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

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

Formula: C42H78NO11P (803.5312)
Chinese Name:
BioDeep ID: BioDeep_00000206370 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC



Found 23 Sample Hits

m/z Adducts Species Organ Scanning Sample
804.5398 [M+H]+
PPM:1.6
Mus musculus Urinary bladder MALDI (CHCA)
HR2MSI_mouse_urinary_bladder - S096 - PXD001283
Resolution: 10μm, 260x134

Description

Mass spectrometry imaging of phospholipids in mouse urinary bladder (imzML dataset)
The spatial distribution of phospholipids in a tissue section of mouse urinary bladder was analyzed by MALDI MS imaging at 10 micrometer pixel size with high mass resolution (using an LTQ Orbitrap mass spectrometer).

R, ö, mpp A, Guenther S, Schober Y, Schulz O, Takats Z, Kummer W, Spengler B, Histology by mass spectrometry: label-free tissue characterization obtained from high-accuracy bioanalytical imaging. Angew Chem Int Ed Engl, 49(22):3834-8(2010)

Fig. S2: Single ion images of compounds shown in Fig. 1A-B : (upper left to lower right) m/z = 743.5482 (unknown), m/z = 741.5307 (SM (16:0), [M+K]+), m/z = 798.5410 (PC (34:1), [M+K]+), m/z = 616.1767 (heme b, M+), m/z = 772.5253 (PC (32:0), [M+K]+).

Stability of determined mass values was in the range of +/- 1 ppm over 22 hours of measurement (Fig. S4), with a standard deviation of 0.56 ppm. Accuracy data were obtained during tissue scanning experiments by monitoring the mass signal at nominal mass 798. The internal lock mass function of the Orbitrap instrument was used for automatic calibration during imaging measurements, using the known matrix-related ion signals at m/z = 137.0233, m/z = 444.0925 and m/z = 716.1246.

826.5309 [M+Na]+
PPM:12.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

826.5311 [M+Na]+
PPM:12.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

826.531 [M+Na]+
PPM:12.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

826.5304 [M+Na]+
PPM:12
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_48 - MTBLS58
Resolution: 17μm, 294x107

Description

826.5305 [M+Na]+
PPM:12.2
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

826.5302 [M+Na]+
PPM:11.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

826.5322 [M+Na]+
PPM:14.2
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

826.5309 [M+Na]+
PPM:12.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

826.5322 [M+Na]+
PPM:14.2
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

804.551 [M+H]+
PPM:15.5
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

804.5425 [M+H]+
PPM:5
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

804.5305 [M+H]+
PPM:9.9
Mytilus edulis mantle MALDI (DHB)
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960
Resolution: 10μm, 275x210

Description

804.5438 [M+H]+
PPM:6.6
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

804.5415 [M+H]+
PPM:3.7
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

804.5402 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

804.5407 [M+H]+
PPM:2.7
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

804.5406 [M+H]+
PPM:2.6
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

804.5422 [M+H]+
PPM:4.6
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

804.5424 [M+H]+
PPM:4.9
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

804.5426 [M+H]+
PPM:5.1
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

804.5424 [M+H]+
PPM:4.9
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

804.5403 [M+H]+
PPM:2.2
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description


PS(18:0/18:1(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(18:0/18:1(12Z)-O(9S,10R)), in particular, consists of one chain of one octadecanoyl 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).