PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

(2-{[(2R)-2-[(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoyloxy]-3-[(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Formula: C48H76NO8P (825.5308)
Chinese Name:
BioDeep ID: BioDeep_00000029518 ( View LC/MS Profile)
SMILES: CC\C=C/C\C=C/C\C=C/C\C=C/CCCCC(=O)OC[C@]([H])(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC



Found 47 Sample Hits

m/z Adducts Species Organ Scanning Sample
826.5512 [M+H]+
PPM:15.8
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.

790.5144 [M+H-2H2O]+
PPM:3.3
Rattus norvegicus Brain MALDI (CHCA)
Spectroswiss - sol_2x_br_2 - 2016-09-29_07h40m45s
Resolution: 17μm, 488x193

Description

826.5525 [M+H]+
PPM:17.4
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.

848.5358 [M+Na]+
PPM:18.6
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.

826.5521 [M+H]+
PPM:16.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

848.5347 [M+Na]+
PPM:17.3
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_18 - MTBLS58
Resolution: 17μm, 208x104

Description

826.5456 [M+H]+
PPM:16.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

848.5356 [M+Na]+
PPM:18.3
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_43 - MTBLS58
Resolution: 17μm, 298x106

Description

826.5521 [M+H]+
PPM:16.9
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_44 - MTBLS58
Resolution: 17μm, 299x111

Description

826.5502 [M+H]+
PPM:14.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_46 - MTBLS58
Resolution: 17μm, 298x106

Description

826.5516 [M+H]+
PPM:16.3
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_47 - MTBLS58
Resolution: 17μm, 301x111

Description

826.5511 [M+H]+
PPM:15.7
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito08_48 - MTBLS58
Resolution: 17μm, 294x107

Description

826.5517 [M+H]+
PPM:16.5
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

848.5354 [M+Na]+
PPM:18.1
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_04 - MTBLS58
Resolution: 17μm, 178x91

Description

826.5508 [M+H]+
PPM:15.4
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_03 - MTBLS58
Resolution: 17μm, 159x110

Description

826.5521 [M+H]+
PPM:16.9
Rattus norvegicus normal MALDI (DHB)
epik_dhb_head_ito01_05 - MTBLS58
Resolution: 17μm, 183x105

Description

826.5517 [M+H]+
PPM:16.5
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito01_06 - MTBLS58
Resolution: 17μm, 183x103

Description

826.5518 [M+H]+
PPM:16.6
Rattus norvegicus Epididymis MALDI (DHB)
epik_dhb_head_ito03_14 - MTBLS58
Resolution: 17μm, 205x103

Description

790.5123 [M+H-2H2O]+
PPM:5.9
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

843.5566 [M+NH4]+
PPM:9.5
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

790.5154 [M+H-2H2O]+
PPM:2
Mus musculus Left upper arm MALDI (CHCA)
357_l_total ion count - Limb defect imaging - Monash University
Resolution: 50μm, 97x131

Description

Diseased

826.5335 [M+H]+
PPM:5.6
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.

843.5567 [M+NH4]+
PPM:9.4
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.

790.511 [M+H-2H2O]+
PPM:7.6
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.

790.5145 [M+H-2H2O]+
PPM:3.1
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.

843.5566 [M+NH4]+
PPM:9.5
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.

790.5163 [M+H-2H2O]+
PPM:0.9
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

826.5458 [M+H]+
PPM:9.3
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

790.5267 [M+H-2H2O]+
PPM:12.3
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).

843.5492 [M+NH4]+
PPM:18.3
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).

790.5149 [M+H-2H2O]+
PPM:2.6
Mytilus edulis mantle MALDI (DHB)
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960
Resolution: 10μm, 275x210

Description

790.5267 [M+H-2H2O]+
PPM:12.3
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).

790.5262 [M+H-2H2O]+
PPM:11.7
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).

826.5243 [M+H]+
PPM:16.7
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).

843.5576 [M+NH4]+
PPM:8.4
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).

843.5485 [M+NH4]+
PPM:19.1
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).

790.5287 [M+H-2H2O]+
PPM:14.8
Homo sapiens NA DESI ()
160TopL,130TopR,150BottomL,140BottomR-profile - MTBLS415
Resolution: 17μm, 142x136

Description

826.5265 [M+H]+
PPM:14
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

843.5519 [M+NH4]+
PPM:15.1
Homo sapiens esophagus DESI ()
LNTO26_7_1 - MTBLS385
Resolution: 17μm, 75x74

Description

843.5524 [M+NH4]+
PPM:14.5
Homo sapiens esophagus DESI ()
LNTO22_1_5 - MTBLS385
Resolution: 75μm, 135x94

Description

826.527 [M+H]+
PPM:13.4
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

843.5514 [M+NH4]+
PPM:15.7
Homo sapiens esophagus DESI ()
LNTO22_1_8 - MTBLS385
Resolution: 75μm, 69x61

Description

790.5026 [M+H-2H2O]+
PPM:18.2
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_02_centroid - MTBLS313
Resolution: 17μm, 434x258

Description

790.5163 [M+H-2H2O]+
PPM:0.9
Mus musculus brain MALDI (DHB)
Brain01_Bregma1-42_01_centroid - MTBLS313
Resolution: 17μm, 447x118

Description

790.515 [M+H-2H2O]+
PPM:2.5
Mus musculus brain MALDI (DHB)
Brain02_Bregma1-42_03 - MTBLS313
Resolution: 17μm, 483x403

Description

790.5161 [M+H-2H2O]+
PPM:1.1
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description

843.5501 [M+NH4]+
PPM:17.3
Homo sapiens colorectal adenocarcinoma DESI ()
240TopL, 210TopR, 230BottomL, 220BottomR-centroid - MTBLS176
Resolution: 50μm, 142x141

Description


PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines 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 16, 18 and 20 carbons are the most common. PC(18:4(6Z,9Z,12Z,15Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of stearidonic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The stearidonic acid moiety is derived from seed oils, while the docosahexaenoic acid moiety is derived from fish oils. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.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. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.