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

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

Formula: C33H63O10P (650.4159)
Chinese Name:
BioDeep ID: BioDeep_00000187796 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC[C@H](O)[C@@H](O)C\C=C/CCCCC



Found 6 Sample Hits

m/z Adducts Species Organ Scanning Sample
651.4336 [M+H]+
PPM:16.1
Mus musculus Left upper arm MALDI (CHCA)
357_l_total ion count - Limb defect imaging - Monash University
Resolution: 50μm, 97x131

Description

Diseased

668.4404 [M+NH4]+
PPM:13.9
Mus musculus Left upper arm MALDI (CHCA)
357_l_total ion count - Limb defect imaging - Monash University
Resolution: 50μm, 97x131

Description

Diseased

633.4051 [M+H-H2O]+
PPM:11.8
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

668.4465 [M+NH4]+
PPM:4.8
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

650.4184 [M]+
PPM:4.7
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).

651.4279 [M+H]+
PPM:7.3
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description


PA(12:0/18:1(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(12:0/18:1(12Z)-2OH(9,10)), in particular, consists of one chain of one dodecanoyl 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).