Structure Database (LMSD)

Common Name
SM(d18:1/18:0)
Systematic Name
N-(octadecanoyl)-sphing-4-enine-1-phosphocholine
Synonyms
  • C18 Sphingomyelin
LM ID
LMSP03010001
Formula
Exact Mass
Calculate m/z
730.598876
Sum Composition
Abbrev Chains
SM 18:1;O2/18:0
Status
Curated


Classification

Biological Context

Sphingomyelins (SMs) are bioactive sphingolipids found in mammalian cell membranes.1 SMs make up 2-15% of the total organ phospholipid population but are found at higher concentrations in the brain and myelin sheaths surrounding peripheral nerves. They interact with cholesterol to control its distribution within cellular membranes and maintain cholesterol homeostasis in cells. SMs undergo hydrolysis by sphingomyelinase to form ceramides, which are sphingolipid mediators of intracellular signaling.2 This product contains SM molecular species with primarily C18:0, C24:1, and C22:0 fatty acyl chain lengths. As this product is derived from a natural source, there may be variations in the sphingoid backbone. [Matreya, LLC. Catalog No. 1051]

This information has been provided by Cayman Chemical

References

1. Slotte, J.P., and Ramstedt, B. The functional role of sphingomyelin in cell membranes. Eur. J. Lipid Sci. Technol. 109(10), 977-981 (2007).

Reactions

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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
Pubmed ID: 20671299

String Representations

InChiKey (Click to copy)
LKQLRGMMMAHREN-YJFXYUILSA-N
InChi (Click to copy)
InChI=1S/C41H83N2O6P/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/h32,34,39-40,44H,6-31,33,35-38H2,1-5H3,(H-,42,45,46,47)/b34-32+/t39-,40+/m0/s1
SMILES (Click to copy)
O(P(=O)(OC[C@]([H])(NC(=O)CCCCCCCCCCCCCCCCC)[C@]([H])(O)/C=C/CCCCCCCCCCCCC)[O-])CC[N+](C)(C)C

Other Databases

HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 50
Rings 0
Aromatic Rings 0
Rotatable Bonds 38
Van der Waals Molecular Volume 807.15
Topological Polar Surface Area 107.92
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 11.99
Molar Refractivity 212.61

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Updated at
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