PS(22:0/18:1(12Z)-O(9S,10R))

(2S)-2-amino-3-({[(2R)-3-(docosanoyloxy)-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy](hydroxy)phosphoryl}oxy)propanoic acid

Formula: C46H86NO11P (859.5938)
Chinese Name:
BioDeep ID: BioDeep_00000207928 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCCCCCC)(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC



Found 15 Sample Hits

m/z Adducts Species Organ Scanning Sample
859.617 [M-H2O+NH4]+
PPM:0.1
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

859.6169 [M-H2O+NH4]+
PPM:0.2
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

859.6164 [M-H2O+NH4]+
PPM:0.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

859.6165 [M-H2O+NH4]+
PPM:0.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

859.6164 [M-H2O+NH4]+
PPM:0.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_48 - MTBLS58
Resolution: 17μm, 294x107

Description

859.6163 [M-H2O+NH4]+
PPM:0.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

859.6162 [M-H2O+NH4]+
PPM:1
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

859.6166 [M-H2O+NH4]+
PPM:0.6
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

859.6165 [M-H2O+NH4]+
PPM:0.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

859.6168 [M-H2O+NH4]+
PPM:0.3
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

860.6105 [M+H]+
PPM:10.9
Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

860.6111 [M+H]+
PPM:11.6
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

860.6112 [M+H]+
PPM:11.7
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

860.6103 [M+H]+
PPM:10.7
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

877.6374 [M+NH4]+
PPM:11.1
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description


PS(22:0/18:1(12Z)-O(9S,10R)) is an oxidized phosphatidylserine (PS). Oxidized phosphatidylserines are glycerophospholipids in which a phosphorylserine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylserines 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, phosphatidylserines 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. PS(22:0/18:1(12Z)-O(9S,10R)), in particular, consists of one chain of one docosanoyl at the C-1 position and one chain of 9,10-epoxy-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 PSs can be synthesized via three different routes. In one route, the oxidized PS is synthetized de novo following the same mechanisms as for PSs 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 PS backbone, mainly through the action of LOX (PMID: 33329396).