PE(18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15))

(2-aminoethoxy)[(2R)-3-(octadecanoyloxy)-2-{[(5R,6R,7Z,9Z,11E,13E,15S,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphinic acid

Formula: C43H76NO11P (813.5156)
Chinese Name:
BioDeep ID: BioDeep_00000186156 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCC[C@@H](O)[C@H](O)\C=C/C=C\C=C\C=C\[C@@H](O)C\C=C/CC



Found 15 Sample Hits

m/z Adducts Species Organ Scanning Sample
814.5297 [M+H]+
PPM:8.4
Mus musculus Kidney MALDI (CHCA)
FULL_MS_centriod_CHCA_20210819 - FULL_MS_centriod_CHCA_20210819
Resolution: 17μm, 638x437

Description

AP-MALDI instrument demo test, mass spectrum scan in centroid mode.

813.5316 [M-H2O+NH4]+
PPM:8.9
Mus musculus Left upper arm MALDI (CHCA)
357_l_total ion count - Limb defect imaging - Monash University
Resolution: 50μm, 97x131

Description

Diseased

831.5618 [M+NH4]+
PPM:14.9
Mus musculus Lung MALDI (DHB)
image3 - MTBLS2075
Resolution: 40μm, 146x190

Description

Fig. 4 MALDI-MSI data of mouse lung tissue after administration with D9-choline and U13C-DPPC–containing Poractant alfa surfactant (labels administered 12 h prior to tissue collection). Ion images of (A) m/z 796.6856 ([U13C-DPPC+Na]+), (B) m/z 756.5154 [PC32:0+Na]+), and (C) m/z 765.6079 ([D9-PC32:0+Na]+). D: Overlay image of [U13C-PC32:0+Na]+ (red) and [D9-PC32:0+Na]+ (green). Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

831.5618 [M+NH4]+
PPM:14.9
Mus musculus Lung MALDI (DHB)
image4 - MTBLS2075
Resolution: 40μm, 162x156

Description

Fig 6c Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

831.5341 [M+NH4]+
PPM:18.4
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

831.5349 [M+NH4]+
PPM:17.4
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

814.5276 [M+H]+
PPM:5.8
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

814.5325 [M+H]+
PPM:11.8
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).

836.5094 [M+Na]+
PPM:5.5
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).

813.5484 [M-H2O+NH4]+
PPM:11.8
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

814.5253 [M+H]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

814.5272 [M+H]+
PPM:5.3
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

814.5287 [M+H]+
PPM:7.2
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

814.5275 [M+H]+
PPM:5.7
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

814.5257 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description


PE(18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)) is an oxidized phosphatidylethanolamine (PE). Oxidized phosphatidylethanolamines are glycerophospholipids in which a phosphorylethanolamine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylethanolamines 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, phosphatidylethanolamines 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. PE(18:0/20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)), in particular, consists of one chain of one octadecanoyl at the C-1 position and one chain of Lipoxin A5 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 PEs can be synthesized via three different routes. In one route, the oxidized PE is synthetized de novo following the same mechanisms as for PEs 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 PE backbone, mainly through the action of LOX (PMID: 33329396).