Chemical Formula: C43H79O9P

Chemical Formula C43H79O9P

Found 93 metabolite its formula value is C43H79O9P

PA(20:0/20:3(6,8,11)-OH(5))

[(2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-(icosanoyloxy)propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(20:0/20:3(6,8,11)-OH(5)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(20:0/20:3(6,8,11)-OH(5)), in particular, consists of one chain of one eicosanoyl at the C-1 position and one chain of 5-hydroxyeicosatetrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(20:3(6,8,11)-OH(5)/20:0)

[(2R)-3-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-2-(icosanoyloxy)propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(20:3(6,8,11)-OH(5)/20:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(20:3(6,8,11)-OH(5)/20:0), in particular, consists of one chain of one 5-hydroxyeicosatetrienoyl at the C-1 position and one chain of eicosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:0/18:2(10E,12Z)+=O(9))

[(2R)-3-(docosanoyloxy)-2-{[(10E,12Z)-9-oxooctadeca-10,12-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:0/18:2(10E,12Z)+=O(9)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:0/18:2(10E,12Z)+=O(9)), in particular, consists of one chain of one docosanoyl at the C-1 position and one chain of 9-oxo-octadecadienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:2(10E,12Z)+=O(9)/22:0)

[(2R)-2-(docosanoyloxy)-3-{[(10E,12Z)-9-oxooctadeca-10,12-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:2(10E,12Z)+=O(9)/22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:2(10E,12Z)+=O(9)/22:0), in particular, consists of one chain of one 9-oxo-octadecadienoyl at the C-1 position and one chain of docosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:0/18:2(9Z,11E)+=O(13))

[(2R)-3-(docosanoyloxy)-2-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:0/18:2(9Z,11E)+=O(13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:0/18:2(9Z,11E)+=O(13)), in particular, consists of one chain of one docosanoyl at the C-1 position and one chain of 13-oxo-octadecadienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:2(9Z,11E)+=O(13)/22:0)

[(2R)-2-(docosanoyloxy)-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:2(9Z,11E)+=O(13)/22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:2(9Z,11E)+=O(13)/22:0), in particular, consists of one chain of one 13-oxo-octadecadienoyl at the C-1 position and one chain of docosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:0/18:3(10,12,15)-OH(9))

[(2R)-3-(docosanoyloxy)-2-{[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:0/18:3(10,12,15)-OH(9)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:0/18:3(10,12,15)-OH(9)), in particular, consists of one chain of one docosanoyl at the C-1 position and one chain of 9-hydroxyoctadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:3(10,12,15)-OH(9)/22:0)

[(2R)-2-(docosanoyloxy)-3-{[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:3(10,12,15)-OH(9)/22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:3(10,12,15)-OH(9)/22:0), in particular, consists of one chain of one 9-hydroxyoctadecatrienoyl at the C-1 position and one chain of docosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:0/18:3(9,11,15)-OH(13))

[(2R)-3-(docosanoyloxy)-2-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:0/18:3(9,11,15)-OH(13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:0/18:3(9,11,15)-OH(13)), in particular, consists of one chain of one docosanoyl at the C-1 position and one chain of 13-hydroxyoctadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:3(9,11,15)-OH(13)/22:0)

[(2R)-2-(docosanoyloxy)-3-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:3(9,11,15)-OH(13)/22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:3(9,11,15)-OH(13)/22:0), in particular, consists of one chain of one 13-hydroxyoctadecatrienoyl at the C-1 position and one chain of docosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:1(13Z)/18:1(12Z)-O(9S,10R))

[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:1(13Z)/18:1(12Z)-O(9S,10R)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:1(13Z)/18:1(12Z)-O(9S,10R)), in particular, consists of one chain of one 13Z-docosenoyl at the C-1 position and one chain of 9,10-epoxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:1(12Z)-O(9S,10R)/22:1(13Z))

[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:1(12Z)-O(9S,10R)/22:1(13Z)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:1(12Z)-O(9S,10R)/22:1(13Z)), in particular, consists of one chain of one 9,10-epoxy-octadecenoyl at the C-1 position and one chain of 13Z-docosenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:1(13Z)/18:1(9Z)-O(12,13))

[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(22:1(13Z)/18:1(9Z)-O(12,13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(22:1(13Z)/18:1(9Z)-O(12,13)), in particular, consists of one chain of one 13Z-docosenoyl at the C-1 position and one chain of 12,13-epoxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:1(9Z)-O(12,13)/22:1(13Z))

[(2R)-2-[(13Z)-docos-13-enoyloxy]-3-{[(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:1(9Z)-O(12,13)/22:1(13Z)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:1(9Z)-O(12,13)/22:1(13Z)), in particular, consists of one chain of one 12,13-epoxy-octadecenoyl at the C-1 position and one chain of 13Z-docosenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(i-20:0/20:3(6,8,11)-OH(5))

[(2R)-2-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-3-[(18-methylnonadecanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(i-20:0/20:3(6,8,11)-OH(5)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(i-20:0/20:3(6,8,11)-OH(5)), in particular, consists of one chain of one 18-methylnonadecanoyl at the C-1 position and one chain of 5-hydroxyeicosatetrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(20:3(6,8,11)-OH(5)/i-20:0)

[(2R)-3-{[(6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoyl]oxy}-2-[(18-methylnonadecanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(20:3(6,8,11)-OH(5)/i-20:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(20:3(6,8,11)-OH(5)/i-20:0), in particular, consists of one chain of one 5-hydroxyeicosatetrienoyl at the C-1 position and one chain of 18-methylnonadecanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(i-22:0/18:2(10E,12Z)+=O(9))

[(2R)-3-[(20-methylhenicosanoyl)oxy]-2-{[(10E,12Z)-9-oxooctadeca-10,12-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(i-22:0/18:2(10E,12Z)+=O(9)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(i-22:0/18:2(10E,12Z)+=O(9)), in particular, consists of one chain of one 20-methylheneicosanoyl at the C-1 position and one chain of 9-oxo-octadecadienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:2(10E,12Z)+=O(9)/i-22:0)

[(2R)-2-[(20-methylhenicosanoyl)oxy]-3-{[(10E,12Z)-9-oxooctadeca-10,12-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:2(10E,12Z)+=O(9)/i-22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:2(10E,12Z)+=O(9)/i-22:0), in particular, consists of one chain of one 9-oxo-octadecadienoyl at the C-1 position and one chain of 20-methylheneicosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(i-22:0/18:2(9Z,11E)+=O(13))

[(2R)-3-[(20-methylhenicosanoyl)oxy]-2-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(i-22:0/18:2(9Z,11E)+=O(13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(i-22:0/18:2(9Z,11E)+=O(13)), in particular, consists of one chain of one 20-methylheneicosanoyl at the C-1 position and one chain of 13-oxo-octadecadienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:2(9Z,11E)+=O(13)/i-22:0)

[(2R)-2-[(20-methylhenicosanoyl)oxy]-3-{[(9Z,11E)-13-oxooctadeca-9,11-dienoyl]oxy}propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:2(9Z,11E)+=O(13)/i-22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:2(9Z,11E)+=O(13)/i-22:0), in particular, consists of one chain of one 13-oxo-octadecadienoyl at the C-1 position and one chain of 20-methylheneicosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(i-22:0/18:3(10,12,15)-OH(9))

[(2R)-2-{[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy}-3-[(20-methylhenicosanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(i-22:0/18:3(10,12,15)-OH(9)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(i-22:0/18:3(10,12,15)-OH(9)), in particular, consists of one chain of one 20-methylheneicosanoyl at the C-1 position and one chain of 9-hydroxyoctadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:3(10,12,15)-OH(9)/i-22:0)

[(2R)-3-{[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:3(10,12,15)-OH(9)/i-22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:3(10,12,15)-OH(9)/i-22:0), in particular, consists of one chain of one 9-hydroxyoctadecatrienoyl at the C-1 position and one chain of 20-methylheneicosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(i-22:0/18:3(9,11,15)-OH(13))

[(2R)-2-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}-3-[(20-methylhenicosanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(i-22:0/18:3(9,11,15)-OH(13)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(i-22:0/18:3(9,11,15)-OH(13)), in particular, consists of one chain of one 20-methylheneicosanoyl at the C-1 position and one chain of 13-hydroxyoctadecatrienoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(18:3(9,11,15)-OH(13)/i-22:0)

[(2R)-3-{[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy}-2-[(20-methylhenicosanoyl)oxy]propoxy]phosphonic acid

C43H79O9P (770.5461)


PA(18:3(9,11,15)-OH(13)/i-22:0) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(18:3(9,11,15)-OH(13)/i-22:0), in particular, consists of one chain of one 13-hydroxyoctadecatrienoyl at the C-1 position and one chain of 20-methylheneicosanoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).

   

PA(22:0/18:2(10E,12Z)+=O(9))

PA(22:0/18:2(10E,12Z)+=O(9))

C43H79O9P (770.5461)


   

PA(18:2(10E,12Z)+=O(9)/22:0)

PA(18:2(10E,12Z)+=O(9)/22:0)

C43H79O9P (770.5461)


   

PA(22:0/18:2(9Z,11E)+=O(13))

PA(22:0/18:2(9Z,11E)+=O(13))

C43H79O9P (770.5461)


   

PA(18:2(9Z,11E)+=O(13)/22:0)

PA(18:2(9Z,11E)+=O(13)/22:0)

C43H79O9P (770.5461)


   

PA(i-20:0/20:3(6,8,11)-OH(5))

PA(i-20:0/20:3(6,8,11)-OH(5))

C43H79O9P (770.5461)


   

PA(20:3(6,8,11)-OH(5)/i-20:0)

PA(20:3(6,8,11)-OH(5)/i-20:0)

C43H79O9P (770.5461)


   

PA(i-22:0/18:2(10E,12Z)+=O(9))

PA(i-22:0/18:2(10E,12Z)+=O(9))

C43H79O9P (770.5461)


   

PA(18:2(10E,12Z)+=O(9)/i-22:0)

PA(18:2(10E,12Z)+=O(9)/i-22:0)

C43H79O9P (770.5461)


   

PA(i-22:0/18:2(9Z,11E)+=O(13))

PA(i-22:0/18:2(9Z,11E)+=O(13))

C43H79O9P (770.5461)


   

PA(18:2(9Z,11E)+=O(13)/i-22:0)

PA(18:2(9Z,11E)+=O(13)/i-22:0)

C43H79O9P (770.5461)


   

[(2R)-1-icosanoyloxy-3-phosphonooxypropan-2-yl] (6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoate

[(2R)-1-icosanoyloxy-3-phosphonooxypropan-2-yl] (6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoate

C43H79O9P (770.5461)


   

[(2R)-2-icosanoyloxy-3-phosphonooxypropyl] (6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoate

[(2R)-2-icosanoyloxy-3-phosphonooxypropyl] (6E,8E,11E)-5-hydroxyicosa-6,8,11-trienoate

C43H79O9P (770.5461)


   

[(2R)-2-[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy-3-phosphonooxypropyl] docosanoate

[(2R)-2-[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy-3-phosphonooxypropyl] docosanoate

C43H79O9P (770.5461)


   

[(2R)-1-[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy-3-phosphonooxypropan-2-yl] docosanoate

[(2R)-1-[(10E,12E,15E)-9-hydroxyoctadeca-10,12,15-trienoyl]oxy-3-phosphonooxypropan-2-yl] docosanoate

C43H79O9P (770.5461)


   

[(2R)-2-[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy-3-phosphonooxypropyl] docosanoate

[(2R)-2-[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy-3-phosphonooxypropyl] docosanoate

C43H79O9P (770.5461)


   

[(2R)-1-[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy-3-phosphonooxypropan-2-yl] docosanoate

[(2R)-1-[(9E,11E,15E)-13-hydroxyoctadeca-9,11,15-trienoyl]oxy-3-phosphonooxypropan-2-yl] docosanoate

C43H79O9P (770.5461)


   

PA(22:1(13Z)/18:1(12Z)-O(9S,10R))

PA(22:1(13Z)/18:1(12Z)-O(9S,10R))

C43H79O9P (770.5461)


   

PA(18:1(12Z)-O(9S,10R)/22:1(13Z))

PA(18:1(12Z)-O(9S,10R)/22:1(13Z))

C43H79O9P (770.5461)


   

PA(22:1(13Z)/18:1(9Z)-O(12,13))

PA(22:1(13Z)/18:1(9Z)-O(12,13))

C43H79O9P (770.5461)


   

PA(18:1(9Z)-O(12,13)/22:1(13Z))

PA(18:1(9Z)-O(12,13)/22:1(13Z))

C43H79O9P (770.5461)


   

PA(i-22:0/18:3(10,12,15)-OH(9))

PA(i-22:0/18:3(10,12,15)-OH(9))

C43H79O9P (770.5461)


   

PA(18:3(10,12,15)-OH(9)/i-22:0)

PA(18:3(10,12,15)-OH(9)/i-22:0)

C43H79O9P (770.5461)


   

PA(i-22:0/18:3(9,11,15)-OH(13))

PA(i-22:0/18:3(9,11,15)-OH(13))

C43H79O9P (770.5461)


   

PA(18:3(9,11,15)-OH(13)/i-22:0)

PA(18:3(9,11,15)-OH(13)/i-22:0)

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-henicosoxypropan-2-yl] (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-henicosoxypropan-2-yl] (4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-tridec-9-enoxy]propan-2-yl] (10Z,13Z,16Z)-tetracosa-10,13,16-trienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-tridec-9-enoxy]propan-2-yl] (10Z,13Z,16Z)-tetracosa-10,13,16-trienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z)-icosa-11,14-dienoxy]propan-2-yl] (9Z,12Z)-heptadeca-9,12-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z)-icosa-11,14-dienoxy]propan-2-yl] (9Z,12Z)-heptadeca-9,12-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-henicos-11-enoxy]propan-2-yl] (7Z,10Z,13Z)-hexadeca-7,10,13-trienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-henicos-11-enoxy]propan-2-yl] (7Z,10Z,13Z)-hexadeca-7,10,13-trienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-tridecoxypropan-2-yl] (12Z,15Z,18Z,21Z)-tetracosa-12,15,18,21-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-tridecoxypropan-2-yl] (12Z,15Z,18Z,21Z)-tetracosa-12,15,18,21-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-nonadec-9-enoxy]propan-2-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-nonadec-9-enoxy]propan-2-yl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-heptadecoxypropan-2-yl] (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-heptadecoxypropan-2-yl] (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoxy]propan-2-yl] nonadecanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoxy]propan-2-yl] nonadecanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoxy]propan-2-yl] heptadecanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoxy]propan-2-yl] heptadecanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoxy]propan-2-yl] henicosanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoxy]propan-2-yl] henicosanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z)-tetracosa-10,13,16-trienoxy]propan-2-yl] (Z)-tridec-9-enoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z)-tetracosa-10,13,16-trienoxy]propan-2-yl] (Z)-tridec-9-enoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-nonadeca-9,12-dienoxy]propan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-nonadeca-9,12-dienoxy]propan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z,19Z)-docosa-10,13,16,19-tetraenoxy]propan-2-yl] pentadecanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z,19Z)-docosa-10,13,16,19-tetraenoxy]propan-2-yl] pentadecanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-pentadec-9-enoxy]propan-2-yl] (10Z,13Z,16Z)-docosa-10,13,16-trienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-pentadec-9-enoxy]propan-2-yl] (10Z,13Z,16Z)-docosa-10,13,16-trienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-undecoxypropan-2-yl] (14Z,17Z,20Z,23Z)-hexacosa-14,17,20,23-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-undecoxypropan-2-yl] (14Z,17Z,20Z,23Z)-hexacosa-14,17,20,23-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-heptadeca-9,12-dienoxy]propan-2-yl] (11Z,14Z)-icosa-11,14-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-heptadeca-9,12-dienoxy]propan-2-yl] (11Z,14Z)-icosa-11,14-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z)-docosa-10,13,16-trienoxy]propan-2-yl] (Z)-pentadec-9-enoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(10Z,13Z,16Z)-docosa-10,13,16-trienoxy]propan-2-yl] (Z)-pentadec-9-enoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z,17Z)-icosa-11,14,17-trienoxy]propan-2-yl] (Z)-heptadec-9-enoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z,17Z)-icosa-11,14,17-trienoxy]propan-2-yl] (Z)-heptadec-9-enoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-nonadecoxypropan-2-yl] (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-nonadecoxypropan-2-yl] (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoxy]propan-2-yl] (Z)-henicos-11-enoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(7Z,10Z,13Z)-hexadeca-7,10,13-trienoxy]propan-2-yl] (Z)-henicos-11-enoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z)-henicosa-11,14-dienoxy]propan-2-yl] (9Z,12Z)-hexadeca-9,12-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(11Z,14Z)-henicosa-11,14-dienoxy]propan-2-yl] (9Z,12Z)-hexadeca-9,12-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-octadeca-9,12-dienoxy]propan-2-yl] (9Z,12Z)-nonadeca-9,12-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-octadeca-9,12-dienoxy]propan-2-yl] (9Z,12Z)-nonadeca-9,12-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-heptadec-9-enoxy]propan-2-yl] (11Z,14Z,17Z)-icosa-11,14,17-trienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(Z)-heptadec-9-enoxy]propan-2-yl] (11Z,14Z,17Z)-icosa-11,14,17-trienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-pentadecoxypropan-2-yl] (10Z,13Z,16Z,19Z)-docosa-10,13,16,19-tetraenoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-pentadecoxypropan-2-yl] (10Z,13Z,16Z,19Z)-docosa-10,13,16,19-tetraenoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(14Z,17Z,20Z,23Z)-hexacosa-14,17,20,23-tetraenoxy]propan-2-yl] undecanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(14Z,17Z,20Z,23Z)-hexacosa-14,17,20,23-tetraenoxy]propan-2-yl] undecanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-hexadeca-9,12-dienoxy]propan-2-yl] (11Z,14Z)-henicosa-11,14-dienoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z)-hexadeca-9,12-dienoxy]propan-2-yl] (11Z,14Z)-henicosa-11,14-dienoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(12Z,15Z,18Z,21Z)-tetracosa-12,15,18,21-tetraenoxy]propan-2-yl] tridecanoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(12Z,15Z,18Z,21Z)-tetracosa-12,15,18,21-tetraenoxy]propan-2-yl] tridecanoate

C43H79O9P (770.5461)


   

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoxy]propan-2-yl] (Z)-nonadec-9-enoate

[1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoxy]propan-2-yl] (Z)-nonadec-9-enoate

C43H79O9P (770.5461)


   

PA O-20:0/20:4;O2

PA O-20:0/20:4;O2

C43H79O9P (770.5461)


   
   

PA P-20:0/20:3;O2

PA P-20:0/20:3;O2

C43H79O9P (770.5461)


   

PA 20:0/20:3;O

PA 20:0/20:3;O

C43H79O9P (770.5461)


   

PA 20:1/20:2;O

PA 20:1/20:2;O

C43H79O9P (770.5461)


   

PA 22:0/18:3;O

PA 22:0/18:3;O

C43H79O9P (770.5461)


   

PA 22:1/18:2;O

PA 22:1/18:2;O

C43H79O9P (770.5461)


   

PA 22:2/18:1;O

PA 22:2/18:1;O

C43H79O9P (770.5461)


   
   

PG O-20:2/17:2

PG O-20:2/17:2

C43H79O9P (770.5461)


   
   

PG P-20:1/17:2

PG P-20:1/17:2

C43H79O9P (770.5461)


   

PG P-20:1/17:2 or PG O-20:2/17:2

PG P-20:1/17:2 or PG O-20:2/17:2

C43H79O9P (770.5461)


   
   

PG P-37:3 or PG O-37:4

PG P-37:3 or PG O-37:4

C43H79O9P (770.5461)