Exact Mass: 600.3343424000001

Exact Mass Matches: 600.3343424000001

Found 333 metabolites which its exact mass value is equals to given mass value 600.3343424000001, within given mass tolerance error 0.05 dalton. Try search metabolite list with more accurate mass tolerance error 0.01 dalton.

Phorbol caprate, tiglate

Phorbol 12-tiglate 13-decanoate

C35H52O8 (600.3661992)


D009676 - Noxae > D002273 - Carcinogens > D010703 - Phorbol Esters

   

5-Oxoavermectin 2a aglycone

5-Oxoavermectin 2a aglycone

C34H48O9 (600.3298158)


   

LysoPI(0:0/18:0)

[(2R)-3-hydroxy-2-(octadecanoyloxy)propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

C27H53O12P (600.3274468)


LysoPI(0:0/18:0) is a lysophosphatidylinositol. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic. However, it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylinositols can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPI(0:0/18:0), in particular, consists of one chain of stearic acid at the C-2 position.

   

LysoPI(18:0/0:0)

[(2R)-2-hydroxy-3-(octadecanoyloxy)propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

C27H53O12P (600.3274468)


LysoPI(18:0/0:0) is a lysophosphatidylinositol. The term lysophospholipid (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix lyso- comes from the fact that lysophospholipids were originally found to be hemolytic. However, it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylinositols can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPI(18:0/0:0), in particular, consists of one chain of stearic acid at the C-1 position.

   

Benzoic acid, 4-(4-((2R,5R)-5-((bis(phenylmethyl)amino)carbonyl)-2-heptyl-4-oxo-3-thiazolidinyl)butyl)-, rel-

Benzoic acid, 4-(4-((2R,5R)-5-((bis(phenylmethyl)amino)carbonyl)-2-heptyl-4-oxo-3-thiazolidinyl)butyl)-, rel-

C36H44N2O4S (600.3021624)


   

4-[3-[3-[Bis[4-(2-methylpropyl)phenyl]methylamino]benzoyl]indol-1-yl]butanoic acid

4-{3-[3-({bis[4-(2-methylpropyl)phenyl]methyl}amino)benzoyl]-1H-indol-1-yl}butanoic acid

C40H44N2O3 (600.3351754)


   

Chembl4211493

N-(4,6-Dimethylpyrimidin-2-yl)-4-[2-(4-methoxy-3-methylphenyl)-5-(4-methylpiperazin-1-yl)-4,5,6,7-tetrahydro-1H-indol-1-yl]benzene-1-sulphonamide

C33H40N6O3S (600.2882450000001)


   

Streptolydigin

2-[4-(6-{1,6-dimethyl-8,9-dioxaspiro[bicyclo[3.3.1]nonane-2,2-oxiran]-3-en-7-yl}-1-hydroxy-4-methylhepta-2,4-dien-1-ylidene)-1-(5-hydroxy-6-methyloxan-2-yl)-3,5-dioxopyrrolidin-2-yl]-N-methylpropanimidate

C32H44N2O9 (600.3046654)


   

PA(8:0/20:3(5Z,8Z,11Z)-O(14R,15S))

[(2R)-3-(octanoyloxy)-2-{[(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoyl]oxy}propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:3(5Z,8Z,11Z)-O(14R,15S)) 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(8:0/20:3(5Z,8Z,11Z)-O(14R,15S)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 14,15-epoxyeicosatrienoyl 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(5Z,8Z,11Z)-O(14R,15S)/8:0)

[(2R)-2-(octanoyloxy)-3-{[(5Z,8Z,11Z)-13-(3-pentyloxiran-2-yl)trideca-5,8,11-trienoyl]oxy}propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:3(5Z,8Z,11Z)-O(14R,15S)/8:0) 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(5Z,8Z,11Z)-O(14R,15S)/8:0), in particular, consists of one chain of one 14,15-epoxyeicosatrienoyl at the C-1 position and one chain of octanoyl 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(8:0/20:3(5Z,8Z,14Z)-O(11S,12R))

[(2R)-2-{[(5Z,8Z)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:3(5Z,8Z,14Z)-O(11S,12R)) 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(8:0/20:3(5Z,8Z,14Z)-O(11S,12R)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 11,12-epoxyeicosatrienoyl 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(5Z,8Z,14Z)-O(11S,12R)/8:0)

[(2R)-3-{[(5Z,8Z)-10-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:3(5Z,8Z,14Z)-O(11S,12R)/8:0) 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(5Z,8Z,14Z)-O(11S,12R)/8:0), in particular, consists of one chain of one 11,12-epoxyeicosatrienoyl at the C-1 position and one chain of octanoyl 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(8:0/20:3(5Z,11Z,14Z)-O(8,9))

[(2R)-3-(octanoyloxy)-2-{[(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoyl]oxy}propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:3(5Z,11Z,14Z)-O(8,9)) 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(8:0/20:3(5Z,11Z,14Z)-O(8,9)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 8,9--epoxyeicosatrienoyl 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(5Z,11Z,14Z)-O(8,9)/8:0)

[(2R)-2-(octanoyloxy)-3-{[(5Z)-7-{3-[(2Z,5Z)-undeca-2,5-dien-1-yl]oxiran-2-yl}hept-5-enoyl]oxy}propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:3(5Z,11Z,14Z)-O(8,9)/8:0) 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(5Z,11Z,14Z)-O(8,9)/8:0), in particular, consists of one chain of one 8,9--epoxyeicosatrienoyl at the C-1 position and one chain of octanoyl 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(8:0/20:3(8Z,11Z,14Z)-O(5,6))

[(2R)-3-(octanoyloxy)-2-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:3(8Z,11Z,14Z)-O(5,6)) 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(8:0/20:3(8Z,11Z,14Z)-O(5,6)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 5,6-epoxyeicosatrienoyl 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(8Z,11Z,14Z)-O(5,6)/8:0)

[(2R)-2-(octanoyloxy)-3-[(4-{3-[(2Z,5Z,8Z)-tetradeca-2,5,8-trien-1-yl]oxiran-2-yl}butanoyl)oxy]propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:3(8Z,11Z,14Z)-O(5,6)/8:0) 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(8Z,11Z,14Z)-O(5,6)/8:0), in particular, consists of one chain of one 5,6-epoxyeicosatrienoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(20))

[(2R)-2-{[(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(20)) 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(20)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 20-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(20)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,14Z)-20-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,14Z)-OH(20)/8:0) 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(20:4(5Z,8Z,11Z,14Z)-OH(20)/8:0), in particular, consists of one chain of one 20-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(6E,8Z,11Z,14Z)-OH(5S))

[(2R)-2-{[(5R,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(6E,8Z,11Z,14Z)-OH(5S)) 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(8:0/20:4(6E,8Z,11Z,14Z)-OH(5S)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 5-Hydroxyeicosatetraenoyl 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(20:4(6E,8Z,11Z,14Z)-OH(5S)/8:0)

[(2R)-3-{[(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(6E,8Z,11Z,14Z)-OH(5S)/8:0) 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(20:4(6E,8Z,11Z,14Z)-OH(5S)/8:0), in particular, consists of one chain of one 5-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(19S))

[(2R)-2-{[(5Z,8Z,11Z,14Z,19S)-19-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(19S)) 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(19S)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 19-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(19S)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,14Z,19R)-19-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,14Z)-OH(19S)/8:0) 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(20:4(5Z,8Z,11Z,14Z)-OH(19S)/8:0), in particular, consists of one chain of one 19-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(18R))

[(2R)-2-{[(5Z,8Z,11Z,14Z,18R)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(18R)) 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(18R)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 18-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(18R)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,14Z,18S)-18-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,14Z)-OH(18R)/8:0) 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(20:4(5Z,8Z,11Z,14Z)-OH(18R)/8:0), in particular, consists of one chain of one 18-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(17))

[(2R)-2-{[(5Z,8Z,11Z,14Z)-17-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(17)) 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(17)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 17-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(17)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,14Z)-17-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,14Z)-OH(17)/8:0) 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(20:4(5Z,8Z,11Z,14Z)-OH(17)/8:0), in particular, consists of one chain of one 17-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(16R))

[(2R)-2-{[(5Z,8Z,11Z,14Z,16R)-16-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(16R)) 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(8:0/20:4(5Z,8Z,11Z,14Z)-OH(16R)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 16-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,14Z)-OH(16R)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,14Z,16S)-16-hydroxyicosa-5,8,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,14Z)-OH(16R)/8:0) 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(20:4(5Z,8Z,11Z,14Z)-OH(16R)/8:0), in particular, consists of one chain of one 16-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,11Z,13E)-OH(15S))

[(2R)-2-{[(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,11Z,13E)-OH(15S)) 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(8:0/20:4(5Z,8Z,11Z,13E)-OH(15S)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 15-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,11Z,13E)-OH(15S)/8:0)

[(2R)-3-{[(5Z,8Z,11Z,13E,15R)-15-hydroxyicosa-5,8,11,13-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,11Z,13E)-OH(15S)/8:0) 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(20:4(5Z,8Z,11Z,13E)-OH(15S)/8:0), in particular, consists of one chain of one 15-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,8Z,10E,14Z)-OH(12S))

[(2R)-2-{[(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,8Z,10E,14Z)-OH(12S)) 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(8:0/20:4(5Z,8Z,10E,14Z)-OH(12S)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 12-Hydroxyeicosatetraenoyl 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(20:4(5Z,8Z,10E,14Z)-OH(12S)/8:0)

[(2R)-3-{[(5Z,8Z,10E,12R,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,8Z,10E,14Z)-OH(12S)/8:0) 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(20:4(5Z,8Z,10E,14Z)-OH(12S)/8:0), in particular, consists of one chain of one 12-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5E,8Z,12Z,14Z)-OH(11R))

[(2R)-2-{[(5E,8Z,11R,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5E,8Z,12Z,14Z)-OH(11R)) 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(8:0/20:4(5E,8Z,12Z,14Z)-OH(11R)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 11-Hydroxyeicosatetraenoyl 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(20:4(5E,8Z,12Z,14Z)-OH(11R)/8:0)

[(2R)-3-{[(5E,8Z,11S,12Z,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5E,8Z,12Z,14Z)-OH(11R)/8:0) 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(20:4(5E,8Z,12Z,14Z)-OH(11R)/8:0), in particular, consists of one chain of one 11-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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(8:0/20:4(5Z,7E,11Z,14Z)-OH(9))

[(2R)-2-{[(5E,7Z,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoyl]oxy}-3-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(8:0/20:4(5Z,7E,11Z,14Z)-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(8:0/20:4(5Z,7E,11Z,14Z)-OH(9)), in particular, consists of one chain of one octanoyl at the C-1 position and one chain of 9-Hydroxyeicosatetraenoyl 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(20:4(5Z,7E,11Z,14Z)-OH(9)/8:0)

[(2R)-3-{[(5E,7Z,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoyl]oxy}-2-(octanoyloxy)propoxy]phosphonic acid

C31H53O9P (600.3427018)


PA(20:4(5Z,7E,11Z,14Z)-OH(9)/8:0) 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(20:4(5Z,7E,11Z,14Z)-OH(9)/8:0), in particular, consists of one chain of one 9-Hydroxyeicosatetraenoyl at the C-1 position and one chain of octanoyl 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).

   

Ranaconitine

[(2S,3S,4S,5R,6S,8S,13S,16S,17S)-11-ethyl-3,8,9-trihydroxy-4,6,16-trimethoxy-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-13-yl] 2-acetamidobenzoate

C32H44N2O9 (600.3046654)


   
   
   
   
   
   
   
   
   
   
   

3-O-Geranylforbesione

3-O-Geranylforbesione

C38H48O6 (600.3450708)


   
   
   
   
   
   

12-Ethyl-8-isobutyl-3-vinylbacteriochlorophyllide d

12-Ethyl-8-isobutyl-3-vinylbacteriochlorophyllide d

C36H40MgN4O3+2 (600.295075)


   

7beta,9alpha,14beta-triacetoxy-3beta-benzoyloxy-12beta,15beta-epoxy-11beta-hydroxyjatropha-5E-ene|euphoheliosnoid E

7beta,9alpha,14beta-triacetoxy-3beta-benzoyloxy-12beta,15beta-epoxy-11beta-hydroxyjatropha-5E-ene|euphoheliosnoid E

C33H44O10 (600.2934324)


   
   

milbemycins VM48640

milbemycins VM48640

C35H52O8 (600.3661992)


   

(+)-garcinialiptone

(+)-garcinialiptone

C38H48O6 (600.3450708)


   
   

Phebaloparvilactone

Phebaloparvilactone

C34H48O9 (600.3298158)


   
   

19-dechloro-ansamitocin P-3|19-deschloroansamitocin P-3

19-dechloro-ansamitocin P-3|19-deschloroansamitocin P-3

C32H44N2O9 (600.3046654)


   
   

milbemycins VM44867

milbemycins VM44867

C35H52O8 (600.3661992)


   

3-(4-Hydroxycinnamoyl)-3alpha-3-Hydroxy-7,9(11)-multifloradien-29-oic acid|bryocoumaric acid

3-(4-Hydroxycinnamoyl)-3alpha-3-Hydroxy-7,9(11)-multifloradien-29-oic acid|bryocoumaric acid

C39H52O5 (600.3814542)


   
   

(2R,5S,6S,7R,8S,9S,10S,18R,19R)-18,19-diacetoxy-18,19-epoxy-2-[(2Z,4E)-decadienoyloxy-6,7-dihydroxy]cleroda-3,12(E),14-triene|argutin C

(2R,5S,6S,7R,8S,9S,10S,18R,19R)-18,19-diacetoxy-18,19-epoxy-2-[(2Z,4E)-decadienoyloxy-6,7-dihydroxy]cleroda-3,12(E),14-triene|argutin C

C34H48O9 (600.3298158)


   

bufotalin 3-hemisuberate|Korksaeure-mono-<3>bufotalylester|Korksaeure-mono-[3]bufotalylester

bufotalin 3-hemisuberate|Korksaeure-mono-<3>bufotalylester|Korksaeure-mono-[3]bufotalylester

C34H48O9 (600.3298158)


   
   

6-hydroxy-hardwickiic acid 2-beta-D-glucopyranosylbenzyl ester

6-hydroxy-hardwickiic acid 2-beta-D-glucopyranosylbenzyl ester

C33H44O10 (600.2934324)


   
   
   

12xi-acetoxy-11beta-hydroxypetuniasterone D 7-acetate

12xi-acetoxy-11beta-hydroxypetuniasterone D 7-acetate

C34H48O9 (600.3298158)


   

isophytolaccinic acid A

isophytolaccinic acid A

C35H52O8 (600.3661992)


   
   

milbemycin alpha22

milbemycin alpha22

C34H48O9 (600.3298158)


   
   

(2R,5S,6S,7R,8S,9S,10S,18R,19R)-18,19-diacetoxy-18,19-epoxy-2,7-dihydroxy-6-[(2Z,4E)-decadienoyloxy]cleroda-3,12(E),14-triene|argutin D

(2R,5S,6S,7R,8S,9S,10S,18R,19R)-18,19-diacetoxy-18,19-epoxy-2,7-dihydroxy-6-[(2Z,4E)-decadienoyloxy]cleroda-3,12(E),14-triene|argutin D

C34H48O9 (600.3298158)


   

oxy-guttiferone M

oxy-guttiferone M

C38H48O6 (600.3450708)


   

oxy-guttiferone K

oxy-guttiferone K

C38H48O6 (600.3450708)


   

polypodin B-22-O-benzoate|polypodine B-22-O-benzoate

polypodin B-22-O-benzoate|polypodine B-22-O-benzoate

C34H48O9 (600.3298158)


   
   

17-hydroxy-euphornin|7beta,9alpha,14beta-triacetoxy-3beta-benzoyloxy-15beta,17-dihydroxyjatropha-5E,11E-diene

17-hydroxy-euphornin|7beta,9alpha,14beta-triacetoxy-3beta-benzoyloxy-15beta,17-dihydroxyjatropha-5E,11E-diene

C33H44O10 (600.2934324)


   
   

(20R,22S)-1-oxo-witha-2,5,24-trienolide-20-beta-ol 20-beta-D-glucopyranoside|glucosomniferanolide

(20R,22S)-1-oxo-witha-2,5,24-trienolide-20-beta-ol 20-beta-D-glucopyranoside|glucosomniferanolide

C34H48O9 (600.3298158)


   
   
   
   

11,25-dideacetyl trichostemonate

11,25-dideacetyl trichostemonate

C34H48O9 (600.3298158)


   
   
   

rel-(1R,3S,5R,7S,8R)-1-(3,4-dihydroxybenzoyl)-6,6-dimethyl-5-(3-methylbut-2-en-1-yl)-3-[5-methyl-2-(1-methylethenyl)hex-4-en-1-yl]-8-(2-methylprop-1-en-1-yl)tricyclo[3,3,1,13,7]decane-2,4,9-trione

rel-(1R,3S,5R,7S,8R)-1-(3,4-dihydroxybenzoyl)-6,6-dimethyl-5-(3-methylbut-2-en-1-yl)-3-[5-methyl-2-(1-methylethenyl)hex-4-en-1-yl]-8-(2-methylprop-1-en-1-yl)tricyclo[3,3,1,13,7]decane-2,4,9-trione

C38H48O6 (600.3450708)


   

21-(E)-coumaroyloxy-5alpha-cycloart-24-ene-3,23-dione

21-(E)-coumaroyloxy-5alpha-cycloart-24-ene-3,23-dione

C39H52O5 (600.3814542)


   
   

7,8-didehydro-25-anhydrocimigenol-3-beta-D-xylopyranoside

7,8-didehydro-25-anhydrocimigenol-3-beta-D-xylopyranoside

C35H52O8 (600.3661992)


   

Cimicifugoside H-1

Cimicifugoside H-1

C35H52O8 (600.3661992)


   
   

4alpha-acetyl-2beta-angeloyl-5alpha,8-diisobutyryl-1beta,3alpha,10,11-tetrahydroxybisabolene

4alpha-acetyl-2beta-angeloyl-5alpha,8-diisobutyryl-1beta,3alpha,10,11-tetrahydroxybisabolene

C30H48O12 (600.3145608)


   
   

4alpha-acetyl-2beta-angeloyl-5alpha,10-diisobutyryl-1beta,3alpha,8,11-tetrahydroxybisabolene

4alpha-acetyl-2beta-angeloyl-5alpha,10-diisobutyryl-1beta,3alpha,8,11-tetrahydroxybisabolene

C30H48O12 (600.3145608)


   

klysimplexin sulfoxide C

klysimplexin sulfoxide C

C30H48O10S (600.2968028)


   

16alpha,25-Diacetoxy-2beta,20-dihydroxy-10alpha-cucurbita-5,23t-dien-3,11,22-trion|16alpha,25-diacetoxy-2beta,20-dihydroxy-10alpha-cucurbita-5,23t-diene-3,11,22-trione|Fabacein

16alpha,25-Diacetoxy-2beta,20-dihydroxy-10alpha-cucurbita-5,23t-dien-3,11,22-trion|16alpha,25-diacetoxy-2beta,20-dihydroxy-10alpha-cucurbita-5,23t-diene-3,11,22-trione|Fabacein

C34H48O9 (600.3298158)


   

klysimplexin sulfoxide B

klysimplexin sulfoxide B

C31H52O9S (600.3331862)


   
   

6-acetoxytropan-3-yl tropan-3-yl truxillate

6-acetoxytropan-3-yl tropan-3-yl truxillate

C36H44N2O6 (600.3199204)


   
   

oxy-guttiferone K2

oxy-guttiferone K2

C38H48O6 (600.3450708)


   
   

2,16-Di-O-acetylcucurbitacin D|2,16-Di-O-acetylcucurbitacin R|2beta,16alpha-Diacetoxy-20,25-dihydroxy-10alpha-cucurbita-5,23t-dien-3,11,22-trion|2beta,16alpha-diacetoxy-20,25-dihydroxy-10alpha-cucurbita-5,23t-diene-3,11,22-trione

2,16-Di-O-acetylcucurbitacin D|2,16-Di-O-acetylcucurbitacin R|2beta,16alpha-Diacetoxy-20,25-dihydroxy-10alpha-cucurbita-5,23t-dien-3,11,22-trion|2beta,16alpha-diacetoxy-20,25-dihydroxy-10alpha-cucurbita-5,23t-diene-3,11,22-trione

C34H48O9 (600.3298158)


   
   
   
   
   
   
   
   

Phosphatidylinositol lyso 18:0

Phosphatidylinositol lyso 18:0

C27H53O12P (600.3274468)


   
   

1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone

NCGC00180673-03!1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone

C27H48N6O9 (600.3482597999999)


   

Desferrioxamine E

Desferrioxamine E

C27H48N6O9 (600.3482597999999)


A cyclic hydroxamic acid siderophore that is produced by several bacterial species and exhibits antitumour activity.

   

[2-hydroxy-3-[hydroxy-[2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] octadecanoate

[2-hydroxy-3-[hydroxy-[2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphoryl]oxypropyl] octadecanoate

C27H53O12P (600.3274468)


   

1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone [IIN-based on: CCMSLIB00000846839]

NCGC00180673-03!1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone [IIN-based on: CCMSLIB00000846839]

C27H48N6O9 (600.3482597999999)


   

1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone [IIN-based: Match]

NCGC00180673-03!1,12,23-trihydroxy-1,6,12,17,23,28-hexazacyclotritriacontane-2,5,13,16,24,27-hexone [IIN-based: Match]

C27H48N6O9 (600.3482597999999)


   

Ile Pro Trp Trp

(2S)-2-[(2S)-2-{[(2S)-1-[(2S,3S)-2-amino-3-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Ile Trp Pro Trp

(2S)-2-{[(2S)-1-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Ile Trp Trp Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S,3S)-2-amino-3-methylpentanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Lys Lys Tyr Tyr

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2,6-diaminohexanamido]hexanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanoic acid

C30H44N6O7 (600.3271314)


   

Lys Gln Tyr Tyr

(2S)-2-[(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2,6-diaminohexanamido]butanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Lys Tyr Lys Tyr

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(4-hydroxyphenyl)propanamido]hexanamido]-3-(4-hydroxyphenyl)propanoic acid

C30H44N6O7 (600.3271314)


   

Lys Tyr Gln Tyr

(2S)-2-[(2S)-4-carbamoyl-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(4-hydroxyphenyl)propanamido]butanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Lys Tyr Tyr Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]hexanoic acid

C30H44N6O7 (600.3271314)


   

Lys Tyr Tyr Gln

(2S)-4-carbamoyl-2-[(2S)-2-[(2S)-2-[(2S)-2,6-diaminohexanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]butanoic acid

C29H40N6O8 (600.290748)


   

Leu Pro Trp Trp

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Leu Trp Pro Trp

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Leu Trp Trp Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-methylpentanamido]-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Asn Arg Arg Arg

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid

C22H44N14O6 (600.3568084000001)


   

Pro Ile Trp Trp

(2S)-3-(1H-indol-3-yl)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S,3S)-3-methyl-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]propanamido]propanoic acid

C33H40N6O5 (600.306003)


   

Pro Leu Trp Trp

(2S)-3-(1H-indol-3-yl)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-4-methyl-2-[(2S)-pyrrolidin-2-ylformamido]pentanamido]propanamido]propanoic acid

C33H40N6O5 (600.306003)


   

Pro Trp Ile Trp

(2S)-3-(1H-indol-3-yl)-2-[(2S,3S)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]-3-methylpentanamido]propanoic acid

C33H40N6O5 (600.306003)


   

Pro Trp Leu Trp

(2S)-3-(1H-indol-3-yl)-2-[(2S)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]-4-methylpentanamido]propanoic acid

C33H40N6O5 (600.306003)


   

Pro Trp Trp Ile

(2S,3S)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]propanamido]-3-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Pro Trp Trp Leu

(2S)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-3-(1H-indol-3-yl)-2-[(2S)-pyrrolidin-2-ylformamido]propanamido]propanamido]-4-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Gln Lys Tyr Tyr

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-4-carbamoylbutanamido]hexanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Gln Tyr Lys Tyr

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]hexanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Gln Tyr Tyr Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]hexanoic acid

C29H40N6O8 (600.290748)


   

Arg Asn Arg Arg

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-3-carbamoylpropanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanoic acid

C22H44N14O6 (600.3568084000001)


   

Arg Arg Asn Arg

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-carbamoylpropanamido]-5-carbamimidamidopentanoic acid

C22H44N14O6 (600.3568084000001)


   

Arg Arg Arg Asn

(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-5-carbamimidamidopentanamido]-3-carbamoylpropanoic acid

C22H44N14O6 (600.3568084000001)


   

Trp Ile Pro Trp

(2S)-2-{[(2S)-1-[(2S,3S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Trp Ile Trp Pro

(2S)-1-[(2S)-2-[(2S,3S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-methylpentanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Trp Leu Pro Trp

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-methylpentanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Trp Leu Trp Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-4-methylpentanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Trp Pro Ile Trp

(2S)-2-[(2S,3S)-2-{[(2S)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanamido]-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Trp Pro Leu Trp

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanamido]-3-(1H-indol-3-yl)propanoic acid

C33H40N6O5 (600.306003)


   

Trp Pro Trp Ile

(2S,3S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-3-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Trp Pro Trp Leu

(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-(1H-indol-3-yl)propanamido]-4-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Trp Trp Ile Pro

(2S)-1-[(2S,3S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-3-methylpentanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Trp Trp Leu Pro

(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanamido]-4-methylpentanoyl]pyrrolidine-2-carboxylic acid

C33H40N6O5 (600.306003)


   

Trp Trp Pro Ile

(2S,3S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-3-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Trp Trp Pro Leu

(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanamido]-3-(1H-indol-3-yl)propanoyl]pyrrolidin-2-yl]formamido}-4-methylpentanoic acid

C33H40N6O5 (600.306003)


   

Tyr Lys Lys Tyr

(2S)-2-[(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]hexanamido]hexanamido]-3-(4-hydroxyphenyl)propanoic acid

C30H44N6O7 (600.3271314)


   

Tyr Lys Gln Tyr

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]hexanamido]-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Tyr Lys Tyr Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]hexanamido]-3-(4-hydroxyphenyl)propanamido]hexanoic acid

C30H44N6O7 (600.3271314)


   

Tyr Lys Tyr Gln

(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]hexanamido]-3-(4-hydroxyphenyl)propanamido]-4-carbamoylbutanoic acid

C29H40N6O8 (600.290748)


   

Tyr Gln Lys Tyr

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-carbamoylbutanamido]hexanamido]-3-(4-hydroxyphenyl)propanoic acid

C29H40N6O8 (600.290748)


   

Tyr Gln Tyr Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-4-carbamoylbutanamido]-3-(4-hydroxyphenyl)propanamido]hexanoic acid

C29H40N6O8 (600.290748)


   

Tyr Tyr Lys Lys

(2S)-6-amino-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]hexanamido]hexanoic acid

C30H44N6O7 (600.3271314)


   

Tyr Tyr Lys Gln

(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]hexanamido]-4-carbamoylbutanoic acid

C29H40N6O8 (600.290748)


   

Tyr Tyr Gln Lys

(2S)-6-amino-2-[(2S)-2-[(2S)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-3-(4-hydroxyphenyl)propanamido]-4-carbamoylbutanamido]hexanoic acid

C29H40N6O8 (600.290748)


   

QHLFG

Gln His Leu Phe Gly

C28H40N8O7 (600.3019810000001)


   

LAREL

Leu Ala Arg Glu Leu

C26H48N8O8 (600.3594928)


   

RNLAK

Arg-Asn-Leu-Ala-Lys

C25H48N10O7 (600.3707258)


   

KRNLA

Lys-Arg-Asn-Leu-Ala

C25H48N10O7 (600.3707258)


   

PI(18:0/0:0)

1-octadecanoyl-sn-glycero-3-phospho-(1-myo-inositol)

C27H53O12P (600.3274468)


   

LPI 18:0

1-octadecanoyl-sn-glycero-3-phospho-(1-myo-inositol)

C27H53O12P (600.3274468)


   

Glc-GP 18:0

1-octadecanoyl-sn-glycero-3-phospho-(1-beta-D-glucose)

C27H53O12P (600.3274468)


   

Streptolydigin

Streptolydigin

C32H44N2O9 (600.3046654)


A monocarboxylic acid amide that is a broad-spectrum antibiotic produced by Streptomyces lydicus. D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents

   
   

Bradykinin (2-7) acetate salt

Bradykinin (2-7) acetate salt

C29H40N6O8 (600.290748)


   

BETA-D-GALACTOSE PENTAPIVALATE

BETA-D-GALACTOSE PENTAPIVALATE

C31H52O11 (600.3509442)


   

1,2,3,4,6-Penta-O-pivaloyl-D-mannopyranose

1,2,3,4,6-Penta-O-pivaloyl-D-mannopyranose

C31H52O11 (600.3509442)


   

4-[3-[3-[Bis[4-(2-methylpropyl)phenyl]methylamino]benzoyl]indol-1-yl]butanoic acid

4-[3-[3-[Bis[4-(2-methylpropyl)phenyl]methylamino]benzoyl]indol-1-yl]butanoic acid

C40H44N2O3 (600.3351754)


D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D065088 - Steroid Synthesis Inhibitors D004791 - Enzyme Inhibitors > D065088 - Steroid Synthesis Inhibitors > D058891 - 5-alpha Reductase Inhibitors

   

3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid

3-beta-O-(E)-coumaroyl-D:C-friedooleana-7,9(11)-dien-29-oic acid

C39H52O5 (600.3814542)


A pentacyclic triterpenoid that is the cinnamate ester obtained by the formal condensation of trans-4-coumaric acid with D:C-friedoolean-7,9(11)-dien-3beta-ol-29-oic acid. It is isolated from the stems of Lagenaria siceraria and exhibits cytotoxic activity against human hepatoma SK-Hep 1 cells.

   

Ethyl (4R)-4-{[(2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-1,2-oxazol-3-yl)carbonyl]amino}-4-oxoheptanoyl]amino}-5-[(3S)-2-oxo-3-pyrrolidinyl]pentanoate

Ethyl (4R)-4-{[(2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-1,2-oxazol-3-yl)carbonyl]amino}-4-oxoheptanoyl]amino}-5-[(3S)-2-oxo-3-pyrrolidinyl]pentanoate

C31H41FN4O7 (600.2959128)


   

1-stearoyl-sn-glycero-3-phospho-1D-myo-inositol

1-stearoyl-sn-glycero-3-phospho-1D-myo-inositol

C27H53O12P (600.3274468)


A 1-acyl-sn-glycero-3-phospho-1D-myo-inositol in which the 1-acyl group is specified as stearoyl.

   
   

2-Stearoylglycerophosphoinositol

2-Stearoylglycerophosphoinositol

C27H53O12P (600.3274468)


   

2-[(4E)-4-[(2E,4E)-6-(1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2-oxirane]-3-yl)-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-(5-hydroxy-6-methyloxan-2-yl)-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide

2-[(4E)-4-[(2E,4E)-6-(1,4-dimethylspiro[2,9-dioxabicyclo[3.3.1]non-6-ene-8,2-oxirane]-3-yl)-1-hydroxy-4-methylhepta-2,4-dienylidene]-1-(5-hydroxy-6-methyloxan-2-yl)-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide

C32H44N2O9 (600.3046654)


   

PA(8:0/20:4(6E,8Z,11Z,14Z)-OH(5S))

PA(8:0/20:4(6E,8Z,11Z,14Z)-OH(5S))

C31H53O9P (600.3427018)


   

PA(20:4(6E,8Z,11Z,14Z)-OH(5S)/8:0)

PA(20:4(6E,8Z,11Z,14Z)-OH(5S)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,7E,11Z,14Z)-OH(9))

PA(8:0/20:4(5Z,7E,11Z,14Z)-OH(9))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,7E,11Z,14Z)-OH(9)/8:0)

PA(20:4(5Z,7E,11Z,14Z)-OH(9)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:3(5Z,8Z,11Z)-O(14R,15S))

PA(8:0/20:3(5Z,8Z,11Z)-O(14R,15S))

C31H53O9P (600.3427018)


   

PA(20:3(5Z,8Z,11Z)-O(14R,15S)/8:0)

PA(20:3(5Z,8Z,11Z)-O(14R,15S)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:3(5Z,8Z,14Z)-O(11S,12R))

PA(8:0/20:3(5Z,8Z,14Z)-O(11S,12R))

C31H53O9P (600.3427018)


   

PA(20:3(5Z,8Z,14Z)-O(11S,12R)/8:0)

PA(20:3(5Z,8Z,14Z)-O(11S,12R)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:3(5Z,11Z,14Z)-O(8,9))

PA(8:0/20:3(5Z,11Z,14Z)-O(8,9))

C31H53O9P (600.3427018)


   

PA(20:3(5Z,11Z,14Z)-O(8,9)/8:0)

PA(20:3(5Z,11Z,14Z)-O(8,9)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:3(8Z,11Z,14Z)-O(5,6))

PA(8:0/20:3(8Z,11Z,14Z)-O(5,6))

C31H53O9P (600.3427018)


   

PA(20:3(8Z,11Z,14Z)-O(5,6)/8:0)

PA(20:3(8Z,11Z,14Z)-O(5,6)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(20))

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(20))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,14Z)-OH(20)/8:0)

PA(20:4(5Z,8Z,11Z,14Z)-OH(20)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(19S))

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(19S))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,14Z)-OH(19S)/8:0)

PA(20:4(5Z,8Z,11Z,14Z)-OH(19S)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(18R))

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(18R))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,14Z)-OH(18R)/8:0)

PA(20:4(5Z,8Z,11Z,14Z)-OH(18R)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(17))

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(17))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,14Z)-OH(17)/8:0)

PA(20:4(5Z,8Z,11Z,14Z)-OH(17)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(16R))

PA(8:0/20:4(5Z,8Z,11Z,14Z)-OH(16R))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,14Z)-OH(16R)/8:0)

PA(20:4(5Z,8Z,11Z,14Z)-OH(16R)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,11Z,13E)-OH(15S))

PA(8:0/20:4(5Z,8Z,11Z,13E)-OH(15S))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,11Z,13E)-OH(15S)/8:0)

PA(20:4(5Z,8Z,11Z,13E)-OH(15S)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5Z,8Z,10E,14Z)-OH(12S))

PA(8:0/20:4(5Z,8Z,10E,14Z)-OH(12S))

C31H53O9P (600.3427018)


   

PA(20:4(5Z,8Z,10E,14Z)-OH(12S)/8:0)

PA(20:4(5Z,8Z,10E,14Z)-OH(12S)/8:0)

C31H53O9P (600.3427018)


   

PA(8:0/20:4(5E,8Z,12Z,14Z)-OH(11R))

PA(8:0/20:4(5E,8Z,12Z,14Z)-OH(11R))

C31H53O9P (600.3427018)


   

PA(20:4(5E,8Z,12Z,14Z)-OH(11R)/8:0)

PA(20:4(5E,8Z,12Z,14Z)-OH(11R)/8:0)

C31H53O9P (600.3427018)


   

2-[[(2R)-3-acetyloxy-2-[(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,14Z,16E,18R)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,11Z,13E,17Z)-16-hydroxyicosa-5,8,11,13,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(5Z,8Z,10E,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-3-acetyloxy-2-[(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-3-acetyloxy-2-[(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   

2-[[(2R)-2-acetyloxy-3-[(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[(2R)-2-acetyloxy-3-[(6E,8Z,11Z,14Z,17Z)-5-hydroxyicosa-6,8,11,14,17-pentaenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C30H51NO9P+ (600.3301266)


   
   
   

Benzyl ((2S)-3-(tert-butoxy)-1-(((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)amino)-1-oxobutan-2-yl)carbamate

Benzyl ((2S)-3-(tert-butoxy)-1-(((S)-3-cyclohexyl-1-oxo-1-(((S)-1-oxo-3-((S)-2-oxopyrrolidin-3-yl)propan-2-yl)amino)propan-2-yl)amino)-1-oxobutan-2-yl)carbamate

C32H48N4O7 (600.3522817999999)


   

Argutin C

Argutin C

C34H48O9 (600.3298158)


A natural product found in Casearia arguta.

   

Cbz-1Nal-Leu-Ala((S)-2-oxopyrrolidin-3-yl)-al

Cbz-1Nal-Leu-Ala((S)-2-oxopyrrolidin-3-yl)-al

C34H40N4O6 (600.29477)


   

Argutin D

Argutin D

C34H48O9 (600.3298158)


A natural product found in Casearia arguta.

   

(2R)-2-hydroxy-3-[(hydroxy{[(1S,2R,3S,4S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphoryl)oxy]propyl stearate

(2R)-2-hydroxy-3-[(hydroxy{[(1S,2R,3S,4S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl]oxy}phosphoryl)oxy]propyl stearate

C27H53O12P (600.3274468)


   

5-Oxoavermectin2a aglycone

5-Oxoavermectin 2a aglycone

C34H48O9 (600.3298158)


   

[2-Hydroxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropyl] octadecanoate

[2-Hydroxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropyl] octadecanoate

C27H53O12P (600.3274468)


   
   

2,3-dihydroxypropyl [3-[(11Z,14Z,17Z,20Z,23Z)-hexacosa-11,14,17,20,23-pentaenoxy]-2-hydroxypropyl] hydrogen phosphate

2,3-dihydroxypropyl [3-[(11Z,14Z,17Z,20Z,23Z)-hexacosa-11,14,17,20,23-pentaenoxy]-2-hydroxypropyl] hydrogen phosphate

C32H57O8P (600.3790852)


   
   
   
   
   
   
   
   
   
   

[1-[(2-hexanoyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate

[1-[(2-hexanoyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (3Z,6Z,9Z,12Z,15Z)-octadeca-3,6,9,12,15-pentaenoate

C30H49O10P (600.3063184)


   

[1-[(2-butanoyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

[1-[(2-butanoyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

C30H49O10P (600.3063184)


   

[1-[(2-acetyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

[1-[(2-acetyloxy-3-hydroxypropoxy)-hydroxyphosphoryl]oxy-3-hydroxypropan-2-yl] (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

C30H49O10P (600.3063184)


   

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-octanoyloxypropan-2-yl] nonanoate

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-octanoyloxypropan-2-yl] nonanoate

C26H49O13P (600.2910634)


   

(1-nonanoyloxy-3-phosphonooxypropan-2-yl) (11Z,14Z,17Z)-icosa-11,14,17-trienoate

(1-nonanoyloxy-3-phosphonooxypropan-2-yl) (11Z,14Z,17Z)-icosa-11,14,17-trienoate

C32H57O8P (600.3790852)


   

[1-Hexanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] undecanoate

[1-Hexanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] undecanoate

C26H49O13P (600.2910634)


   

[1-butanoyloxy-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxypropan-2-yl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

[1-butanoyloxy-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxypropan-2-yl] (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate

C30H49O10P (600.3063184)


   

[1-Heptanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] decanoate

[1-Heptanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] decanoate

C26H49O13P (600.2910634)


   

(1-heptanoyloxy-3-phosphonooxypropan-2-yl) (10Z,13Z,16Z)-docosa-10,13,16-trienoate

(1-heptanoyloxy-3-phosphonooxypropan-2-yl) (10Z,13Z,16Z)-docosa-10,13,16-trienoate

C32H57O8P (600.3790852)


   

[1-acetyloxy-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxypropan-2-yl] (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

[1-acetyloxy-3-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxypropan-2-yl] (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate

C30H49O10P (600.3063184)


   

[1-Butanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] tridecanoate

[1-Butanoyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] tridecanoate

C26H49O13P (600.2910634)


   

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

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

C30H49O10P (600.3063184)


   

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-propanoyloxypropan-2-yl] tetradecanoate

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-propanoyloxypropan-2-yl] tetradecanoate

C26H49O13P (600.2910634)


   

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-pentanoyloxypropan-2-yl] dodecanoate

[1-[Hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxy-3-pentanoyloxypropan-2-yl] dodecanoate

C26H49O13P (600.2910634)


   

[1-phosphonooxy-3-[(Z)-tridec-9-enoyl]oxypropan-2-yl] (9Z,12Z)-hexadeca-9,12-dienoate

[1-phosphonooxy-3-[(Z)-tridec-9-enoyl]oxypropan-2-yl] (9Z,12Z)-hexadeca-9,12-dienoate

C32H57O8P (600.3790852)


   

(1-phosphonooxy-3-tridecanoyloxypropan-2-yl) (7Z,10Z,13Z)-hexadeca-7,10,13-trienoate

(1-phosphonooxy-3-tridecanoyloxypropan-2-yl) (7Z,10Z,13Z)-hexadeca-7,10,13-trienoate

C32H57O8P (600.3790852)


   

(1-phosphonooxy-3-undecanoyloxypropan-2-yl) (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

(1-phosphonooxy-3-undecanoyloxypropan-2-yl) (9Z,12Z,15Z)-octadeca-9,12,15-trienoate

C32H57O8P (600.3790852)


   

[1-Acetyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] pentadecanoate

[1-Acetyloxy-3-[hydroxy-(2,3,4,5,6-pentahydroxycyclohexyl)oxyphosphoryl]oxypropan-2-yl] pentadecanoate

C26H49O13P (600.2910634)


   

(1-phosphonooxy-3-tridecanoyloxypropan-2-yl) (9E,11E,13E)-hexadeca-9,11,13-trienoate

(1-phosphonooxy-3-tridecanoyloxypropan-2-yl) (9E,11E,13E)-hexadeca-9,11,13-trienoate

C32H57O8P (600.3790852)


   

[(2R)-1-phosphonooxy-3-undecanoyloxypropan-2-yl] (6E,9E,12E)-octadeca-6,9,12-trienoate

[(2R)-1-phosphonooxy-3-undecanoyloxypropan-2-yl] (6E,9E,12E)-octadeca-6,9,12-trienoate

C32H57O8P (600.3790852)


   

[1-phosphonooxy-3-[(E)-tridec-8-enoyl]oxypropan-2-yl] (4E,7E)-hexadeca-4,7-dienoate

[1-phosphonooxy-3-[(E)-tridec-8-enoyl]oxypropan-2-yl] (4E,7E)-hexadeca-4,7-dienoate

C32H57O8P (600.3790852)


   

[(2R)-3-phosphonooxy-2-undecanoyloxypropyl] (6E,9E,12E)-octadeca-6,9,12-trienoate

[(2R)-3-phosphonooxy-2-undecanoyloxypropyl] (6E,9E,12E)-octadeca-6,9,12-trienoate

C32H57O8P (600.3790852)


   

[(2R)-3-phosphonooxy-2-undecanoyloxypropyl] (9E,12E,15E)-octadeca-9,12,15-trienoate

[(2R)-3-phosphonooxy-2-undecanoyloxypropyl] (9E,12E,15E)-octadeca-9,12,15-trienoate

C32H57O8P (600.3790852)


   

[(2R)-1-phosphonooxy-3-undecanoyloxypropan-2-yl] (9E,12E,15E)-octadeca-9,12,15-trienoate

[(2R)-1-phosphonooxy-3-undecanoyloxypropan-2-yl] (9E,12E,15E)-octadeca-9,12,15-trienoate

C32H57O8P (600.3790852)


   

2-[hydroxy-[2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl]oxy-3-propanoyloxypropoxy]phosphoryl]oxyethyl-trimethylazanium

2-[hydroxy-[2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl]oxy-3-propanoyloxypropoxy]phosphoryl]oxyethyl-trimethylazanium

C31H55NO8P+ (600.36651)


   

2-[hydroxy-[2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyl]oxy-3-pentanoyloxypropoxy]phosphoryl]oxyethyl-trimethylazanium

2-[hydroxy-[2-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyl]oxy-3-pentanoyloxypropoxy]phosphoryl]oxyethyl-trimethylazanium

C31H55NO8P+ (600.36651)


   

2-[[3-heptanoyloxy-2-[(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

2-[[3-heptanoyloxy-2-[(4Z,7Z,10Z,13Z)-hexadeca-4,7,10,13-tetraenoyl]oxypropoxy]-hydroxyphosphoryl]oxyethyl-trimethylazanium

C31H55NO8P+ (600.36651)


   

Casearupestrin B, (rel)-

Casearupestrin B, (rel)-

C34H48O9 (600.3298158)


A natural product found in Casearia rupestris.

   

Casearupestrin A, (rel)-

Casearupestrin A, (rel)-

C34H48O9 (600.3298158)


A natural product found in Casearia rupestris.

   

1-octadecanoyl-sn-glycero-3-phospho-(1-myo-inositol)

1-octadecanoyl-sn-glycero-3-phospho-(1-myo-inositol)

C27H53O12P (600.3274468)


   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   

6-O-(1-O-Stearoyl-sn-glycero-3-phosphono)-1D-myo-inositol

6-O-(1-O-Stearoyl-sn-glycero-3-phosphono)-1D-myo-inositol

C27H53O12P (600.3274468)


   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   
   

Ac-Arg-Gly-Lys(Ac)-AMC

Ac-Arg-Gly-Lys(Ac)-AMC

C28H40N8O7 (600.3019810000001)


Ac-Arg-Gly-Lys(Ac)-AMC is a substrate for HDAC[1].