Exact Mass: 625.338

Exact Mass Matches: 625.338

Found 68 metabolites which its exact mass value is equals to given mass value 625.338, within given mass tolerance error 0.01 dalton. Try search metabolite list with more accurate mass tolerance error 0.001 dalton.

Glycochenodeoxycholic acid 3-glucuronide

(2S,3S,4S,5R,6R)-6-[[(3R,5R,7R,8R,9S,10S,13R,14S)-17-[(2R)-5-(carboxymethylamino)-5-oxopentan-2-yl]-7-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

C32H51NO11 (625.3462)


Glycochenodeoxycholic acid (GCDC)induced the mitochondrial permeability transition (MPT) in a dose-dependent manner, which was inhibited by cyclosporin A, alpha-tocopherol, beta-carotene and idebenone. GCDC stimulated reactive oxygen species generation and release of cytochrome c and apoptosis-inducing factor, which were significantly inhibited by the antioxidants, cyclosporin A, and tauroursodeoxycholic acid. mitochondrial pathways of cell death are stimulated in human hepatic mitochondria exposed to GCDC consistent with the role of mitochondrial dysfunction in the pathogenesis of cholestatic liver injury. (16056106) [HMDB] Glycochenodeoxycholic acid (GCDC)induced the mitochondrial permeability transition (MPT) in a dose-dependent manner, which was inhibited by cyclosporin A, alpha-tocopherol, beta-carotene and idebenone. GCDC stimulated reactive oxygen species generation and release of cytochrome c and apoptosis-inducing factor, which were significantly inhibited by the antioxidants, cyclosporin A, and tauroursodeoxycholic acid. mitochondrial pathways of cell death are stimulated in human hepatic mitochondria exposed to GCDC consistent with the role of mitochondrial dysfunction in the pathogenesis of cholestatic liver injury. (16056106).

   

Methyl 6-[(3S,6S,9S,12R)-3-butan-2-yl-6-[(1-methoxyindol-3-yl)methyl]-2,5,8,11-tetraoxo-1,4,7,10-tetrazabicyclo[10.4.0]hexadecan-9-yl]hexanoate

Methyl 6-[9-(butan-2-yl)-1,4,7-trihydroxy-6-[(1-methoxy-1H-indol-3-yl)methyl]-10-oxo-3H,6H,9H,10H,12H,13H,14H,15H,15ah-pyrido[1,2-a]1,4,7,10-tetraazacyclododecan-3-yl]hexanoic acid

C33H47N5O7 (625.3475)


   

[4-[(2R)-7-(2,2-Dimethylpropanoyloxy)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2H-chromen-3-yl]phenyl] 2,2-dimethylpropanoate

[4-[(2R)-7-(2,2-Dimethylpropanoyloxy)-4-methyl-2-[4-(2-piperidin-1-ylethoxy)phenyl]-2H-chromen-3-yl]phenyl] 2,2-dimethylpropanoic acid

C39H47NO6 (625.3403)


   

PC(2:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4))

(2-{[(2R)-3-(acetyloxy)-2-{[(5Z,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(2:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(2:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 4-hydroxy-docosahexaenoyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)/2:0)

(2-{[(2R)-2-(acetyloxy)-3-{[(5Z,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)/2:0) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)/2:0), in particular, consists of one chain of one 4-hydroxy-docosahexaenoyl at the C-1 position and one chain of acetyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(2:0/22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7))

(2-{[(2R)-3-(acetyloxy)-2-{[(4Z,8Z,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(2:0/22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(2:0/22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 7-hydroxy-docosahexaenoyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)/2:0)

(2-{[(2R)-2-(acetyloxy)-3-{[(4Z,8Z,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)/2:0) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)/2:0), in particular, consists of one chain of one 7-hydroxy-docosahexaenoyl at the C-1 position and one chain of acetyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(2:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14))

(2-{[(2R)-3-(acetyloxy)-2-{[(4Z,7Z,10Z,12E,16Z,19Z)-14-hydroxydocosa-4,7,10,12,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(2:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(2:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 14-hydroxy-docosahexaenoyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)/2:0)

(2-{[(2R)-2-(acetyloxy)-3-{[(4Z,7Z,10Z,12E,16Z,19Z)-14-hydroxydocosa-4,7,10,12,16,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)/2:0) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)/2:0), in particular, consists of one chain of one 14-hydroxy-docosahexaenoyl at the C-1 position and one chain of acetyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(2:0/22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17))

(2-{[(2R)-3-(acetyloxy)-2-{[(4Z,7Z,10Z,13E,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(2:0/22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(2:0/22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 17-hydroxy-docosahexaenoyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)/2:0)

(2-{[(2R)-2-(acetyloxy)-3-{[(4Z,7Z,10Z,13E,15E,19Z)-17-hydroxydocosa-4,7,10,13,15,19-hexaenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)/2:0) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)/2:0), in particular, consists of one chain of one 17-hydroxy-docosahexaenoyl at the C-1 position and one chain of acetyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(2:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17))

(2-{[(2R)-3-(acetyloxy)-2-{[(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(2:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(2:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)), in particular, consists of one chain of one acetyl at the C-1 position and one chain of 16,17-epoxy-docosapentaenoyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   

PC(22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)/2:0)

(2-{[(2R)-2-(acetyloxy)-3-{[(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

C32H52NO9P (625.338)


PC(22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)/2:0) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines 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, glycerophosphocholines 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. PC(22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)/2:0), in particular, consists of one chain of one 16,17-epoxy-docosapentaenoyl at the C-1 position and one chain of acetyl 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 PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396).

   
   

cyclo(Pro1-Gly2-Leu3-Ser4-Ala5-Val6-Thr7-)|cyclosenegalin A

cyclo(Pro1-Gly2-Leu3-Ser4-Ala5-Val6-Thr7-)|cyclosenegalin A

C28H47N7O9 (625.3435)


   

His Lys Arg Trp

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

His Lys Trp Arg

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]hexanamido]-3-(1H-indol-3-yl)propanamido]-5-carbamimidamidopentanoic acid

C29H43N11O5 (625.3448)


   

His Arg Lys Trp

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]hexanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

His Arg Trp Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

His Trp Lys Arg

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]hexanamido]-5-carbamimidamidopentanoic acid

C29H43N11O5 (625.3448)


   

His Trp Arg Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-5-carbamimidamidopentanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

Lys His Arg Trp

(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-imidazol-4-yl)propanamido]pentanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Lys His Trp Arg

(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]pentanoic acid

C29H43N11O5 (625.3448)


   

Lys Arg His Trp

(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Lys Arg Trp His

(2S)-2-[(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2,6-diaminohexanamido]pentanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Lys Trp His Arg

(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]pentanoic acid

C29H43N11O5 (625.3448)


   

Lys Trp Arg His

(2S)-2-[(2S)-5-carbamimidamido-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(1H-indol-3-yl)propanamido]pentanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Arg His Lys Trp

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]hexanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Arg His Trp Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

Arg Lys His Trp

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-3-(1H-imidazol-4-yl)propanamido]-3-(1H-indol-3-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Arg Lys Trp His

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-5-carbamimidamidopentanamido]hexanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Arg Trp His Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

Arg Trp Lys His

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-(1H-indol-3-yl)propanamido]hexanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Trp His Lys Arg

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]hexanamido]-5-carbamimidamidopentanoic acid

C29H43N11O5 (625.3448)


   

Trp His Arg Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

Trp Lys His Arg

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]hexanamido]-3-(1H-imidazol-4-yl)propanamido]-5-carbamimidamidopentanoic acid

C29H43N11O5 (625.3448)


   

Trp Lys Arg His

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]hexanamido]-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Trp Arg His Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-5-carbamimidamidopentanamido]-3-(1H-imidazol-4-yl)propanamido]hexanoic acid

C29H43N11O5 (625.3448)


   

Trp Arg Lys His

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-5-carbamimidamidopentanamido]hexanamido]-3-(1H-imidazol-4-yl)propanoic acid

C29H43N11O5 (625.3448)


   

Glycochenodeoxycholic acid 3-glucuronide

Glycochenodeoxycholic acid 3-glucuronide

C32H51NO11 (625.3462)


   

(3a,5b,7b)-24-[(carboxymethyl)amino]-7-hydroxy-24-oxocholan-3-yl-b-D-glucopyranosiduronic acid,

(3a,5b,7b)-24-[(carboxymethyl)amino]-7-hydroxy-24-oxocholan-3-yl-b-D-glucopyranosiduronic acid,

C32H51NO11 (625.3462)


   

PC(2:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4))

PC(2:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4))

C32H52NO9P (625.338)


   

PC(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)/2:0)

PC(22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)/2:0)

C32H52NO9P (625.338)


   

PC(2:0/22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7))

PC(2:0/22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7))

C32H52NO9P (625.338)


   

PC(22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)/2:0)

PC(22:6(4Z,8Z,10Z,13Z,16Z,19Z)-OH(7)/2:0)

C32H52NO9P (625.338)


   

PC(2:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14))

PC(2:0/22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14))

C32H52NO9P (625.338)


   

PC(22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)/2:0)

PC(22:6(4Z,7Z,10Z,12E,16Z,19Z)-OH(14)/2:0)

C32H52NO9P (625.338)


   

PC(2:0/22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17))

PC(2:0/22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17))

C32H52NO9P (625.338)


   

PC(22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)/2:0)

PC(22:6(4Z,7Z,10Z,13E,15E,19Z)-OH(17)/2:0)

C32H52NO9P (625.338)


   

PC(2:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17))

PC(2:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17))

C32H52NO9P (625.338)


   

PC(22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)/2:0)

PC(22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)/2:0)

C32H52NO9P (625.338)


   

cyclo[DL-Asu(OMe)-DL-Trp(OMe)-DL-xiIle-DL-Pip]

cyclo[DL-Asu(OMe)-DL-Trp(OMe)-DL-xiIle-DL-Pip]

C33H47N5O7 (625.3475)


   

Boc-DON-Gln-Ile-Val-OMe

Boc-DON-Gln-Ile-Val-OMe

C28H47N7O9 (625.3435)


   

PC 18:4/6:2;O

PC 18:4/6:2;O

C32H52NO9P (625.338)


   

PC 20:5/4:1;O

PC 20:5/4:1;O

C32H52NO9P (625.338)


   
   
   
   

PE P-18:1/9:5;O2

PE P-18:1/9:5;O2

C32H52NO9P (625.338)


   

PE 20:3/7:3;O

PE 20:3/7:3;O

C32H52NO9P (625.338)


   

PE 22:5/5:1;O

PE 22:5/5:1;O

C32H52NO9P (625.338)


   
   
   

ST 24:2;O6;HexNAc

ST 24:2;O6;HexNAc

C32H51NO11 (625.3462)


   

(6s,9s,12s,15s,18s,23as)-1,4,7,10,13,16-hexahydroxy-18-[(1r)-1-hydroxyethyl]-9-(hydroxymethyl)-15-isopropyl-12-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,22h,23h,23ah-pyrrolo[1,2-a]1,4,7,10,13,16,19-heptaazacyclohenicosan-19-one

(6s,9s,12s,15s,18s,23as)-1,4,7,10,13,16-hexahydroxy-18-[(1r)-1-hydroxyethyl]-9-(hydroxymethyl)-15-isopropyl-12-methyl-6-(2-methylpropyl)-3h,6h,9h,12h,15h,18h,21h,22h,23h,23ah-pyrrolo[1,2-a]1,4,7,10,13,16,19-heptaazacyclohenicosan-19-one

C28H47N7O9 (625.3435)


   

(2e,4e,11r)-12-[(4s,4ar,6r,8s,8ar)-4-{[(2r)-1,2-dihydroxy-2-[(2r,5r,6r)-2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4-dienoic acid

(2e,4e,11r)-12-[(4s,4ar,6r,8s,8ar)-4-{[(2r)-1,2-dihydroxy-2-[(2r,5r,6r)-2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4-dienoic acid

C32H51NO11 (625.3462)


   

(2e,4e,11r)-12-[(4s,4as,6r,8s,8ar)-4-{[(2r)-1,2-dihydroxy-2-[(2r,5r,6r)-2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4-dienoic acid

(2e,4e,11r)-12-[(4s,4as,6r,8s,8ar)-4-{[(2r)-1,2-dihydroxy-2-[(2r,5r,6r)-2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4-dienoic acid

C32H51NO11 (625.3462)


   

12-(4-{[1,2-dihydroxy-2-(2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)-11-hydroxydodeca-2,4-dienoic acid

12-(4-{[1,2-dihydroxy-2-(2-hydroxy-5,6-dimethyl-4-methylideneoxan-2-yl)ethylidene]amino}-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-6-yl)-11-hydroxydodeca-2,4-dienoic acid

C32H51NO11 (625.3462)