Structure Database (LMSD)

Common Name
Cer(d18:1(8Z)/20:0(2OH[R]))
Systematic Name
N-(2R-hydroxyicosanoyl)-8Z-octadecasphingenine
Synonyms
  • N-(1,3-dihydroxyoctadec-8-en-2-yl)-2-hydroxyicosanamide
LM ID
LMSP020101001
Formula
C38H75NO4
Exact Mass
Calculate m/z
609.569609
Sum Composition
Cer 38:1;O3
Abbrev Chains
Cer 18:1;O2/20:0;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)
BFOBXWUPPFTLDM-QKQLTUQRSA-N
InChi (Click to copy)
InChI=1S/C38H75NO4/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-33-37(42)38(43)39-35(34-40)36(41)32-30-28-26-24-22-20-16-14-12-10-8-6-4-2/h22,24,35-37,40-42H,3-21,23,25-34H2,1-2H3,(H,39,43)/b24-22-/t35-,36+,37+/m0/s1
SMILES (Click to copy)
[C@](CO)([H])(NC([C@H](O)CCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCC/C=C\CCCCCCCCC

Other Databases

PubChem CID
134812528

Calculated Physicochemical Properties

Heavy Atoms 43
Rings
Aromatic Rings
Rotatable Bonds 34
Van der Waals Molecular Volume 706.84
Topological Polar Surface Area 89.79
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 11.24
Molar Refractivity 187.44

Admin

Created at
-
Updated at
18th Mar 2021