1-palmitoylplasmenylethanolamine

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  • Name: 1-palmitoylplasmenylethanolamine
  • Description: 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether ... linkage, as opposed to the usual ester linkage. 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. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. (HMDB0011152)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
27374292 Age [25–35] (median=32), Gender ♀ 0.733886 (mean value of the compound area) LC/MS Neg serum
27374292 Age [55-65] (median=60), Gender ♀ 1.004405 (mean value of the compound area) LC/MS Neg serum
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    PE(P-16:0);PE(P-16:0/0:0);PE(P-16:0e/0:0)
  • Chemical Formula:
    C21H44NO6P
  • Systematic name:
    2-aminoethyl [(2R)-3-[(Z)-hexadec-1-enoxy]-2-hydroxypropyl] hydrogen phosphate
  • SMILES:
    CCCCCCCCCCCCCCC=COCC(COP(=O)(O)OCCN)O
  • InChI:
    InChI=1S/C21H44NO6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-26-19-21(23)20-28-29(24,25)27-18-16-22/h15,17,21,23H,2-14,16,18-20,22H2,1H3,(H,24,25)/b17-15-/t21-/m1/s1
  • InChI Key:
    QYTPGOPLNFESQC-NUTQULCTSA-N
Related resources
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Extracellular, Human body biofluids, Biofluid tissues, Blood, Serum, Tissue, Cellular (general class), Subcellular, Cell membrane, Excreta material, Feces
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Age group comparisons
Method: LC/MS Neg
Sample: serum
PubMed PMID: 27374292
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