PE(20:3(5Z,8Z,11Z)/6 keto-PGF1alpha)

(2-aminoethoxy)[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-6-oxoheptanoyl}oxy)-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propoxy]phosphinic acid

Formula: C45H78NO12P (855.5261)
Chinese Name:
BioDeep ID: BioDeep_00000187154 ( View LC/MS Profile)
SMILES: CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)OC[C@H](COP(O)(=O)OCCN)OC(=O)CCCCC(=O)C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC



Found 12 Sample Hits

m/z Adducts Species Organ Scanning Sample
856.5468 [M+H]+
PPM:15.6
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.

856.5352 [M+H]+
PPM:2.1
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

856.5393 [M+H]+
PPM:6.9
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

856.5423 [M+H]+
PPM:10.4
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).

856.5396 [M+H]+
PPM:7.2
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).

856.5377 [M+H]+
PPM:5
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

856.5381 [M+H]+
PPM:5.5
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

856.5383 [M+H]+
PPM:5.7
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

856.5382 [M+H]+
PPM:5.6
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

856.5391 [M+H]+
PPM:6.6
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

856.5376 [M+H]+
PPM:4.9
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

856.5379 [M+H]+
PPM:5.2
Mus musculus brain MALDI (DHB)
Brain02_Bregma-3-88 - MTBLS313
Resolution: 17μm, 288x282

Description


PE(20:3(5Z,8Z,11Z)/6 keto-PGF1alpha) 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(20:3(5Z,8Z,11Z)/6 keto-PGF1alpha), in particular, consists of one chain of one 5Z,8Z,11Z-eicosatrienoyl at the C-1 position and one chain of 6-Keto-prostaglandin F1alpha 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).