LIPID MAPS

Structure Database (LMSD)

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Common Name

SM(d18:0/16:0)

Systematic Name

N-(hexadecanoyl)-sphinganine-1-phosphocholine

Synonyms

C16DH Sphingomyelin
C16 dihydrosphingomyelin

LM ID

LMSP03010004

Formula

C₃₉H₈₁N₂O₆P

Exact Mass

Calculate m/z

704.583224

Sum Composition

SM 34:0;O2

Abbrev Chains

SM 18:0;O2/16:0

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

C16 Dihydrosphingomyelin is a sphingolipid and saturated form of C16 sphingomyelin. It is the most abundant phospholipid in the human lens and redistributes to the barrier region with increasing age, and serum levels of C16 dihydrosphingomyelin are decreased in patients with chronic migraine.^1,2 C16 Dihydrosphingomyelin has been used as a helper lipid in the generation of liposomal lipid nanoparticles (LNPs) for the delivery of mRNA in vitro and in vivo.³ Incorporation of C16 dihydrosphingomyelin into liposomal LNPs increases blood circulation half-life and improves extrahepatic distribution and transfection in mice compared with liposomal LNPs containing egg sphingomyelin.

This information has been provided by Cayman Chemical

References

1. Deeley, J.M., Hankin, J.A., Friedrich, M.G., et al. Sphingolipid distribution changes with age in the human lens. J. Lipid Res. 51(9), 2753-2760 (2010).

2. Ouro, A., Castro-Mosquera, M., Rodríguez-Arrizabalaga, M., et al. Elevated serum levels of acid sphingomyelinase in female patients with episodic and chronic migraine. Antioxidants (Basel) 14(2), 159 (2025).

3. Liao, S., Fox, K., Birkenshaw, A., et al. Liposomal lipid nanoparticles containing dihydrosphingomyelin exhibit improved stability and extended hepatic and extrahepatic transfection. J. Control Release 396, 115098 (2026).

Reactions

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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

DOI: 10.1194/jlr.M009449

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

QHZIGNLCLJPLCU-QPPIDDCLSA-N

InChi (Click to copy)

InChI=1S/C39H81N2O6P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-38(42)37(36-47-48(44,45)46-35-34-41(3,4)5)40-39(43)33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h37-38,42H,6-36H2,1-5H3,(H-,40,43,44,45)/t37-,38+/m0/s1

SMILES (Click to copy)

[C@](COP(=O)([O-])OCC[N+](C)(C)C)([H])(NC(CCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCCCCCCCCCCCCC