SM(d16:2(4E,8Z)/5-iso PGF2VI)

(2-{[(2S,3R,4E,8Z)-2-[(3Z)-5-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3R)-3-hydroxyoct-1-en-1-yl]cyclopentyl]pent-3-enamido]-3-hydroxyhexadeca-4,8-dien-1-yl phosphono]oxy}ethyl)trimethylazanium

Formula: C39H71N2O9P (742.4897)
Chinese Name:
BioDeep ID: BioDeep_00000215313 ( View LC/MS Profile)
SMILES: CCCCCCC\C=C/CC\C=C\[C@@H](O)[C@H](COP([O-])(=O)OCC[N+](C)(C)C)NC(=O)C\C=C/C[C@@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@H](O)CCCCC



Found 6 Sample Hits

m/z Adducts Species Organ Scanning Sample
743.4916 [M+H]+
PPM:7.2
Rattus norvegicus Brain MALDI (CHCA)
Spectroswiss - sol_2x_br_2 - 2016-09-29_07h40m45s
Resolution: 17μm, 488x193

Description

743.4889 [M+H]+
PPM:10.9
Mus musculus Lung MALDI (DHB)
image2 - MTBLS2075
Resolution: 40μm, 550x256

Description

Supplementary Figure S6. Ion distribution images for (a) [PC36:4+Na]+ (m/z 804.5514) and (b) [PC38:6+Na]+ (m/z 828.5515) obtained from mouse lung tissue collected 6 h after administration of D9- choline and U13C-DPPC–containing CHF5633. Parts-per-million (ppm) mass errors are indicated in parentheses. (c) Magnification of the boxed region in (a) with selected bronchiolar regions outlined in white boxes. (d) The corresponding H&E-stained tissue section with the same selected bronchiolar regions outlined in black boxes. These data demonstrate the co-localisation of the polyunsaturated lipids PC36:4 and PC38:6 with the bronchiolar regions of the lung. All MSI images were visualised using total ion current normalisation and hotspot removal (high quantile = 99%).

725.5008 [M+H-H2O]+
PPM:19.8
Mus musculus brain MALDI (DHB)
Brain01_Bregma-3-88b_centroid - MTBLS313
Resolution: 17μm, 265x320

Description

725.4997 [M+H-H2O]+
PPM:18.3
Mus musculus brain MALDI (DHB)
Brain02_Bregma1-42_03 - MTBLS313
Resolution: 17μm, 483x403

Description

725.4998 [M+H-H2O]+
PPM:18.5
Mus musculus brain MALDI (DHB)
Brain02_Bregma-3-88 - MTBLS313
Resolution: 17μm, 288x282

Description

725.4998 [M+H-H2O]+
PPM:18.5
Mus musculus brain MALDI (DHB)
Brain02_Bregma-1-46 - MTBLS313
Resolution: 17μm, 294x399

Description


SM(d16:2(4E,8Z)/5-iso PGF2VI) is a type of oxidized sphingolipid found in animal cell membranes. It usually consists of phosphorylcholine and ceramide. SM(d16:2(4E,8Z)/5-iso PGF2VI) consists of a sphingosine backbone and a 5-iso Prostaglandin F2alpha-VI chain. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SM has a ceramide core (sphingosine bonded to a fatty acid via an amide linkage). In addition, it contains one polar head group, which is either phosphocholine or phosphoethanolamine. The plasma membrane of cells is highly enriched in sphingomyelin and is considered largely to be found in the exoplasmic leaflet of the cell membrane. However, there is some evidence that there may also be a sphingomyelin pool in the inner leaflet of the membrane. Moreover, neutral sphingomyelinase-2, an enzyme that breaks down sphingomyelin into ceramide, has been found to localize exclusively to the inner leaflet further suggesting that there may be sphingomyelin present there. Sphingomyelin can accumulate in a rare hereditary disease called Niemann-Pick Disease, types A and B. Niemann-Pick disease is a genetically-inherited disease caused by a deficiency in the enzyme sphingomyelinase, which causes the accumulation of sphingomyelin in spleen, liver, lungs, bone marrow, and the brain, causing irreversible neurological damage. SMs play a role in signal transduction. Sphingomyelins are synthesized by the transfer of phosphorylcholine from phosphatidylcholine to a ceramide in a reaction catalyzed by sphingomyelin synthase.