Structure Database (LMSD)

Common Name
GlcCer(d18:1(8E)/18:0(2OH[R]))
Systematic Name
N-(2R-hydroxyoctadecanoyl)-1-β-glucosyl-8E-octadecasphingenine
Synonyms
  • 1-O-glucopyranosyl-2-N-2'-hydroxyoctadecanoyl-8E-sphingenine
LM ID
LMSP05010060
Formula
C42H81NO9
Exact Mass
Calculate m/z
743.591134
Sum Composition
HexCer 36:1;O3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sphingolipids [SP]
Neutral glycosphingolipids [SP05]
Simple Glc series [SP0501]

Reactions

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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)
RAYFBAALDWZZOU-ZOIUTUCISA-N
InChi (Click to copy)
InChI=1S/C42H81NO9/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-36(46)41(50)43-34(33-51-42-40(49)39(48)38(47)37(32-44)52-42)35(45)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h20,22,34-40,42,44-49H,3-19,21,23-33H2,1-2H3,(H,43,50)/b22-20+/t34-,35+,36+,37+,38+,39-,40+,42+/m0/s1
SMILES (Click to copy)
[C@](CO[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)([H])(NC([C@H](O)CCCCCCCCCCCCCCCC)=O)[C@]([H])(O)CCCC/C=C/CCCCCCCCC

Other Databases

CHEBI ID
189689
PubChem CID
134812554

Calculated Physicochemical Properties

Heavy Atoms 52
Rings 1
Aromatic Rings 0
Rotatable Bonds 35
Van der Waals Molecular Volume 807.63
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 10.00
Molar Refractivity 213.89

Admin

Created at
-
Updated at
20th Jul 2021