Structure Database (LMSD)

OH OH HO OH OH O OH H NH O O OH H
Common Name
GlcCer(t18:1(8Z)/16:0(2OH[S]))
Systematic Name
N-(2R-hydroxyhexadecanoyl)-1-β-glucosyl-4R-hydroxy-8Z-octadecasphingenine
Synonyms
  • 1-O-glucopyranosyl-2-N-2'-hydroxyhexadecanoyl-4-hydroxy-8-sphingenine
LM ID
LMSP05010042
Formula
C40H77NO10
Exact Mass
Calculate m/z
731.554749
Sum Composition
HexCer 34:1;O4
Abbrev Chains
GlcCer 18:1;O3/16:0;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)
AYBHLNMQTQBJBX-HYAPPWSWSA-N
InChi (Click to copy)
InChI=1S/C40H77NO10/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-32(43)35(45)31(30-50-40-38(48)37(47)36(46)34(29-42)51-40)41-39(49)33(44)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h19,21,31-38,40,42-48H,3-18,20,22-30H2,1-2H3,(H,41,49)/b21-19-/t31-,32+,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@@H](CCC/C=C\CCCCCCCCC)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Phytolacca (#3526)
Magnoliopsida (#3398)
Cyclooxygenase-2 inhibitory cerebrosides from phytolaccae radix.,
Chem Pharm Bull (Tokyo), 2001
Pubmed ID: 11253924

Other Databases

PubChem CID
11227946

Calculated Physicochemical Properties

Heavy Atoms 51
Rings 1
Aromatic Rings 0
Rotatable Bonds 33
Van der Waals Molecular Volume 781.82
Topological Polar Surface Area 191.24
Hydrogen Bond Donors 8
Hydrogen Bond Acceptors 11
logP 8.48
Molar Refractivity 206.55

Admin

Created at
-
Updated at
11th Sep 2021