1.02011-09-21 00:34:10 UTC2015-07-21 06:57:50 UTCFDB023751TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))TG(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) is a triarachidonic acid triglyceride. Triglycerides (TGs) 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 tri-esters 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(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of arachidonic acid at the C-1 position, one chain of arachidonic acid at the C-2 position and one chain of arachidonic 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)
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. [HMDB]1-arachidonoyl-2-arachidonoyl-3-arachidonoyl-glycerolTAG(20:4/20:4/20:4)TAG(20:4n6/20:4n6/20:4n6)TAG(20:4w6/20:4w6/20:4w6)TAG(60:12)TG(20:4/20:4/20:4)TG(20:4n6/20:4n6/20:4n6)TG(20:4w6/20:4w6/20:4w6)TG(60:12)Tracylglycerol(20:4/20:4/20:4)Tracylglycerol(20:4n6/20:4n6/20:4n6)Tracylglycerol(20:4w6/20:4w6/20:4w6)Tracylglycerol(60:12)C63H98O6951.4486950.7363408681,3-bis(icosa-5,8,11,14-tetraenoyloxy)propan-2-yl icosa-5,8,11,14-tetraenoate1,3-bis(icosa-5,8,11,14-tetraenoyloxy)propan-2-yl icosa-5,8,11,14-tetraenoateCCCCCC=CCC=CCC=CCC=CCCCC(=O)OCC(COC(=O)CCCC=CCC=CCC=CCC=CCCCCC)OC(=O)CCCC=CCC=CCC=CCC=CCCCCCInChI=1S/C63H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-52-55-61(64)67-58-60(69-63(66)57-54-51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)59-68-62(65)56-53-50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,34-39,43-48,60H,4-15,22-24,31-33,40-42,49-59H2,1-3H3HYVJNYYVNIYMDK-UHFFFAOYSA-N belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.TriacylglycerolsOrganic compoundsLipids and lipid-like moleculesGlycerolipidsTriradylcglycerolsAliphatic acyclic compoundsCarbonyl compoundsCarboxylic acid estersFatty acid estersHydrocarbon derivativesOrganic oxidesTricarboxylic acids and derivativesAliphatic acyclic compoundCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterFatty acid esterFatty acylHydrocarbon derivativeOrganic oxideOrganic oxygen compoundOrganooxygen compoundTriacyl-sn-glycerolTricarboxylic acid or derivativesSolidlogp9.75logs-8.13solubility7.06e-06 g/llogp19.92pka_strongest_basic-6.6iupac1,3-bis(icosa-5,8,11,14-tetraenoyloxy)propan-2-yl icosa-5,8,11,14-tetraenoateaverage_mass951.4486mono_mass950.736340868smilesCCCCCC=CCC=CCC=CCC=CCCCC(=O)OCC(COC(=O)CCCC=CCC=CCC=CCC=CCCCCC)OC(=O)CCCC=CCC=CCC=CCC=CCCCCCformulaC63H98O6inchiInChI=1S/C63H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-52-55-61(64)67-58-60(69-63(66)57-54-51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)59-68-62(65)56-53-50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,34-39,43-48,60H,4-15,22-24,31-33,40-42,49-59H2,1-3H3inchikeyHYVJNYYVNIYMDK-UHFFFAOYSA-Npolar_surface_area78.9refractivity309.9polarizability117.55rotatable_bond_count50acceptor_count3donor_count0physiological_charge0formal_charge0HMDB05478AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa98232-acylglycerol O-acyltransferase 1Q96PD6MOGAT12-acylglycerol O-acyltransferase 2Q3SYC2MOGAT22-acylglycerol O-acyltransferase 3Q86VF5MOGAT3Apolipoprotein A-IP02647APOA1Apolipoprotein B-100P04114APOBApolipoprotein EP02649APOECarnitine O-palmitoyltransferase 1, liver isoformP50416CPT1ACarnitine O-palmitoyltransferase 1, muscle isoformQ92523CPT1BCarnitine O-palmitoyltransferase 2, mitochondrialP23786CPT2Diacylglycerol O-acyltransferase 1O75907DGAT1Diacylglycerol O-acyltransferase 2Q96PD7DGAT2Endothelial lipaseQ9Y5X9LIPGGastric triacylglycerol lipaseP07098LIPFGlycerol-3-phosphate acyltransferase 3Q53EU6AGPAT9Hepatic triacylglycerol lipaseP11150LIPCInactive pancreatic lipase-related protein 1P54315PNLIPRP1Lipoprotein lipaseP06858LPLLiver carboxylesterase 1P23141CES1Lysosomal acid lipase/cholesteryl ester hydrolaseP38571LIPAMonoglyceride lipaseQ99685MGLLPancreatic lipase-related protein 2P54317PNLIPRP2Pancreatic lipase-related protein 3Q17RR3PNLIPRP3Pancreatic triacylglycerol lipaseP16233PNLIPPatatin-like phospholipase domain-containing protein 2Q96AD5PNPLA2Patatin-like phospholipase domain-containing protein 3Q9NST1PNPLA3Patatin-like phospholipase domain-containing protein 4P41247PNPLA4Protein disulfide-isomeraseP07237P4HB