Structure Database (LMSD)

Common Name
Cer(d18:1/18:0)
Systematic Name
N-(octadecanoyl)-sphing-4-enine
Synonyms
  • C18 Cer
  • N-(octadecanoyl)-ceramide
  • N-(stearoyl)-ceramide
  • Cer[NS]
LM ID
LMSP02010006
Formula
C36H71NO3
Exact Mass
Calculate m/z
565.543394
Sum Composition
Cer 36:1;O2
Abbrev Chains
Cer 18:1;O2/18:0
Status
Curated
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Classification

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

Biological Context

C18 Ceramide is an endogenous bioactive sphingolipid. It is the primary short-chain ceramide found in brain tissue whose synthesis is regulated by longevity-assurance homologue 1 (Lass1) in mice.1 Increased expression of C18 ceramide reduces cell growth in UM-SCC-22A squamous cell carcinoma cells.2 It is selectively downregulated in 32 human head and neck squamous cell carcinoma tumor tissues as compared to non-squamous tumor tissues. C18 Ceramide concentration is significantly higher in muscle tissue of type 2 diabetic patients compared with non-diabetic patients and is positively correlated to body mass index and inversely related to insulin sensitivity.3 [Matreya, LLC. Catalog No. 1832]

This information has been provided by Cayman Chemical

References

1. Bergman, B.C., Brozinick, J.T., Strauss, A., et al. Muscle sphingolipids during rest and exercise: A C18:0 signature for insulin resistance in humans. Diabetologia 59(3), 785-791 (2016).
2. Mizutani, Y., Kihara, A., and Igarashi, Y. Mammalian Lass6 and its related family members regulate synthesis of specific ceramides. Biochem J. 390(Pt. 1), 263-271 (2005).
3. Koybasi, S., Senkal, C.E., Sundararaj, K., et al. Defects in cell growth regulation by C18:0-ceramide and longevity assurance gene 1 in human head and neck squamous cell carcinomas. J. Biol. Chem. 279(43), 44311-44319 (2004).

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)
VODZWWMEJITOND-NXCSZAMKSA-N
InChi (Click to copy)
InChI=1S/C36H71NO3/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-36(40)37-34(33-38)35(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h29,31,34-35,38-39H,3-28,30,32-33H2,1-2H3,(H,37,40)/b31-29+/t34-,35+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(NC(CCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

Other Databases

HMDB ID
HMDB0004950
CHEBI ID
72961
PubChem CID
5283565
SwissLipids ID
SLM:000000555
Cayman ID
19556
PDB ID
18C

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 0
Aromatic Rings 0
Rotatable Bonds 32
Van der Waals Molecular Volume 663.45
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 11.20
Molar Refractivity 176.30

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Updated at
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