FoodTCM

pg(18:3(6z,9z,12z)/18:3(9z,12z,15z))

Name(s)	pg(18:3(6z,9z,12z)/18:3(9z,12z,15z))
Scientific name(s)
Formula	C42H71O10P
Molecular mass	766.9809
IUPAC name	[(2S)-2,3-dihydroxypropoxy][(2R)-3-(octadeca-6,9,12-trienoyloxy)-2-(octadeca-9,12,15-trienoyloxy)propoxy]phosphinic acid
INCHI	InChI=1S/C42H71O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-41(45)49-37-40(38-51-53(47,48)50-36-39(44)35-43)52-42(46)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h6,8,11-14,17-20,23,25,39-40,43-44H,3-5,7,9-10,15-16,21-22,24,26-38H2,1-2H3,(H,47,48)/t39-,40+/m0/s1
SMILE	[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCC=CCC=CCC=CCCCCC)OC(=O)CCCCCCCC=CCC=CCC=CCC
CAS ID	Not available
PubChem ID	52926646
DrugBank ID	Not available
CHEBI ID	Not available

Description	PG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB]

Description

PG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:3(6Z,9Z,12Z)/18:3(9Z,12Z,15Z)), in particular, consists of one chain of g-linolenic acid at the C-1 position and one chain of a-linolenic acid at the C-2 position. The g-linolenic acid moiety is derived from animal fats, while the a-linolenic acid moiety is derived from seed oils, especially canola and soybean oil. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB]