PA(19:0/PGF1alpha)

[(2R)-2-({7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]heptanoyl}oxy)-3-(nonadecanoyloxy)propoxy]phosphonic acid

Formula: C42H79O11P (790.536)
Chinese Name:
BioDeep ID: BioDeep_00000189500 ( View LC/MS Profile)
SMILES: CCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCC[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCCCC



Found 58 Sample Hits

m/z Adducts Species Organ Scanning Sample
808.5722 [M+NH4]+
PPM:3
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.

791.5391 [M+H]+
PPM:5.2
Homo sapiens Liver MALDI (DHB)
20171107_FIT4_DHBpos_p70_s50 - Rappez et al (2021) SpaceM reveals metabolic states of single cells
Resolution: 50μm, 70x70

Description

791.5391 [M+H]+
PPM:5.2
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_17 - MTBLS58
Resolution: 17μm, 208x108

Description

1 male adult wild-type rat was obtained from Inserm U1085 - Irset Research Institute (University of Rennes1, France). Animals were age 60 days and were reared under ad-lib conditions. Care and handling of all animals complied with EU directive 2010/63/EU on the protection of animals used for scientific purposes. The whole epididymis was excised from each animal immediately post-mortem, loosely wrapped rapidly in an aluminum foil and a 2.5% (w/v) carboxymethylcellulose (CMC) solution was poured to embed the epididymis to preserve their morphology. To remove air bubbles, the filled aluminum molds was gently freezed by depositing it on isopentane or dry ice, then on the nitrogen vapors and finally by progressively dipping the CMC/sample coated with aluminum foil into liquid nitrogen (or only flush with liquid nitrogen). Frozen tissues were stored at -80 °C until use to avoid degradation.

791.539 [M+H]+
PPM:5.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

791.539 [M+H]+
PPM:5.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

791.5389 [M+H]+
PPM:5.5
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

791.5386 [M+H]+
PPM:5.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

791.5387 [M+H]+
PPM:5.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

791.5385 [M+H]+
PPM:6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_48 - MTBLS58
Resolution: 17μm, 294x107

Description

791.5387 [M+H]+
PPM:5.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

791.5386 [M+H]+
PPM:5.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

791.5388 [M+H]+
PPM:5.6
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

791.5388 [M+H]+
PPM:5.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

791.5388 [M+H]+
PPM:5.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

791.5575 [M+H]+
PPM:18
Mus musculus Lung MALDI (DHB)
image1 - MTBLS2075
Resolution: 40μm, 187x165

Description

Fig. 2 MALDI-MSI data from the same mouse lung tissue analyzed in Fig. 1. A: Optical image of the post-MSI, H&E-stained tissue section. B–D, F–G: Ion images of (B) m/z 796.6855 ([U13C-DPPC+Na]+), (C) m/z 756.5514 ([PC32:0+Na]+), (D) m/z 765.6079 ([D9-PC32:0+Na]+), (F) m/z 754.5359 ([PC32:1+Na]+), and (G) m/z 763.5923 ([D9-PC32:1+Na]+). E, H: Ratio images of (E) [D9-PC32:0+Na]+:[PC32:0+Na]+ and (H) [D9-PC32:1+Na]+:[PC32:1+Na]+. 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. U13C-DPPC, universally 13C-labeled dipalmitoyl PC; PC, phosphatidylcholine; MSI, mass spectrometry imaging; H&E, hematoxylin and eosin. Fig 1-3, Fig S1-S3, S5

790.5523 [M-H2O+NH4]+
PPM:8.8
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

791.5462 [M+H]+
PPM:3.7
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

791.5444 [M+H]+
PPM:1.5
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

791.5407 [M+H]+
PPM:3.2
Homo sapiens esophagus DESI ()
LNTO22_1_4 - MTBLS385
Resolution: 17μm, 82x80

Description

791.5431 [M+H]+
PPM:0.2
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

791.5421 [M+H]+
PPM:1.5
Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

791.5453 [M+H]+
PPM:2.6
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

791.5433 [M+H]+
PPM:0.1
Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

791.5426 [M+H]+
PPM:0.8
Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

791.5452 [M+H]+
PPM:2.5
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).

791.5414 [M+H]+
PPM:2.3
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).

791.5407 [M+H]+
PPM:3.2
Homo sapiens colorectal adenocarcinoma DESI ()
439TopL, 409TopR, 429BottomL, 419BottomR-profile - MTBLS415
Resolution: 17μm, 157x136

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).

791.5434 [M+H]+
PPM:0.2
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

791.5427 [M+H]+
PPM:0.7
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

790.5427 [M]+
PPM:9.2
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

791.5453 [M+H]+
PPM:2.6
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

791.546 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

790.5432 [M]+
PPM:9.8
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

791.5449 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

790.5409 [M]+
PPM:6.9
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

791.5434 [M+H]+
PPM:0.2
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

791.5441 [M+H]+
PPM:1.1
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

791.543 [M+H]+
PPM:0.3
Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

791.5435 [M+H]+
PPM:0.3
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

790.5412 [M]+
PPM:7.3
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

791.5435 [M+H]+
PPM:0.3
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

791.5436 [M+H]+
PPM:0.4
Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

791.5437 [M+H]+
PPM:0.6
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

791.5436 [M+H]+
PPM:0.4
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

791.5449 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

791.5443 [M+H]+
PPM:1.3
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

791.5441 [M+H]+
PPM:1.1
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

791.5445 [M+H]+
PPM:1.6
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

791.5447 [M+H]+
PPM:1.8
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

791.5448 [M+H]+
PPM:2
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

791.5428 [M+H]+
PPM:0.6
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

791.5435 [M+H]+
PPM:0.3
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

791.5433 [M+H]+
PPM:0.1
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

790.5513 [M-H2O+NH4]+
PPM:10
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

791.5429 [M+H]+
PPM:0.4
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

791.5435 [M+H]+
PPM:0.3
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

791.5428 [M+H]+
PPM:0.6
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

791.5433 [M+H]+
PPM:0.1
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


PA(19:0/PGF1alpha) 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(19:0/PGF1alpha), in particular, consists of one chain of one nonadecanoyl at the C-1 position and one chain of 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 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).