Structure Database (LMSD)

Common Name
Cer(d18:1(8E)/16:0(2OH[R]))
Systematic Name
N-(2R-hydroxyhexadecanoyl)-8E-octadecasphingenine
Synonyms
  • N-(1,3-dihydroxyoctadec-8-en-2-yl)-2-hydroxyhexadecanamide
LM ID
LMSP02010099
Formula
C34H67NO4
Exact Mass
Calculate m/z
553.507009
Sum Composition
Cer 34:1;O3
Abbrev Chains
Cer 18:1;O2/16:0;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

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

Reactions

Filter by species:
ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
Click on an edge to display the reaction(s).
Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Avena abyssinica (#146529)
Magnoliopsida (#3398)
Potential application of oat-derived ceramides in improving skin barrier function: Part 1. Isolation and structural characterization.,
J Chromatogr B Analyt Technol Biomed Life Sci, 2017
Pubmed ID: 28950193

String Representations

InChiKey (Click to copy)
YHEYVZJWYNYBFN-BNSIVLFQSA-N
InChi (Click to copy)
InChI=1S/C34H67NO4/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-32(37)31(30-36)35-34(39)33(38)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,31-33,36-38H,3-18,21-30H2,1-2H3,(H,35,39)/b20-19+/t31-,32+,33+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(NC([C@H](O)CCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCC/C=C/CCCCCCCCC

Other Databases

CHEBI ID
183016
PubChem CID
15104949

Calculated Physicochemical Properties

Heavy Atoms 39
Rings 0
Aromatic Rings 0
Rotatable Bonds 30
Van der Waals Molecular Volume 637.64
Topological Polar Surface Area 89.79
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 9.68
Molar Refractivity 168.97

Admin

Created at
-
Updated at
18th Mar 2021