PA(20:0/18:1(12Z)-2OH(9,10))

[(2R)-2-{[(9S,10S,12Z)-9,10-dihydroxyoctadec-12-enoyl]oxy}-3-(icosanoyloxy)propoxy]phosphonic acid

Formula: C41H79O10P (762.5411)
Chinese Name:
BioDeep ID: BioDeep_00000189666 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC[C@H](O)[C@@H](O)C\C=C/CCCCC



Found 17 Sample Hits

m/z Adducts Species Organ Scanning Sample
763.5401 [M+H]+
PPM:10.8
Mus musculus Lung MALDI (DHB)
image2 - MTBLS2075
Resolution: 40μm, 550x256

Description

Supplementary Figure S6. Ion distribution images for (a) [PC36:4+Na]+ (m/z 804.5514) and (b) [PC38:6+Na]+ (m/z 828.5515) obtained from mouse lung tissue collected 6 h after administration of D9- choline and U13C-DPPC–containing CHF5633. Parts-per-million (ppm) mass errors are indicated in parentheses. (c) Magnification of the boxed region in (a) with selected bronchiolar regions outlined in white boxes. (d) The corresponding H&E-stained tissue section with the same selected bronchiolar regions outlined in black boxes. These data demonstrate the co-localisation of the polyunsaturated lipids PC36:4 and PC38:6 with the bronchiolar regions of the lung. All MSI images were visualised using total ion current normalisation and hotspot removal (high quantile = 99%).

780.5661 [M+NH4]+
PPM:11.3
Macropus giganteus Brain MALDI (BPYN)
170321_kangaroobrain-dan3-pos_maxof50.0_med1 - 170321_kangaroobrain-dan3-pos_maxof50.0_med1
Resolution: 50μm, 81x50

Description

Sample information Organism: Macropus giganteus (kangaroo) Organism part: Brain Condition: Wildtype Sample growth conditions: Wild

763.5497 [M+H]+
PPM:1.8
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

780.5768 [M+NH4]+
PPM:2.5
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).

780.5716 [M+NH4]+
PPM:4.2
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

763.5496 [M+H]+
PPM:1.7
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

780.5802 [M+NH4]+
PPM:6.8
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

763.5493 [M+H]+
PPM:1.3
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

780.5798 [M+NH4]+
PPM:6.3
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

763.5494 [M+H]+
PPM:1.4
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

780.5822 [M+NH4]+
PPM:9.4
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

763.5475 [M+H]+
PPM:1.1
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

780.5813 [M+NH4]+
PPM:8.2
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

780.5763 [M+NH4]+
PPM:1.8
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

780.5809 [M+NH4]+
PPM:7.7
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

780.5794 [M+NH4]+
PPM:5.8
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

780.5794 [M+NH4]+
PPM:5.8
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


PA(20:0/18:1(12Z)-2OH(9,10)) 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(20:0/18:1(12Z)-2OH(9,10)), in particular, consists of one chain of one eicosanoyl at the C-1 position and one chain of 9,10-hydroxy-octadecenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PAs can be synthesized via three different routes. In one route, the oxidized PA is synthetized de novo following the same mechanisms as for PAs but incorporating oxidized acyl chains (PMID: 33329396). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396). The third pathway results from the oxidation of the acyl chain while still attached to the PA backbone, mainly through the action of LOX (PMID: 33329396).