Structure Database (LMSD)

Common Name
GlcCer(d18:2(4E,8E)/16:0(2OH[R]))
Systematic Name
N-(2R-hydroxyhexadecanoyl)-1-β-glucosyl-4E,8E-octadecasphingadienine
Synonyms
  • 1-O-glucopyranosyl-2-N-2'-hydroxyhexadecanoyl-4E,8E-sphingadienine
LM ID
LMSP05010064
Formula
C40H75NO9
Exact Mass
Calculate m/z
713.544184
Sum Composition
HexCer 34:2;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]

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)
HOMYIYLRRDTKAA-HIMJKWBMSA-N
InChi (Click to copy)
InChI=1S/C40H75NO9/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-33(43)32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)41-39(48)34(44)29-27-25-23-21-18-16-14-12-10-8-6-4-2/h19-20,26,28,32-38,40,42-47H,3-18,21-25,27,29-31H2,1-2H3,(H,41,48)/b20-19+,28-26+/t32-,33+,34+,35+,36+,37-,38+,40+/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)CCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CC/C=C/CCCCCCCCC

Other Databases

CHEBI ID
142276
PubChem CID
134812558

Calculated Physicochemical Properties

Heavy Atoms 50
Rings 1
Aromatic Rings 0
Rotatable Bonds 32
Van der Waals Molecular Volume 770.39
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 8.99
Molar Refractivity 204.56

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Created at
-
Updated at
20th Jul 2021