sphingomyeline C18:1

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  • Name: sphingomyeline C18:1
  • Description: Sphingomyelin (d18:1/18:1(9Z))or SM(d18:1/18:1(9Z)) is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. It us... ually consists of phosphorylcholine and ceramide. In humans, sphingomyelin is the only membrane phospholipid not derived from glycerol. Like all sphingolipids, SPH 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 localise 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. (HMDB0012101)
Overview of age-variations
Age group comparisons
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Linear regression
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
22834969 Age 54.1 ± 13.1, Gender ♀ 1.32 (β) FIA-MS/MS serum
22834969 Age 57.7 ± 10.6, Gender ♀ 0.42 (β) FIA-MS/MS serum
log2 ratio/log2(FC)
PMID Age/Age interval, Gender Value (unit of measurement) Method Sample
Summary
  • Synonym:
    SM C18:1; C18:1 sphingomyelin
  • Chemical Formula:
    C41H81N2O6P
  • Exact Mass g/mol:
    728.5830000
  • Systematic name:
    [(E,2S,3R)-3-hydroxy-2-[[(Z)-octadec-9-enoyl]amino]octadec-4-enyl] 2-(trimethylazaniumyl)ethyl phosphate
  • SMILES:
    CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)([O-])OCC[N+](C)(C)C)NC(=O)CCCCCCC/C=C\CCCCCCCC)O
  • InChI:
    InChI=1S/C41H81N2O6P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-41(45)42-39(38-49-50(46,47)48-37-36-43(3,4)5)40(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,32,34,39-40,44H,6-19,22-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b21-20-,34-32+/t39-,40+/m0/s1
  • InChI Key:
    NBEADXWAAWCCDG-QDDWGVBQSA-N
  • CAS number:
    108392-10-5
Related resources
Metabolite sources and localization
  • Metabolite location:
    Human organism, Body part, Human body biofluids, Biofluid tissues, Blood, Serum, Cerebrospinal fluid, Saliva, Urine, Tissue, Excreta material, Feces
  • Metabolite source:
    Homo sapiens, endogenous metabolite
Age-variations
Linear regression
Method: FIA-MS/MS
Sample: serum
PubMed PMID: 22834969
β = 1.32 (y = βx + α)
p-value < 0.05
Linear regression
Method: FIA-MS/MS
Sample: serum
PubMed PMID: 22834969
β = 0.42 (y = βx + α)
p-value < 0.05
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