PI(20:1(11Z)/20:4(8Z,11Z,14Z,17Z))

[(2R)-3-[(11Z)-icos-11-enoyloxy]-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propoxy]({[(1s,3R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid

Formula: C49H85O13P (912.5727)
Chinese Name:
BioDeep ID: BioDeep_00000019310 ( View LC/MS Profile)
SMILES: [H]OC1([H])C([H])(O[H])C([H])(O[H])[C@]([H])(OP(=O)(O[H])OC([H])([H])[C@]([H])(OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])[H])C([H])([H])OC(=O)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(\[H])=C(\[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])C([H])(O[H])[C@]1([H])O[H]



Found 31 Sample Hits

m/z Adducts Species Organ Scanning Sample
877.5736 [M+H-2H2O]+
PPM:16.8
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

877.5737 [M+H-2H2O]+
PPM:16.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

877.5732 [M+H-2H2O]+
PPM:16.3
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

877.5733 [M+H-2H2O]+
PPM:16.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

877.5734 [M+H-2H2O]+
PPM:16.5
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_48 - MTBLS58
Resolution: 17μm, 294x107

Description

895.5817 [M+H-H2O]+
PPM:13.7
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

895.5822 [M+H-H2O]+
PPM:14.2
Mus musculus Lung MALDI (DHB)
image3 - MTBLS2075
Resolution: 40μm, 146x190

Description

Fig. 4 MALDI-MSI data of mouse lung tissue after administration with D9-choline and U13C-DPPC–containing Poractant alfa surfactant (labels administered 12 h prior to tissue collection). Ion images of (A) m/z 796.6856 ([U13C-DPPC+Na]+), (B) m/z 756.5154 [PC32:0+Na]+), and (C) m/z 765.6079 ([D9-PC32:0+Na]+). D: Overlay image of [U13C-PC32:0+Na]+ (red) and [D9-PC32:0+Na]+ (green). 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. MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

895.5792 [M+H-H2O]+
PPM:10.9
Mus musculus Lung MALDI (DHB)
image4 - MTBLS2075
Resolution: 40μm, 162x156

Description

Fig 6c Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC.

895.5823 [M+H-H2O]+
PPM:14.3
Mus musculus Lung MALDI (DHB)
image5 - MTBLS2075
Resolution: 40μm, 163x183

Description

Supplementary Figure S8. MALDI-MSI data of mouse lung tissue administered with D9-choline and U 13C-DPPC–containing Poractant alfa surfactant (labels administered 18 h prior to sacrifice). Ion images of (a) m/z 796.6856 ([U13C-DPPC+Na]+), (b) m/z 756.5154 [PC32:0+Na]+ and (c) m/z 765.6079 ([D9-PC32:0+Na]+). (d) Overlay image of [U13C-DPPC+Na]+ (red) and [D9-PC32:0+Na]+ (green). Parts per million (ppm) mass errors are indicated in parentheses. All images were visualised using totalion-current normalisation and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0.

877.5474 [M+H-2H2O]+
PPM:13.1
Homo sapiens esophagus DESI ()
LNTO22_1_3 - MTBLS385
Resolution: 75μm, 121x68

Description

913.5844 [M+H]+
PPM:4.8
Homo sapiens esophagus DESI ()
LNTO29_16_2 - MTBLS385
Resolution: 17μm, 95x101

Description

913.5847 [M+H]+
PPM:5.1
Homo sapiens esophagus DESI ()
LNTO22_1_9 - MTBLS385
Resolution: 75μm, 89x74

Description

912.5992 [M-H2O+NH4]+
PPM:3.5
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).

912.5998 [M-H2O+NH4]+
PPM:4.2
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

913.5834 [M+H]+
PPM:3.7
Homo sapiens esophagus DESI ()
LNTO29_16_3 - MTBLS385
Resolution: 17μm, 108x107

Description

913.5843 [M+H]+
PPM:4.7
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

913.5851 [M+H]+
PPM:5.6
Homo sapiens esophagus DESI ()
LNTO26_7_2 - MTBLS385
Resolution: 17μm, 135x101

Description

913.584 [M+H]+
PPM:4.4
Homo sapiens esophagus DESI ()
LNTO26_7_3 - MTBLS385
Resolution: 75μm, 82x88

Description

913.5835 [M+H]+
PPM:3.8
Homo sapiens esophagus DESI ()
TO31T - MTBLS385
Resolution: 75μm, 56x54

Description

913.5846 [M+H]+
PPM:5
Homo sapiens esophagus DESI ()
TO29T - MTBLS385
Resolution: 75μm, 56x48

Description

913.5835 [M+H]+
PPM:3.8
Homo sapiens esophagus DESI ()
LNTO30_8M_2 - MTBLS385
Resolution: 75μm, 108x68

Description

913.5836 [M+H]+
PPM:3.9
Homo sapiens esophagus DESI ()
LNTO30_8M_3 - MTBLS385
Resolution: 75μm, 69x54

Description

913.5843 [M+H]+
PPM:4.7
Homo sapiens esophagus DESI ()
LNTO30_8M_4 - MTBLS385
Resolution: 75μm, 62x48

Description

913.5841 [M+H]+
PPM:4.5
Homo sapiens esophagus DESI ()
LNTO30_8M_5 - MTBLS385
Resolution: 75μm, 56x54

Description

913.5838 [M+H]+
PPM:4.1
Homo sapiens esophagus DESI ()
LNTO30_17_2 - MTBLS385
Resolution: 75μm, 82x54

Description

913.5848 [M+H]+
PPM:5.2
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

913.584 [M+H]+
PPM:4.4
Homo sapiens esophagus DESI ()
LNTO22_2_1 - MTBLS385
Resolution: 75μm, 89x88

Description

913.5846 [M+H]+
PPM:5
Homo sapiens esophagus DESI ()
LNTO22_2_2 - MTBLS385
Resolution: 75μm, 135x94

Description

913.5843 [M+H]+
PPM:4.7
Homo sapiens esophagus DESI ()
LNTO26_16_1 - MTBLS385
Resolution: 75μm, 95x88

Description

913.5834 [M+H]+
PPM:3.7
Homo sapiens esophagus DESI ()
LNTO30_7_1 - MTBLS385
Resolution: 75μm, 69x68

Description

913.5838 [M+H]+
PPM:4.1
Homo sapiens esophagus DESI ()
LNTO30_7_2 - MTBLS385
Resolution: 75μm, 82x68

Description


PI(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylinositol. 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. Fatty acids containing 18 and 20 carbons are the most common. PI(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicosenoic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The eicosenoic acid moiety is derived from vegetable oils and cod oils, while the eicsoatetraenoic acid moiety is derived from fish oils. 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 contain almost exclusively stearic acid at carbon 1 and arachidonic acid at carbon 2. 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. PI(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)) is a phosphatidylinositol. 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. Fatty acids containing 18 and 20 carbons are the most common. PI(20:1(11Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of eicosenoic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The eicosenoic acid moiety is derived from vegetable oils and cod oils, while the eicsoatetraenoic acid moiety is derived from fish oils. In most organisms, the stereochemical form of the last is myo-D-inositol (with one axial hydroxyl in position 2 with the remainder equatorial. 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.