M, Billheimer JT, Sturley SL: The DGA1 gene determines a second triglyceride synthetic pathway in yeast. J Biol Chem. 2002 Mar 15;277(11):8877-81. doi: 10.1074/jbc.M111646200. Epub 2001 Dec 18.83Pathway28045420972264Gaspar ML, Hofbauer HF, Kohlwein SD, Henry SA: Coordination of storage lipid synthesis and membrane biogenesis: evidence for cross-talk between triacylglycerol metabolism and phosphatidylinositol synthesis. J Biol Chem. 2011 Jan 21;286(3):1696-708. doi: 10.1074/jbc.M110.172296. Epub 2010 Oct 23.83Pathway28045516777854Gaspar ML, Aregullin MA, Jesch SA, Henry SA: Inositol induces a profound alteration in the pattern and rate of synthesis and turnover of membrane lipids in Saccharomyces cerevisiae. J Biol Chem. 2006 Aug 11;281(32):22773-85. doi: 10.1074/jbc.M603548200. Epub 2006 Jun 15.83Pathway28045618614533Gaspar ML, Jesch SA, Viswanatha R, Antosh AL, Brown WJ, Kohlwein SD, Henry SA: A block in endoplasmic reticulum-to-Golgi trafficking inhibits phospholipid synthesis and induces neutral lipid accumulation. J Biol Chem. 2008 Sep 12;283(37):25735-51. doi: 10.1074/jbc.M802685200. Epub 2008 Jul 9.83Pathway1CellCL:00000002Platelet CL:00002335HepatocyteCL:00001823NeuronCL:00005404CardiomyocyteCL:00007468Beta cellCL:00006397Epithelial CellCL:000006611Colorectal Cancer CellCL:00010641Homo sapiens9606EukaryoteHuman3Escherichia coli562Prokaryote24Solanum lycopersicum4081EukaryoteTomato4Arabidopsis thaliana3702EukaryoteThale cress18Saccharomyces cerevisiae4932EukaryoteYeast23Pseudomonas aeruginosa287Prokaryote12Mus musculus10090EukaryoteMouse5Bos taurus9913EukaryoteCattle17Rattus norvegicus10116EukaryoteRat10Drosophila melanogaster7227EukaryoteFruit fly6Caenorhabditis elegans6239EukaryoteRoundworm2Bacteria2ProkaryoteBacteria19Schizosaccharomyces pombe4896Eukaryote21Xenopus laevis8355EukaryoteAfrican clawed frog25Escherichia coli (strain K12)83333Prokaryote49Bathymodiolus platifrons220390EukaryoteDeep sea mussel60Nitzschia sp.0001EukaryoteNitzschia429Saccharomyces cerevisiae (strain ATCC 204508 / S288c)559292EukaryoteBaker's yeast15Plasmodium falciparum5833Eukaryote301Gallus Gallus1758Prokaryote5CytoplasmGO:00057371CytosolGO:000582935ChloroplastGO:00095073Mitochondrial MatrixGO:000575914Mitochondrial Outer MembraneGO:00057412MitochondrionGO:000573915NucleusGO:00056344PeroxisomeGO:000577713Endoplasmic ReticulumGO:00057837Endoplasmic Reticulum MembraneGO:000578910Cell MembraneGO:000588627Peroxisome MembraneGO:000577831Periplasmic SpaceGO:000562011Extracellular SpaceGO:000561512Mitochondrial Inner MembraneGO:000574332Inner MembraneGO:007025819Sarcoplasmic ReticulumGO:001652936MembraneGO:00160206LysosomeGO:000576424Mitochondrial Intermembrane SpaceGO:000575825Golgi ApparatusGO:000579416Lysosomal LumenGO:004320218Melanosome MembraneGO:003316220Endoplasmic Reticulum LumenGO:000578821SynapseGO:004520253Endoplasmic Reticulum BodyGO:001016834Plant-Type VacuoleGO:000032540PeriplasmGO:00425978Smooth Endoplasmic Reticulum GO:000579039Mitochondrial membraneGO:00319662Endothelium BTO:00003931LiverBTO:00007597297Nervous SystemBTO:000148418PancreasBTO:000098825IntestineBTO:00006488Blood VesselBTO:000110274115cardiocyteBTO:00015394Adrenal 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1011PW_BS0005806443-Phosphoglyceric acidHMDB00008073-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia).820-11-1C0059772417050G3P704OC(COP(O)(O)=O)C(O)=OC3H7O7PInChI=1S/C3H7O7P/c4-2(3(5)6)1-10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)OSJPPGNTCRNQQC-UHFFFAOYSA-N186.0572185.99293909FDB0222553-(dihydrogen phosphate)glycerate;3-(dihydrogen phosphate)glyceric acid;3-glycerophosphorate;3-glycerophosphoric acid;3-p-d-glycerate;3-p-glycerate;3-pga;3-pg;3-phospho-(r)-glycerate;3-phospho-d-glycerate;3-phospho-glycerate;3-phospho-glyceric acid;3-phosphoglycerate;3-phosphoglyceric acid;D-(-)-3-phosphoglyceric acid;D-glycerate 3-phosphate;G3p;Glycerate 3-phosphate;Glycerate-3-p;Glyceric acid 3-phosphate;Phosphoglycerate;Dl-glycerate 3-phosphate;Glycerate 3-phosphates;3-(dihydrogen phosphoric acid)glyceric acid;2-hydroxy-3-phosphonooxypropanoate;Dl-glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphoric acid;Glyceric acid 3-phosphatesPW_C000644G3P205182257257431175917147594815168971608358225426233227711113278033111121192124121386122123763118123945135125960299127417388414Adenosine 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-N507.181506.995745159FDB0218135'-(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_C000414ATP9221460826616414224781373332799593439976321051821121021464921561421605824055924342727264628122930296631637236166136175143992344743147689148645450328950352651557520597521510052501045291101531311153461125390103540611754301185443120554212955561325569133560313556211085846143585414658761075897147592415160481556109161623016664931786839188687016069761997157205718420672092107225213722921172981987302216739021774082187432163748122274991908186225118472771190317012010281120391641217828512578226126912901326422315327308423263154262132242694318770282537721813477233329774683337763233678037332780413507816812878214351782403537841133578494115788501307886533178919334800283688004618480674119856291948261241132349411328238811628010911991412211999240612015440712024538212036241212124642912139212312139743312147140812197441012206512512207938312208340512240242212244443512291939912300944612381646412395144712395646812402937412452744412461613612463039812463437612494347212497237512501147012530429712537147912539229912551548112559548412612348512622030012623449512624047812654749112659649912691350112712338912773151612778139512779639012780120912811950812816751714077089190Glyceric acidHMDB0000139Glyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.473-81-4C00258439194323982-PG388334OC[C@@H](O)C(O)=OC3H6O4InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1RBNPOMFGQQGHHO-UWTATZPHSA-N106.0773106.02660868FDB012242(r)-glycerate;D-glycerate;D-glyceric acid;Glycerate;Glyceric acid;A,b-hydroxypropionate;A,b-hydroxypropionic acid;Alpha,beta-hydroxypropionic acid;R-glyceric acid;Alpha,beta-hydroxypropionate;α,β-hydroxypropionate;α,β-hydroxypropionic acid;R-glyceratePW_C000090Glycera2052834762573910860141474262031578034111781071321213871221221551241239461351247071181263132991278743881034Adenosine 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-N427.2011427.029414749FDB021817Adp;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_C001034ADP234134841522482138015963159783106114151821901492104182113102161582408592435272728472736462855293165723635614400234476314770915036265157752089752171005315111534911253921035446120554412955721335624108574111757641015849143585614658781075899147592615160501556111161623116664951786700946841188687216071592057187206720821072262137231211730019873032167391217741021874331637483222818722511851277119051701201328112180285132622231532930842328315423983134262232242696318770292537708713277216134773063297747233377663336780393327804335078170128782153517824435378414335784951157870533178849130789203348003036880622118806511358067611994827124113283388116204109119944122119994406120156407120318382120366412121248429121394123121399433121472408121899383121976410122064125122085405122405422122445435122973399123013446123818464123953447123958468124030374124452398124529444124615136124636376124947472124975375125012470125334297125373479125492299125517481125645484126125485126219300126235495126242478126550491126597499126915501127733516127780395127797390127803209128122508128168517128313389828GlyceraldehydeHMDB0001051Glyceraldehyde is a triose monosaccharide with chemical formula C3H6O3. It is the simplest of all common aldoses. It is a sweet, colourless crystalline solid that is an intermediate compound in carbohydrate metabolism. The word "glyceraldehyde" comes from combining glycerine and aldehyde, as glyceraldehyde is merely glycerine with one hydroxide changed to an aldehyde. Glyceraldehyde is produced from the action of the enzyme glyceraldehyde dehydrogenase, which converts glycerol to glyceraldehyde using NADP as a cofactor. When present at sufficiently high levels, glyceraldehyde can be a cytotoxin and a mutagen. A cytotoxin is a compound that kills cells. A mutagen is a compound that causes mutations in DNA. Glyceraldehyde is a highly reactive compound that can modify and cross-link proteins. Glyceraldehyde-modified proteins appear to be cytotoxic, depress intracellular glutathione levels, and induce reactive oxygen species (ROS) production (PMID: 14981296). Glyceraldehyde has been shown to cause chromosome damage to human cells in culture and is mutagenic in the Ames bacterial test.56-82-6C021547515445GLYCERALD731OCC(O)C=OC3H6O3InChI=1S/C3H6O3/c4-1-3(6)2-5/h1,3,5-6H,2H2MNQZXJOMYWMBOU-UHFFFAOYSA-N90.077990.031694058FDB022392(+/-)-2,3-dihydroxy-propanal;(+/-)-glyceraldehyde;2,3-dihydroxypropanal;2,3-dihydroxypropionaldehyde;D-(+)-glyceraldehyde;D-2,3-dihydroxypropanal;D-2,3-dihydroxypropionaldehyde;D-aldotriose;D-glyceraldehyde;D-glycerose;Dl-glyceraldehyde;Dihydroxypropionaldehyde;Glyceraldehyde;Glyceric aldehyde;Glycerinaldehyde;Glycerinformal;Glycerose;Alpha,beta-dihydroxypropionaldehyde;Delta-(+)-glyceraldehyde;Delta-2,3-dihydroxypropanal;Delta-2,3-dihydroxypropionaldehyde;Delta-aldotriose;Delta-glyceraldehyde;Delta-glycerose;(+-)-glyceraldehyde;Aldotriose;Gliceraldehido;Glyceraldehyd;Glycerinaldehyd;GlyzerinaldehydPW_C000828Glycald103881336415177947111120751122123348135143NADPHMDB0000217Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5-phosphate (NMN) coupled by pyrophosphate linkage to the 5-phosphate adenosine 2,5-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds).53-59-8C00006588618009NAD(P)5675NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H28N7O17P3InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1XJLXINKUBYWONI-NNYOXOHSSA-N743.405743.075452041FDB021908Adenine-nicotinamide dinucleotide phosphate;Codehydrase ii;Codehydrogenase ii;Coenzyme ii;Cozymase ii;Nad phosphate;Nadp;Nadp+;Nicotinamide adenine dinucleotide phosphate;Nicotinamide-adenine dinucleotide phosphate;Tpn;Triphosphopyridine nucleotide;B-nadp;B-nicotinamide adenine dinucleotide phosphate;B-tpn;Beta-nadp;Beta-nicotinamide adenine dinucleotide phosphate;Beta-tpn;Oxidized nicotinamide-adenine dinucleotide phosphate;B-nicotinamide adenine dinucleotide phosphoric acid;Beta-nicotinamide adenine dinucleotide phosphoric acid;β-nicotinamide adenine dinucleotide phosphate;β-nicotinamide adenine dinucleotide phosphoric acidPW_C000143NADP183819137685780108241883921611291617494685314796144801145308111579010860171476132159627335677811770691887105163715220572061607317213734621075622127589170819722582201518419224118111981189721112008222121521641224928612597226126502494234431543745322769132937716413277384331773963327746113077515115776243367781433477870112807131191131659412010640712042940512045012212060440812061812312114212512127742912140112412148538312306337612308413512322937412324344712371313612384846412396011812404339812547348112569429712574348212621529912652849512701020612722550212757038812810039014070916885GlycerolHMDB0000131Glycerol 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-N92.093892.047344122FDB0007561,2,3-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_C000085Ifp2063822161530939629710862981079232170125451514244831842449315779031137803511178064114121229126121389122121435409123799443123948135123993137146NADPHHMDB0000221Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.).53-57-6C000052283351216474NADPH17215925NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](OP(O)(O)=O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H30N7O17P3InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1ACFIXJIJDZMPPO-NNYOXOHSSA-N745.4209745.091102105FDB0219092'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-d-ribofuranosylnicotinamide;2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-d-ribofuranosyl-3-pyridinecarboxamide;Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide;Dihydrocodehydrogenase ii;Dihydronicotinamide adenine dinucleotide phosphate;Dihydronicotinamide adenine dinucleotide-p;Dihydrotriphosphopyridine nucleotide reduced;Nadp-reduced;Nadph;Nicotinamide-adenine-dinucleotide-phosphorate;Nicotinamide-adenine-dinucleotide-phosphoric acid;Reduced codehydrase ii;Reduced coenzyme ii;Reduced cozymase ii;Reduced triphosphopyridine nucleotide;Triphosphopyridine nucleotide reduced;B-nadph;B-nicotinamide-adenine-dinucleotide-phosphorate;B-nicotinamide-adenine-dinucleotide-phosphoric acid;Beta-nadph;Beta-nicotinamide-adenine-dinucleotide-phosphorate;Beta-nicotinamide-adenine-dinucleotide-phosphoric acid;Nicotinamide adenine dinucleotide phosphate - reducedPW_C000146NADPH1858190377810796582118837216092916154946873147931447971453101115789108597214761281596271356779117706818871031637154205720516073152137345210755921275911708194225821915184212241181219811893211120062221215016412245286125962261264824942343315437463227691129377166132773853317739433277460130775041127751111577623336807121191131649412010540712042540512045212212061612312114112512127542912140212412148338312305937612308613512324144712371213612384646412396111812404139812547248112569629712621429912652949512700920612757238812810139014070616881Glycerol 3-phosphateHMDB0000126Glycerol 3-phosphate is a chemical intermediate in the glycolysis metabolic pathway. It is commonly confused with the similarly named glycerate 3-phosphate or glyceraldehyde 3-phosphate. Glycerol 3-phosphate is produced from glycerol, the triose sugar backbone of triglycerides and glycerophospholipids, by the enzyme glycerol kinase. Glycerol 3-phospate may then be converted by dehydrogenation to dihydroxyacetone phosphate (DHAP) by the enzyme glycerol-3-phosphate dehydrogenase. DHAP can then be rearranged into glyceraldehyde 3-phosphate (GA3P) by triose phosphate isomerase (TIM), and feed into glycolysis. The glycerol 3-phosphate shuttle is used to rapidly regenerate NAD+ in the brain and skeletal muscle cells of mammals (wikipedia).17989-41-2C0009343916215978GLYCEROL-3P388308DB02515OC[C@@H](O)COP(O)(O)=OC3H9O6PInChI=1S/C3H9O6P/c4-1-3(5)2-9-10(6,7)8/h3-5H,1-2H2,(H2,6,7,8)/t3-/m1/s1AWUCVROLDVIAJX-GSVOUGTGSA-N172.0737172.013674532FDB0218001-(dihydrogen phosphate) glycerol;1-glycerophosphate;1-glycerophosphorate;1-glycerophosphoric acid;3-glycerophosphate;Dl-glycerol 1-phosphate;Dl-glycerol 3-phosphate;Dl-a-glycerol phosphate;Dl-a-glycerophosphate;Dl-a-glycerophosphorate;Dl-a-glycerophosphoric acid;Dl-a-glyceryl phosphate;Dl-alpha-glycerol phosphate;Dl-alpha-glycerophosphate;Dl-alpha-glycerophosphorate;Dl-alpha-glycerophosphoric acid;Dl-alpha-glyceryl phosphate;Dihydrogen a-glycerophosphate;Glycerol 1-phosphate;Glycerol a-phosphate;Glycerol monophosphate;Glycerophosphate;Glycerophosphorate;Glycerophosphoric acid;Glycerophosphoric acid i;Glyceryl phosphate;Sn-gro-1-p;Sn-glycerol 3-phosphate;A-glycerophosphate;A-glycerophosphorate;A-glycerophosphoric acid;A-phosphoglycerol;Alpha-glycerophosphate;Alpha-glycerophosphorate;Alpha-glycerophosphoric acid;Alpha-phosphoglycerol;D-glycerol 1-phosphate;Glycerol 3-phosphoric acid;D-glycerol 1-phosphoric acidPW_C000081Glyc1P1043814752148842211558629510762961088412162912217010653188125461511255022315319249348141742466318424673157803011178052350783723457837813279952134818082539382612494789384110553388110636391115840118120756122121297418121345121121415433123353135123867454123974468125788297125978489125991299127243205127431506721NADHMDB0000902NAD (or Nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be converted to ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it by cellular respiration. (wikipedia). Nicotinamide adenine dinucleotide is a A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). (Dorland, 27th ed).53-84-9C00003589315846NAD5682NC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1OC21H27N7O14P2InChI=1S/C21H27N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BAWFJGJZGIEFAR-NNYOXOHSSA-N663.4251663.109121631FDB0223093-carbamoyl-1-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;3-carbamoyl-1-beta-d-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-beta-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate inner salt;3-carbamoyl-1-delta-ribofuranosylpyridinium hydroxide 5'-ester with adenosine 5'-pyrophosphate;Adenine-nicotinamide dinucleotide;Co-i;Codehydrase i;Codehydrogenase i;Coenzyme i;Cozymase;Cozymase i;Diphosphopyridine nucleotide;Diphosphopyridine nucleotide oxidized;Endopride;Nad trihydrate;Nad-oxidized;Nicotinamide adenine dinucleotide;Nicotinamide adenine dinucleotide oxidized;Nicotinamide dinucleotide;Nicotineamide adenine dinucleotide;Oxidized diphosphopyridine nucleotide;Pyridine nucleotide diphosphate;[(3s,2r,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(3s,2r,4r,5r)-5-(3-carbamoylpyridyl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxyphosphoryl) hydrogen phosphate;[adenylate-32-p]-nad;Beta-diphosphopyridine nucleotide;Beta-nad;Beta-nicotinamide adenine dinucleotide;Beta-nicotinamide adenine dinucleotide trihydrate;Dpn;Nad;Nad+;Nadide;B-nad;β-nadPW_C000721NAD140415033538651101114211344312735146654222949277917283529310794807184813184819284902649603151679552381035334111536011254691235482125559013556101185696100573810858271415912147594215160241556072157607616163851646917867721176890160701218870971637174205719720674051987459222824122683592259085224118192161232224913006298130183001325622342404322426193157710413277120133772091347737033177650336776673347770233277709130779151137798334778406356800063688069011993825124110552388112750166112853941199291221199524061201714071208344191209844081211594251212421261212594291218173831226143841227421201231304471231411361234194551235493741237314601238124431238294641243703981251871211253192971253424791255304811258062991258254901259244821265154951267654801268855011272785071273835021280893901283603911284283951407571851134Dihydroxyacetone phosphateHMDB0001473Dihydroxyacetone phosphate, also known as 3-phosphate, dihydroxyacetone or 3-hydroxy-2-oxopropyl phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Dihydroxyacetone phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). Dihydroxyacetone phosphate has been detected in multiple biofluids, such as saliva and blood. Within the cell, dihydroxyacetone phosphate is primarily located in the peroxisome, mitochondria and cytoplasm. Dihydroxyacetone phosphate exists in all living organisms, ranging from bacteria to humans. In humans, dihydroxyacetone phosphate is involved in cardiolipin biosynthesis CL(i-13:0/i-21:0/a-17:0/i-14:0) pathway, cardiolipin biosynthesis CL(i-14:0/a-13:0/i-19:0/a-25:0) pathway, cardiolipin biosynthesis CL(i-12:0/i-13:0/i-17:0/i-12:0) pathway, and cardiolipin biosynthesis CL(a-13:0/18:2(9Z,11Z)/i-20:0/i-22:0) pathway. Dihydroxyacetone phosphate is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(8:0/a-21:0/13:0) pathway, de novo triacylglycerol biosynthesis TG(16:0/20:5(5Z,8Z,11Z,14Z,17Z)/20:3(5Z,8Z,11Z)) pathway, de novo triacylglycerol biosynthesis TG(i-20:0/i-21:0/19:0) pathway, and de novo triacylglycerol biosynthesis TG(i-22:0/17:0/i-14:0) pathway. Outside of the human body, dihydroxyacetone phosphate can be found in a number of food items such as towel gourd, boysenberry, jujube, and prunus (cherry, plum). This makes dihydroxyacetone phosphate a potential biomarker for the consumption of these food products. Dihydroxyacetone phosphate is an important intermediate in lipid biosynthesis and in glycolysis.57-04-5C0011166816108DIHYDROXY-ACETONE-PHOSPHATE648DB04326OCC(=O)COP(O)(O)=OC3H7O6PInChI=1S/C3H7O6P/c4-1-3(5)2-9-10(6,7)8/h4H,1-2H2,(H2,6,7,8)GNGACRATGGDKBX-UHFFFAOYSA-N170.0578169.998024468FDB0016181,3-dihydroxy-2-propanone mono(dihydrogen phosphate);1,3-dihydroxy-2-propanone phosphate;1,3-dihydroxyacetone 1-phosphate;1-hydroxy-3-(phosphonooxy)-2-propanone;1-hydroxy-3-(phosphonooxy)acetone;Dhap;Di-oh-acetone-p;Dihydroxy-acetone-p;Dihydroxy-acetone-phosphate;Dihydroxyacetone 3-phosphate;Dihydroxyacetone monophosphate;Dihydroxyacetone phosphate;Dihydroxyacetone-p;Dihydroxyacetone-phosphate;Glycerone phosphate;Glycerone-phosphate;Phosphoric acid ester with 1,3-dihydroxy-2-propanone;1,3-dihydroxy-2-propanone monodihydrogen phosphate;3-hydroxy-2-oxopropyl phosphate;Glycerone monophosphate;1,3-dihydroxy-2-propanone monodihydrogen phosphoric acid;Glycerone phosphoric acid;1,3-dihydroxy-2-propanone phosphoric acid;1,3-dihydroxyacetone 1-phosphoric acid;3-hydroxy-2-oxopropyl phosphoric acid;Dihydroxyacetone monophosphoric acid;Dihydroxyacetone phosphoric acid;Glycerone monophosphoric acidPW_C001134Dhapp10268147423305542534258131085908147593615168841604266031577098132779341117837434578559334938241241105513881158391181207331221225644181225904081233331351251374541251623741257872971259502991267124891267364821272422051283035061283305021144NADHHMDB0001487NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH, A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). It forms NADP with the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage.(Dorland, 27th ed).58-68-4C0000443915316908NADH388299DB00157NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1OC21H29N7O14P2InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1BOPGDPNILDQYTO-NNYOXOHSSA-N665.441665.124771695FDB0226491,4-dihydronicotinamide adenine dinucleotide;Dpnh;Dihydrocodehydrogenase i;Dihydrocozymase;Dihydronicotinamide adenine dinucleotide;Dihydronicotinamide mononucleotide;Enada;Nadh;Nadh2;Reduced codehydrogenase i;Reduced diphosphopyridine nucleotide;Reduced nicotinamide adenine diphosphate;Reduced nicotinamide-adenine dinucleotide;B-dpnh;B-nadh;Beta-dpnh;Beta-nadh;Nicotinamide adenine dinucleotide (reduced);Reduced nicotinamide adenine dinucleotidePW_C001144NADH143415334908648101115212755146954223049278117283629310994806184812184821284904649593151699552401035332111535811254661235479125559313556981005737108582914159151475945151602715560791616387164721786771117689316070111887099163717220571952067462222824422683602259086224118091981182121612320249130032981301530013255223424033224261831577107132771231337720813477371331776513367766833477700332777071307791711377986347800093688069111993822124110549388112854941158381181199554061201724071203781221209864081211624251212441261216934291218183831226163841227451201231274471231381361235513741237344601238144431242424641243713981251891211253454791255314811257622971258082991259264821265164951267674801268885011273855021280903901283623911284293951407591853904LysoPA(16:0/0:0)HMDB0007853LPA(16:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.C00681641970115799ACYL-SN-GLYCEROL-3P4925335CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=OC19H39O7PInChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)YNDYKPRNFWPPFU-UHFFFAOYSA-N410.4825410.243340114FDB0250461-hexadecanoyl-phosphatidic acid;1-palmitoyl lysophosphatidate;1-palmitoyl lysophosphatidic acid;1-palmitoyl-glycero-3-phosphate;1-palmitoylglycerol 3-phosphate;1-palmitoyllysophosphatidate;1-palmitoyllysophosphatidic acid;2-hydroxy-3-(phosphonooxy)propyl ester hexadecanoate;2-hydroxy-3-(phosphonooxy)propyl ester hexadecanoic acid;Lpa(16:0);Lpa(16:0/0:0);Lysopa(16:0/0:0);Lysophosphatidic acid(16:0);Lysophosphatidic acid(16:0/0:0);(2r)-2-hydroxy-3-(phosphonooxy)propyl palmitate;1-hexadecanoyl-sn-glycero-3-phosphate;(2r)-2-hydroxy-3-(phosphonooxy)propyl palmitic acidPW_C003904LPA16:0147749149342208610213458912517015323249254922278046332780553507851933178527345818113299385438293855383108547288110593389110594390115920399115921398121302418121405123121419433123872454123964447123978468125969495125983489127436506531PA(16:0/16:0)HMDB0000674PA(16:0/16:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(16:0/16:0), in particular, consists of two hexadecanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.7091-44-3C0041644606673246L-PHOSPHATIDATE393518[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCC35H69O8PInChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1PORPENFLTBBHSG-MGBGTMOVSA-N648.903648.47300618FDB0221751,2-di-o-palmitoyl-3-sn-glyceryl-o-phosphorate;1,2-di-o-palmitoyl-3-sn-glyceryl-o-phosphoric acid;1,2-dihexadecanoyl-rac-phosphatidic acid;1,2-dipalmitoyl-3-sn-phosphatidate;1,2-dipalmitoyl-3-sn-phosphatidic acid;1,2-dipalmitoyl-sn-glycerol 3-phosphate;1,2-dipalmitoyl-sn-glycerol-3-phosphorate;1,2-dipalmitoyl-sn-glycerol-3-phosphoric acid;Dipalmitoyl-l-a-phosphatidate;Dipalmitoyl-l-a-phosphatidic acid;Dipalmitoyl-l-alpha-phosphatidate;Dipalmitoyl-l-alpha-phosphatidic acid;Dipalmitoylphosphatidate;Dipalmitoylphosphatidic acid;L-a-dipalmitoyl-phosphatidate;L-a-dipalmitoyl-phosphatidic acid;L-a-dipalmitoylphosphatidate;L-a-dipalmitoylphosphatidic acid;L-alpha-dipalmitoyl-phosphatidate;L-alpha-dipalmitoyl-phosphatidic acid;L-alpha-dipalmitoylphosphatidate;L-alpha-dipalmitoylphosphatidic acid;Pa(32:0);Phosphatidic acid(16:0/16:0);Phosphatidic acid(32:0);1,2-dipalmitoyl-sn-glycerol-3-phosphate;Dipalmitoyl phosphatidic acid;Pa(16:0/16:0)PW_C000531PA32:01480491494421535142107102140586912197691318991301889138195152981511532524936244223624617780383327804235078520331785283457853711585376329853771349385738394782382947853841085492881085502231105963901106983891106993911159233981213034181213214051213931231213984331216623991216641211238734541238913761239524471239574681259704951259844891260024781274375061274532093149DG(16:0/16:0)HMDB0007098DG(16:0/16:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(16:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.30334-71-5C00165644078237189DIACYLGLYCEROL559127[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC35H68O5InChI=1S/C35H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36H,3-32H2,1-2H3/t33-/m0/s1JEJLGIQLPYYGEE-XIFFEERXSA-N568.9114568.506675286FDB0242921,2-dipalmitoyl-rac-glycerol;Dag(16:0/16:0);Dag(32:0);Dg(16:0/16:0);Dg(32:0);Diacylglycerol;Diacylglycerol(16:0/16:0);Diacylglycerol(32:0);Diglyceride;(s)-1-(hydroxymethyl)ethane-1,2-diyl dipalmitate;1,2-dihexadecanoyl-sn-glycerol;Dg(16:0/16:0/0:0);(s)-1-(hydroxymethyl)ethane-1,2-diyl dipalmitic acidPW_C003149DG32:0152543210910214358218415913616092241709259195127811511529928515385497803633278040350780591147853535681813331938583831105973901156723981213184191213911231213964331214264091238884551239504471239554681239841371259994901274505071031Palmitoyl-CoAHMDB0001338Palmitoyl-CoA, also known as palmityl CoA or CoA, palmitoyl, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Palmityl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Palmityl-CoA has been found throughout most human tissues, and has also been primarily detected in urine. Within the cell, palmityl-CoA is primarily located in the cytoplasm and mitochondria. In humans, palmityl-CoA is involved in cardiolipin biosynthesis CL(16:0/18:2(9Z,12Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) pathway, cardiolipin biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, cardiolipin biosynthesis CL(16:0/18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)) pathway, and cardiolipin biosynthesis CL(22:5(7Z,10Z,13Z,16Z,19Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:1(9Z)) pathway. Palmityl-CoA is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/16:0/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(16:0/14:1(9Z)/14:1(9Z)) pathway, de novo triacylglycerol biosynthesis TG(a-25:0/i-14:0/16:0) pathway, and de novo triacylglycerol biosynthesis TG(20:3(5Z,8Z,11Z)/16:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway. Palmityl-CoA is a fatty acid coenzyme derivative which plays a key role in fatty acid oxidation and biosynthesis.1763-10-6C001541566715525PALMITYL-COA14902CCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2NC37H66N7O17P3SInChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/t26-,30-,31-,32+,36-/m1/s1MNBKLUUYKPBKDU-BBECNAHFSA-N1005.9431005.344873947FDB022562Hexadecanoyl coa;Hexadecanoyl coenzyme a;Palmitoyl coa;Palmitoyl coenzyme a;Palmitoyl-coa;Palmitoyl-coenzyme a;Palmityl-coa;Palmityl-coenzyme a;S-hexadecanoate;S-hexadecanoate coa;S-hexadecanoate coenzyme a;S-hexadecanoic acid;S-palmitoylcoenzyme a;CoA(16:0)PW_C001031COA16:08753880228901716471420901020962522910252441046958162697019971291637201160912317091291889214195255034977219134772273297789311278045332780491327854911579257333818443319076721095706383971203821085972881111033891142053901202283841206644071213564051214041231214111241229011211229143991232781191239153761239634471239701181255764801255894841260264811260284781262082991271063911274782061274802091277703881288473981407481861407648912417TG(16:0/16:0/16:0)HMDB0005356TG(16:0/16:0/16:0) or Tripalmitin is a monoacid triglyceride. Triglycerides (TGs) are also known as triacylglycerols or triacylglycerides. TGs are fatty acid triesters of glycerol and 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. 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)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.555-44-2111477739310674[H]C(COC(=O)CCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCC51H98O6InChI=1S/C51H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-49(52)55-46-48(57-51(54)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)47-56-50(53)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h48H,4-47H2,1-3H3PVNIQBQSYATKKL-UHFFFAOYSA-N807.3202806.736340868FDB0029111,2,3-trihexadecanoyl-sn-glycerol;Barolub lcd;Dynasan 116;Dynosan 114;Glycerin tripalmitate;Glycerol tripalmitate;Glyceryl trihexadecanoate;Glyceryl trihexadecanoic acid;Glyceryl tripalmitate;Palmitic triglyceride;Spezialfett 116;Triglyceride ppp;Triglyceryl palmitate;Tripalmitate;Tripalmitin;Tripalmitoylglycerol;1,2,3-propanetriol trihexadecanoate;1,2,3-propanetriyl trihexadecanoate;1,2,3-trihexadecanoylglycerol;Hexadecanoic acid, 1,2,3-propanetriyl ester;Palmitic acid triglycerin ester;Tg 16:0/16:0/16:0;Tg(16:0/16:0/16:0);Trihexadecanoylglycerol;1,2,3-propanetriol trihexadecanoic acid;2,3-di(hexadecanoyloxy)propyl hexadecanoic acid;1,2,3-propanetriyl trihexadecanoic acid;Glycerin tripalmitic acid;Glycerol tripalmitic acid;Glyceryl tripalmitic acid;Hexadecanoate, 1,2,3-propanetriyl ester;Palmitate triglycerin ester;Triglyceryl palmitic acidPW_C002417TG162111102176144620213378151254954978050132780581158181533193860383110599390115925398121412124121425405123971118123983376145Palmitic acidHMDB0000220Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent.57-10-3C0024998515756CPD-8475960DB03796CCCCCCCCCCCCCCCC(O)=OC16H32O2InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)IPCSVZSSVZVIGE-UHFFFAOYSA-N256.4241256.240230268FDB0116791-hexyldecanoate;1-hexyldecanoic acid;1-pentadecanecarboxylic acid;C16 fatty acid;Cetylic acid;Edenor c16;Emersol 140;Emersol 143;Glycon p-45;Hexadecanoate;Hexadecanoic acid;Hexadecanoic acid palmitic acid;Hexadecoate;Hexadecoic acid;Hexadecylic acid;Hexaectylic acid;Hydrofol;Hydrofol acid 1690;Hystrene 8016;Hystrene 9016;Industrene 4516;Kortacid 1698;Loxiol ep 278;Lunac p 95;Lunac p 95kc;Lunac p 98;N-hexadecanoate;N-hexadecanoic acid;N-hexadecoate;N-hexadecoic acid;Pam;Plm;Palmitate;Palmitic acid;Palmitinate;Palmitinic acid;Palmitinsaeure;Palmitoate;Palmitoic acid;Pentadecanecarboxylate;Pentadecanecarboxylic acid;Prifac 2960;Prifrac 2960;Pristerene 4934;Univol u332;C16:0;Ch3-[ch2]14-cooh;1-pentadecanecarboxylate;Cetylate;Hexadecylate;Hexaectylate;Hexadecanoate (n-c16:0);FA(16:0)PW_C00014516:0876387822217714218122185152843292898852491046447105644810765151086957160697519971301638311210922317012916151129182264252332042524318425253157723232977655336778611327789411278060115780611141202443821206654071214274051214294091214311241216994291229183991232791191239853761239871371239891181242494641255944841266372991271223891282133881407698917130MG(0:0/16:0/0:0)HMDB0011533MG-2(0:0/16:0/0:0) belongs to the family of monoradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at one fatty acyl group is attached. Their general formula is [R1]OCC(CO[R2])O[R3]. MG-2(0:0/16:0/0:0) is made up of one hexadecanoyl(R2).12340975455110006[H]C(CO)(CO)OC(=O)CCCCCCCCCCCCCCCC19H38O4InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-18(16-20)17-21/h18,20-21H,2-17H2,1H3BBNYCLAREVXOSG-UHFFFAOYSA-N330.5026330.2770097041-monoacylglyceride;1-monoacylglycerol;2-hexadecanoyl-rac-glycerol;2-palmitoyl-glycerol;Mag(0:0/16:0);Mag(16:0);Mg(0:0/16:0);Mg(16:0);B-monoacylglycerol;Beta-monoacylglycerol;1,3-dihydroxypropan-2-yl palmitate;2-hexadecanoylglycerol;2-monopalmitin;2-monopalmitoylglycerol;2-o-palmitoylglycerol;Mg (0:0/16:0/0:0);1,3-dihydroxypropan-2-yl palmitic acidPW_C007130MG016022141512784151780631141214334091239911371420WaterHMDB0002111Water 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-N18.015318.010564686FDB013390Dihydrogen oxide;Steam;[oh2];Acqua;Agua;Aqua;Bound water;Dihydridooxygen;Eau;H2o;Hoh;Hydrogen hydroxide;WasserPW_C001420H2O55894910951394151316214481135261562428652106912077033823188382109431137749146554159043201824253222267860272746277817280529314370316472363461459836472737494193503027515675195975214100522794523610352971055319111534311353551125402110547012354831255492126550712755341305537114554112955911355608118562210856916575914057781015841143585314658771075890955910147594015160321556059157608716161231636133159621516218166647717865071806600152671311768401886888160716220571812077193206721121172282137238214724321572951987350216738821074012127467222749222475001907588170820122582372268414162926526118502771192216412011281122132851225028612264287123272491252022712632651269329012705291127152921300729813019300130253011303730213261223133272941534030842327315426953184369132276914293770192537710213277131133772151347737833177397332774713337751611577536334776283367772233777759341778163437798234778071329782353527824235378270356791133608001436880039370805912288065611993830383947943841105573901106393911158443981198792321199151221199634061200084071200464081201131241203654121204304051204384091206064151207944141211584251212404291213511211213814191216074341221183821223844361227531201227973741228044431230124461230643761230721371231314471231421361231624481232314511233844501237304601238104641239404551241654691246703991249384711249454721253052971253534791253864811254244821254802991256824831257074781257454871260544901262384951262734841267644801268965011269635021270173881271772081271992091272275041275065071275765151278363891280823951281765131406747901406758341407551851099Coenzyme 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-N767.534767.115208365FDB022614Acetoacetyl 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_C001099CoA21143868845387922892172407592414224595281329286231334211335118461810462958484214486554487965232102524710452801035477124573410857771016023155607516163841646817869301606961162697319970831887108163729319873472107458222822915190812269090224912417092151951301329915318249254884942616315769072937711913377222134772303297729211177550132775553347756311277633336776721297799611578047332780563507841333578567130792593337997433180005368806201188062737480635119806653769382838293834383986742881105553891105613901158423991158473981199514061201474051202313841203051221206344071207621171214061231214214331215211251216664291216824081217144141224044221227411201229041211229601351239654471239794681240791361242204641242654501249743751253414791255094781255794801255924841256342971260844811265494911265604821267463001268845011270462091271093911273012051275402061276673881281215081281335021283403951407511861407631851407678911104PhosphateHMDB0001429Phosphate 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-85871032OP(O)(O)=OH3O4PInChI=1S/H3O4P/c1-5(2,3)4/h(H3,1,2,3,4)NBIIXXVUZAFLBC-UHFFFAOYSA-N97.995297.976895096DBMET00532FDB022617Nfb 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_C001104Pi24484881458181883129803176314176749250010272947273746312929316672363661385123424922447531503127515875207975216100531711153511125381103544712055431295573133560513556251085693658481435855146591114759411516040155610016162941076487178669110167141176842188688916071612057189206721221173061987389210740221274361637475222819622582582271011824110134257117481321176111511773213119041701192716412014281127282901326322334819174225530442350315424353184369232277018253771942937721713477940336779661307804833278057329782453537866933180022368892793089383138394796384110558390110640391113235941158453981162061091199824061200691221206994071210571241212161251212684291213521211214091231214233821218524051233041191236211181237861361238384641239684471239813991244053761249484721253624791254462971257744811259542991262214781265943001266042981267234841269045011274133881277832091281663951281775131283153891860QuinoneHMDB0003364Quinone is also called 1,4-benzoquinone or cyclohexadienedione. Quinones are oxidized derivatives of aromatic compounds and are often readily made from reactive aromatic compounds with electron-donating substituents such as phenols and catechols, which increase the nucleophilicity of the ring and contributes to the large redox potential needed to break aromaticity. Derivatives of quinones are common constituents of biologically relevant molecules. Some serve as electron acceptors in electron transport chains such as those in photosynthesis (plastoquinone, phylloquinone), and aerobic respiration (ubiquinone). Quinone is a common constituent of biologically relevant molecules (e.g. Vitamin K1 is phylloquinone). A natural example of quinones as oxidizing agents is the spray of bombardier beetles. Hydroquinone is reacted with hydrogen peroxide to produce a fiery blast of steam, a strong deterent in the animal world.106-51-4C00472465016509CPD-81304489O=C1C=CC(=O)C=C1C6H4O2InChI=1S/C6H4O2/c7-5-1-2-6(8)4-3-5/h1-4HAZQWKYJCGOJGHM-UHFFFAOYSA-N108.0948108.021129372FDB0057551,4-benzoquine;1,4-benzoquinone;1,4-cyclohexadiene dioxide;1,4-cyclohexadienedione;1,4-diossibenzene;1,4-dioxy-benzol;1,4-dioxybenzene;2,5-cyclohexadiene-1,4-dione;2,5-cyclohexadiene-1-4-dione;Benzo-1,4-quinone;Benzo-chinon;Benzoquinone;Benzoquinone [un2587];Chinon;Chinone;Cyclohexadiene-1,4-dione;Cyclohexadienedione;Eldoquin;Para-benzoquinone;Para-quinone;Quinone1,4-benzoquinone;Semiquinone anion;Semiquinone radicals;P-benzoquinone;P-chinon;P-quinone;1,4-benzochinon;QuinonePW_C001860Quinone1184332707238351446222249003589195780311127805132978728132788063431207584071208844151214143821222031241233551191234604511239733991247551181257904811263652991272452061273065041279283881632HydroquinoneHMDB0002434Hydroquinone, also known as benzene-1,4-diol, is an aromatic organic compound which is a type of phenol, having the chemical formula C6H4(OH)2. Its chemical structure has two hydroxyl groups bonded to a benzene ring in a para position. Hydroquinone is commonly used as a biomarker for benzene exposure. The presence of hydroquinone in normal individuals stems mainly from direct dietary ingestion, catabolism of tyrosine and other substrates by gut bacteria, ingestion of arbutin-containing foods, cigarette smoking, and the use of some over-the-counter medicines. Hydroquinone is a white granular solid at room temperature and pressure. The hydroxyl groups of hydroquinone are quite weakly acidic. Hydroquinone can lose an H+ from one of the hydroxyls to form a monophenolate ion or lose an H+ from both to form a diphenolate ion. Hydroquinone has a variety of uses principally associated with its action as a reducing agent which is soluble in water. It is a major component of most photographic developers where, with the compound Metol, it reduces silver halides to elemental silver.123-31-9C0053078517594236-TRICHLOROHYDROQUINONE764OC1=CC=C(O)C=C1C6H6O2InChI=1S/C6H6O2/c7-5-1-2-6(8)4-3-5/h1-4,7-8HQIGBRXMKCJKVMJ-UHFFFAOYSA-N110.1106110.036779436FDB0008851,4-benzenediol;1,4-dihydroxy-benzeen;1,4-dihydroxy-benzol;1,4-dihydroxybenzen;1,4-diidrobenzene;4-hydroxyphenol;Benzene-1,4-diol;Benzohydroquinone;Benzoquinol;Dihydroquinone;Dihydroxybenzene;Hydrochinon;Hydrochinone;Hydroquinol;Hydroquinole;Hydroquinone;Hydroquinone for synthesis;Hydroquinone gr;Hydroquinoue;Idrochinone;Melanex;Phiaquin;Quinol;Solaquin forte;A-hydroquinone;Alpha-hydroquinone;B-quinol;Beta-quinol;P-benzenediol;P-dihydroxybenzene;P-dioxobenzene;P-dioxybenzene;P-hydroquinone;P-hydroxybenzene;P-hydroxyphenol;1,4-dihydroxybenzene;EldoquinPW_C001632Quinol11833346232249013589495780321127805332978804343120759407120882415121416382123356119123458451123975399125791481127246206127304504964FADHMDB0001248FAD, also known as flavitan or adeflavin, belongs to the class of organic compounds known as flavin nucleotides. These are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. FAD is a drug which is used to treat eye diseases caused by vitamin b2 deficiency, such as keratitis and blepharitis. FAD is slightly soluble (in water) and a moderately acidic compound (based on its pKa). FAD has been found in human liver and muscle tissues, and has also been detected in multiple biofluids, such as feces and blood. Within the cell, FAD is primarily located in the cytoplasm, mitochondria, endoplasmic reticulum and peroxisome. FAD exists in all living organisms, ranging from bacteria to humans. In humans, FAD is involved in the risedronate action pathway, the ibandronate action pathway, the valine, leucine and isoleucine degradation pathway, and the pyrimidine metabolism pathway. FAD is also involved in several metabolic disorders, some of which include the oncogenic action OF L-2-hydroxyglutarate in hydroxygluaricaciduria pathway, gaba-transaminase deficiency, 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, and the saccharopinuria/hyperlysinemia II pathway. FAD is a condensation product of riboflavin and adenosine diphosphate. The coenzyme of various aerobic dehydrogenases, e.g., D-amino acid oxidase and L-amino acid oxidase. (Lehninger, Principles of Biochemistry, 1982, p972).146-14-5C0001664397516238FAD559059DB03147CC1=CC2=C(C=C1C)N(C[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC3=C1N=CN=C3N)C1=NC(=O)NC(=O)C1=N2C27H33N9O15P2InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1VWWQXMAJTJZDQX-UYBVJOGSSA-N785.5497785.157134455FDB0225111h-purin-6-amine flavin dinucleotide;1h-purin-6-amine flavine dinucleotide;Adenine-flavin dinucleotide;Adenine-flavine dinucleotide;Adenine-riboflavin dinuceotide;Adenine-riboflavin dinucleotide;Adenine-riboflavine dinucleotide;Fad;Flamitajin b;Flanin f;Flavin adenine dinucleotide;Flavin adenine dinucleotide oxidized;Flavin-adenine dinucleotide;Flavine adenosine diphosphate;Flavine-adenine dinucleotide;Flavitan;Flaziren;Isoalloxazine-adenine dinucleotide;Riboflavin 5'-adenosine diphosphate;Riboflavin-adenine dinucleotide;Riboflavine-adenine dinucleotide;AdeflavinPW_C000964FAD99911451868192321642531762828825188402118814148942161229162249213358253622372326460236468831474113475810488165268103528510253351115496126551112756131186030155605415660821616116162639016475178649917966661077039163717520573212137465222748722390762241181821611887215118992111229622512328249124431511251922712595226127102911272029213029301130413024362331877080293771261337715213477501113775071127751811577541334776151327772633778054329783753457893033179222336792723588001236880034369807141191199584061199993841200514081201074071204324051204531221204901241212784291212984181214173821214893831227481201227761211228023741228234431230663761230871351231664481238494641238684541239763991240473981253484791253784801254294821254744811256972971259794891261072991262774841268915011269203911269685021269872071270112061273102091274325061276023881278403891407901851407991862617Glycerate kinaseQ8IVS8HMDBP07384GLYCTK3p21.1AY18928612.7.1.31205383477214585011885Aldose reductaseP15121Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
HMDBP00088AKR1B17q35M3472011.1.1.2110078195323110913886229714395626781Glycerol kinaseP32189Key enzyme in the regulation of glycerol uptake and metabolism.
HMDBP00836GKXp21.3AC00591312.7.1.3020648782Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmicP21695HMDBP00837GPD112q12-q13AC02515411.1.1.81044814762138448198141821261445741284227Diacylglycerol kinase alphaP23743Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activityHMDBP00233DGKA12q13.3AF06477112.7.1.1071536142114102162581130418113448166138434211145783818286Aldehyde dehydrogenase, dimeric NADP-preferringP30838ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
HMDBP00292ALDH3A117p11.2M7747711.2.1.5131782015234027361929500231142964789143384261446681292783Glycerol-3-phosphate acyltransferase 1, mitochondrialQ9HCL2Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
HMDBP00838GPAM10q25.2AL39198612.3.1.151646320871021355846282213844916314691-Acyl-sn-glycerol-3-phosphate acyltransferase alphaQ99943Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
HMDBP01581AGPAT16p21.3CR81247812.3.1.5114814914954221081021415833431133521846212138420213138424756231Lipid phosphate phosphohydrolase 1O14494Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
HMDBP00237PPAP2A5q11AF01440213.1.3.4153914337918461910138435211192Glycerol-3-phosphate dehydrogenase, mitochondrialP43304HMDBP00197GPD22q24.1U4036211.1.5.3104731479491492422117584624221384237561445691285225Lipid phosphate phosphohydrolase 2O43688Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
HMDBP00231PPAP2C19p13AF04776013.1.3.4211010214458463022304Lipoprotein lipaseP06858The primary function of this lipase is the hydrolysis of triglycerides of circulating chylomicrons and very low density lipoproteins (VLDL). Binding to heparin sulfate proteogylcans at the cell surface is vital to the function. The apolipoprotein, APOC2, acts as a coactivator of LPL activity in the presence of lipids on the luminal surface of vascular endothelium (By similarity).
HMDBP00310LPL8p22CH47108013.1.1.342178142187152899813784671314321211231432582220Hepatic triacylglycerol lipaseP11150Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin.
HMDBP00226LIPC15q21-q23M2918813.1.1.321861546312535Glycerate kinase1PW_P0005355672617275Aldose reductase1PW_P000275294851542Glycerol kinase1PW_P000542574781293Glycerol-3-phosphate dehydrogenase [NAD(+)], cytoplasmic1PW_P000293312782224032417Diacylglycerol kinase alpha1PW_P000417439227371Aldehyde dehydrogenase, dimeric NADP-preferring1PW_P0003713932861448Glycerol-3-phosphate acyltransferase 1, mitochondrial1PW_P0004484717834021-acyl-sn-glycerol-3-phosphate acyltransferase alpha1PW_P0004024241469418Lipid phosphate phosphohydrolase 11PW_P000418440231292Glycerol-3-phosphate dehydrogenase, mitochondrial1PW_P00029231119211309641553Lipid phosphate phosphohydrolase 21PW_P0005535942252240414565Lipoprotein lipase1PW_P000565606304568Hepatic triacylglycerol 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