Structure Database (LMSD)

Common Name
Cer(d18:1/16:0)
Systematic Name
N-(hexadecanoyl)-sphing-4-enine
Synonyms
  • C16 Cer
  • N-(hexadecanoyl)-ceramide
  • N-(palmitoyl)-ceramide
  • N-palmitoyl-sphingosine
  • Cer[NS]
LM ID
LMSP02010004
Formula
C34H67NO3
Exact Mass
Calculate m/z
537.512094
Sum Composition
Cer 34:1;O2
Abbrev Chains
Cer 18:1;O2/16:0
Status
Curated
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Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Ceramides [SP02]
N-acylsphingosines (ceramides) [SP0201]

Biological Context

C16 Ceramide is a sphingolipid. It incorporates into the mitochondrial outer membrane and forms channels that increase its permeability.1 C16 Ceramide levels are increased by PPMP or MAPP in isolated human neutrophils and are correlated with an increase in apoptosis.2 It accumulates in the lungs of patients with cystic fibrosis compared with the lungs of patients with pulmonary hypertension.3 Plasma levels of C16 ceramide are also increased in patients with acute coronary syndrome, and an increased plasma ratio of C16 to C24:0 ceramide is associated with major adverse cardiac events.4 It is also increased in tumor tissue from patients with breast cancer and is associated with metastatic cancer.5

This information has been provided by Cayman Chemical

References

1. Seumois, G., Fillet, M., Gillet, L., et al. De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis. J. Leukoc. Biol. 81(6), 1477-1486 (2007).
2. Siskind, L.J., Kolesnick, R.N., and Colombini, M. Ceramide forms channels in mitochondrial outer membranes at physiologically relevant concentrations. Mitochondrion 6(3), 118-125 (2006).
3. Brodlie, M., McKean, M.C., Johnson, G.E., et al. Ceramide is increased in the lower airway epithelium of people with advanced cystic fibrosis lung disease. Am. J. Respir. Crit. Care Med. 182(3), 369-375 (2010).
4. Anroedh, S., Hilvo, M., Akkerhuis, K.M., et al. Plasma concentrations of molecular lipid species predict long-term clinical outcome in coronary artery disease patients. J. Lipid Res. 59(9), 1729-1737 (2018).
5. Schiffmann, S., Sandner, J., Birod, K., et al. Ceramide synthases and ceramide levels are increased in breast cancer tissue. Carcinogenesis 30(5), 745-752 (2009).

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
Mus musculus (#10090)
Mammalia (#40674)
Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010
Pubmed ID: 20574076

String Representations

InChiKey (Click to copy)
YDNKGFDKKRUKPY-TURZORIXSA-N
InChi (Click to copy)
InChI=1S/C34H67NO3/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-33(37)32(31-36)35-34(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h27,29,32-33,36-37H,3-26,28,30-31H2,1-2H3,(H,35,38)/b29-27+/t32-,33+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(NC(CCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

Other Databases

HMDB ID
HMDB0004949
CHEBI ID
72959
PubChem CID
5283564
SwissLipids ID
SLM:000000554
Cayman ID
10681
PDB ID
16C

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 0
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 628.85
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 10.42
Molar Refractivity 167.07

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Updated at
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