PI(18:0/20:4(6E,8Z,11Z,14Z)+=O(5))

[(2R)-3-(octadecanoyloxy)-2-{[(6E,8Z,11Z,14Z)-5-oxoicosa-6,8,11,14-tetraenoyl]oxy}propoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Formula: C47H81O14P (900.5364)
Chinese Name:
BioDeep ID: BioDeep_00000201382 ( View LC/MS Profile)
SMILES: [H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O)OC(=O)CCCC(=O)\C=C\C=C/C\C=C/C\C=C/CCCCC



Found 67 Sample Hits

m/z Adducts Species Organ Scanning Sample
918.5728 [M+NH4]+
PPM:2.8
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.

901.5415 [M+H]+
PPM:2.4
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

883.5359 [M+H-H2O]+
PPM:3.2
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

901.5465 [M+H]+
PPM:3.2
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

918.5539 [M+NH4]+
PPM:17.7
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

883.5347 [M+H-H2O]+
PPM:1.8
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

901.5455 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

883.5336 [M+H-H2O]+
PPM:0.6
Homo sapiens esophagus DESI ()
TO42T - MTBLS385
Resolution: 17μm, 69x81

Description

883.5367 [M+H-H2O]+
PPM:4.1
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

901.5475 [M+H]+
PPM:4.3
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

883.5345 [M+H-H2O]+
PPM:1.6
Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

901.5452 [M+H]+
PPM:1.7
Homo sapiens esophagus DESI ()
LNTO30_8M_1 - MTBLS385
Resolution: 17μm, 69x54

Description

883.5338 [M+H-H2O]+
PPM:0.8
Homo sapiens esophagus DESI ()
TO39T - MTBLS385
Resolution: 17μm, 69x81

Description

865.5129 [M+H-2H2O]+
PPM:11.1
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).

901.5449 [M+H]+
PPM:1.4
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).

883.5331 [M+H-H2O]+
PPM:
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).

883.5357 [M+H-H2O]+
PPM:3
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).

883.536 [M+H-H2O]+
PPM:3.3
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

883.5343 [M+H-H2O]+
PPM:1.4
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

901.5449 [M+H]+
PPM:1.4
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

883.5361 [M+H-H2O]+
PPM:3.4
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

901.5466 [M+H]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

883.5369 [M+H-H2O]+
PPM:4.3
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

901.5475 [M+H]+
PPM:4.3
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

883.5357 [M+H-H2O]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

901.5463 [M+H]+
PPM:2.9
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

883.5343 [M+H-H2O]+
PPM:1.4
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

901.5452 [M+H]+
PPM:1.7
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

883.5359 [M+H-H2O]+
PPM:3.2
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

901.5464 [M+H]+
PPM:3.1
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

883.5345 [M+H-H2O]+
PPM:1.6
Homo sapiens esophagus DESI ()
TO41T - MTBLS385
Resolution: 75μm, 69x43

Description

883.5348 [M+H-H2O]+
PPM:2
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

901.5455 [M+H]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

883.5345 [M+H-H2O]+
PPM:1.6
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

901.5452 [M+H]+
PPM:1.7
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

883.5351 [M+H-H2O]+
PPM:2.3
Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

901.5461 [M+H]+
PPM:2.7
Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

883.5349 [M+H-H2O]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

901.5458 [M+H]+
PPM:2.4
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

883.5349 [M+H-H2O]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

901.5457 [M+H]+
PPM:2.3
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

883.5363 [M+H-H2O]+
PPM:3.6
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

901.5468 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

883.536 [M+H-H2O]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

901.5465 [M+H]+
PPM:3.2
Homo sapiens esophagus DESI ()
LNTO22_1_7 - MTBLS385
Resolution: 75μm, 69x54

Description

883.5357 [M+H-H2O]+
PPM:3
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

900.5695 [M-H2O+NH4]+
PPM:11
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

901.5463 [M+H]+
PPM:2.9
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

883.5356 [M+H-H2O]+
PPM:2.9
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

901.5461 [M+H]+
PPM:2.7
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

883.5362 [M+H-H2O]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

900.5698 [M-H2O+NH4]+
PPM:11.3
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

901.5468 [M+H]+
PPM:3.5
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

883.536 [M+H-H2O]+
PPM:3.3
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

901.5464 [M+H]+
PPM:3.1
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

883.5344 [M+H-H2O]+
PPM:1.5
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

901.5449 [M+H]+
PPM:1.4
Homo sapiens esophagus DESI ()
LNTO29_18_2 - MTBLS385
Resolution: 75μm, 62x68

Description

883.5349 [M+H-H2O]+
PPM:2.1
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

901.5456 [M+H]+
PPM:2.2
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

883.5345 [M+H-H2O]+
PPM:1.6
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description

883.5343 [M+H-H2O]+
PPM:1.4
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

901.5449 [M+H]+
PPM:1.4
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

883.535 [M+H-H2O]+
PPM:2.2
Homo sapiens colorectal adenocarcinoma DESI ()
200TopL, 170TopR, 190BottomL, 180BottomR-centroid - MTBLS176
Resolution: 50μm, 132x126

Description

883.5341 [M+H-H2O]+
PPM:1.2
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

901.5445 [M+H]+
PPM:1
Homo sapiens colorectal adenocarcinoma DESI ()
160TopL,130TopR,150BottomL,140BottomR-centroid - MTBLS176
Resolution: 50μm, 142x136

Description

883.5347 [M+H-H2O]+
PPM:1.8
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description

901.5455 [M+H]+
PPM:2.1
Homo sapiens colorectal adenocarcinoma DESI ()
120TopL, 90TopR, 110BottomL, 100BottomR-centroid - MTBLS176
Resolution: 50μm, 132x136

Description


PI(18:0/20:4(6E,8Z,11Z,14Z)+=O(5)) is an oxidized phosphatidylinositol (PI). Phosphatidylinositols are important lipids, both as a key membrane constituent and as a participant in essential metabolic processes, both directly and via a number of metabolites. Phosphatidylinositols are acidic (anionic) phospholipids that consist of a phosphatidic acid backbone, linked via the phosphate group to inositol (hexahydroxycyclohexane). Phosphatidylinositols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PI(18:0/20:4(6E,8Z,11Z,14Z)+=O(5)), in particular, consists of one chain of octadecanoyl at the C-1 position and one chain of 5-oxo-eicosatetraenoyl at the C-2 position. The inositol group that is part of every phosphatidylinositol lipid is covalently linked to the phosphate group that acts as a bridge to the lipid tail. In most organisms, the stereochemical form of this inositol is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial), although other forms can be found in certain plant phosphatidylinositols. Phosphatidylinositol is especially abundant in brain tissue, where it can amount to 10\\% of the phospholipids, but it is present in all tissues and cell types. There is usually less of it than of phosphatidylcholine, phosphatidylethanolamine and phosphatidylserine. In animal tissues, phosphatidylinositol is the primary source of the arachidonic acid required for biosynthesis of eicosanoids, including prostaglandins, via the action of the enzyme phospholipase A2. Phosphatidylinositol can be phosphorylated by a number of different kinases that place the phosphate moiety on positions 4 and 5 of the inositol ring, although position 3 can also be phosphorylated by a specific kinase. Seven different isomers are known, but the most important in both quantitative and biological terms are phosphatidylinositol 4-phosphate and phosphatidylinositol 4,5-bisphosphate. Phosphatidylinositol and the phosphatidylinositol phosphates are the main source of diacylglycerols that serve as signaling molecules, via the action of phospholipase C enzymes. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PIs composed exclusively of non-phosphorylated inositol exhibit a net charge of -1 at physiological pH. Molecules with phosphorylated inositol (such as PIP, PIP2, PIP3, etc.) are termed polyphosphoinositides. The polyphosphoinositides are important intracellular transducers of signals emanating from the plasma membrane. The synthesis of PI involves CDP-activated 1,2-diacylglycerol condensation with myo-inositol.