PA(20:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4))

[(2R)-2-{[(5Z,7Z,10Z,13Z,16Z,19Z)-4-hydroxydocosa-5,7,10,13,16,19-hexaenoyl]oxy}-3-(icosanoyloxy)propoxy]phosphonic acid

Formula: C45H77O9P (792.5305)
Chinese Name:
BioDeep ID: BioDeep_00000189688 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCC(O)\C=C/C=C\C\C=C/C\C=C/C\C=C/C\C=C/CC



Found 26 Sample Hits

m/z Adducts Species Organ Scanning Sample
757.5154 [M+H-2H2O]+
PPM:1.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

793.5243 [M+H]+
PPM:17
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

793.5359 [M+H]+
PPM:2.4
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

793.5351 [M+H]+
PPM:3.4
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

793.5369 [M+H]+
PPM:1.1
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

793.5504 [M+H]+
PPM:15.9
Homo sapiens colorectal adenocarcinoma DESI ()
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415
Resolution: 17μm, 137x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

793.5504 [M+H]+
PPM:15.9
Homo sapiens colorectal adenocarcinoma DESI ()
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415
Resolution: 17μm, 147x131

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

793.5348 [M+H]+
PPM:3.7
Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

Description

The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024).

793.5487 [M+H]+
PPM:13.8
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

793.5352 [M+H]+
PPM:3.2
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

793.5257 [M+H]+
PPM:15.2
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

793.536 [M+H]+
PPM:2.2
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

793.5356 [M+H]+
PPM:2.7
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

793.5349 [M+H]+
PPM:3.6
Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

793.5353 [M+H]+
PPM:3.1
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

793.5358 [M+H]+
PPM:2.5
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

793.5356 [M+H]+
PPM:2.7
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

793.5251 [M+H]+
PPM:16
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

793.5322 [M+H]+
PPM:7
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

793.5371 [M+H]+
PPM:0.8
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

793.535 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

793.535 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

793.5345 [M+H]+
PPM:4.1
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

793.5352 [M+H]+
PPM:3.2
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

793.5343 [M+H]+
PPM:4.4
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

793.5348 [M+H]+
PPM:3.7
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


PA(20:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)) is an oxidized phosphatidic acid (PA). Oxidized phosphatidic acids are glycerophospholipids in which a phosphate moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidic acids belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396). As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PA(20:0/22:6(5Z,7Z,10Z,13Z,16Z,19Z)-OH(4)), in particular, consists of one chain of one eicosanoyl at the C-1 position and one chain of 4-hydroxy-docosahexaenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized 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).