Structure Database (LMSD)

OH OH OH OH O OH H NH O O OH H
Common Name
GlcCer(d18:2(4E,8Z)/25:0(2OH[R]))
Systematic Name
N-(2R-hydroxypentacosanoyl)-1-β-glucosyl-4E,8Z-octadecasphingadienine
Synonyms
  • 1-O-glucopyranosyl-2-N-2'-hydroxypentacosanoyl-4,8-sphingadienine
LM ID
LMSP05010057
Formula
C49H93NO9
Exact Mass
Calculate m/z
839.685034
Sum Composition
HexCer 43:2;O3
Abbrev Chains
GlcCer 18:2;O2/25:0;O
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

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

String Representations

InChiKey (Click to copy)
WAMFEJVCOLBTNW-GNFPIGOISA-N
InChi (Click to copy)
InChI=1S/C49H93NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-26-28-30-32-34-36-38-43(53)48(57)50-41(40-58-49-47(56)46(55)45(54)44(39-51)59-49)42(52)37-35-33-31-29-27-25-16-14-12-10-8-6-4-2/h27,29,35,37,41-47,49,51-56H,3-26,28,30-34,36,38-40H2,1-2H3,(H,50,57)/b29-27-,37-35+/t41-,42+,43+,44+,45+,46-,47+,49+/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)CCCCCCCCCCCCCCCCCCCCCCC)=O)[C@]([H])(O)/C=C/CC/C=C\CCCCCCCCC

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Secale cereale (#4550)
Magnoliopsida (#3398)
Analysis of Glucocerebrosides of Rye (Secale cereale L. cv Puma) Leaf and Plasma Membrane.,
Plant Physiol, 1991
Pubmed ID: 16667981

Other Databases

PubChem CID
134812551

Calculated Physicochemical Properties

Heavy Atoms 59
Rings 1
Aromatic Rings 0
Rotatable Bonds 41
Van der Waals Molecular Volume 926.09
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 12.51
Molar Refractivity 246.11

Admin

Created at
-
Updated at
24th Mar 2021