Structure Database (LMSD)

Common Name
Cer(d18:1/18:1(9Z))
Systematic Name
N-(9Z-octadecenoyl)-sphing-4-enine
Synonyms
  • C18:1 Cer
  • N-(9Z-octadecenoyl)-ceramide
  • N-(oleoyl)-ceramide
  • N-oleoyl-sphingosine
  • Cer[NS]
LM ID
LMSP02010003
Formula
Exact Mass
Calculate m/z
563.527744
Sum Composition
Abbrev Chains
Cer 18:1;O2/18:1
Status
Curated




Classification

Biological Context

C18:1 Ceramide is a naturally occurring ceramide.1,2,3 Levels of C18:1 ceramide are elevated in overweight and insulin-resistant mice and cattle.1,2 C18:1 Ceramide is also increased in the plasma and ovarian tissue of patients with advanced ovarian cancer.3

This information has been provided by Cayman Chemical

References

1. Sajan, M.P., Ivey, R.A., Lee, M.C., et al. Hepatic insulin resistance in ob/ob mice involves increases in ceramide, aPKC activity, and selective impairment of Akt-dependent FoxO1 phosphorylation. J. Lipid Res. 56(1), 70-80 (2015).

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

String Representations

InChiKey (Click to copy)
OBFSLMQLPNKVRW-RHPAUOISSA-N
InChi (Click to copy)
InChI=1S/C36H69NO3/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/h17-18,29,31,34-35,38-39H,3-16,19-28,30,32-33H2,1-2H3,(H,37,40)/b18-17-,31-29+/t34-,35+/m0/s1
SMILES (Click to copy)
OC[C@]([H])(NC(=O)CCCCCCC/C=C\CCCCCCCC)[C@]([H])(O)/C=C/CCCCCCCCCCCCC

Other Databases

HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 40
Rings 0
Aromatic Rings 0
Rotatable Bonds 31
Van der Waals Molecular Volume 660.81
Topological Polar Surface Area 69.56
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 3
logP 10.98
Molar Refractivity 176.21

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Updated at
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