LIPID MAPS

Structure Database (LMSD)

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Common Name

SM(d18:1/12:0)

Systematic Name

N-(dodecanoyl)-sphing-4-enine-1-phosphocholine

Synonyms

N-lauroyl-D-erythro-Sphingosylphosphoryl choline

LM ID

LMSP03010002

Formula

C₃₅H₇₁N₂O₆P

Exact Mass

Calculate m/z

646.504974

Sum Composition

SM 30:1;O2

Abbrev Chains

SM 18:1;O2/12:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

View spectra on the LIPID MAPS® Standards Spectra Database

Classification

Biological Context

C12 Sphingomyelin is a sphingolipid. It increases IL-1α, IL-6, and TNF-α levels in RAW 264.7 cells, mouse bone marrow-derived macrophages (BMDMs), and mouse bone marrow-derived dendritic cells (BMDCs) and induces pyroptosis in RAW 264.7 macrophages and mouse BMDMs but not mouse BMDCs.¹ It activates NF-κB signaling in a reporter assay in LPS-stimulated cells expressing mouse or human toll-like receptor 4 (TLR4) and myeloid differentiation 2 (MD-2).

This information has been provided by Cayman Chemical

References

1. Huang, X., Kanoh, H., Ueno, J., et al. Modulation function of sphingomyelin molecular species in TLR4 signaling and cell death. Cell Rep. 44(12), 116568 (2025).

Reactions

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String Representations

InChiKey (Click to copy)

HZCLJRFPXMKWHR-FEBLJDHQSA-N

InChi (Click to copy)

InChI=1S/C35H71N2O6P/c1-6-8-10-12-14-16-17-18-19-21-22-24-26-28-34(38)33(32-43-44(40,41)42-31-30-37(3,4)5)36-35(39)29-27-25-23-20-15-13-11-9-7-2/h26,28,33-34,38H,6-25,27,29-32H2,1-5H3,(H-,36,39,40,41)/b28-26+/t33-,34+/m0/s1

SMILES (Click to copy)

O(P(=O)(OC[C@]([H])(NC(=O)CCCCCCCCCCC)[C@]([H])(O)/C=C/CCCCCCCCCCCCC)[O-])CC[N+](C)(C)C