Structure Database (LMSD)

Common Name
Oreacerebroside A
Systematic Name
N-(2R-hydroxy-docosanoyl)-1-β-D-glucosyl-sphing-4E,8E,10E-trienine
Synonyms
  • Renieroside A4
LM ID
LMSP05010157
Formula
C46H85NO9
Exact Mass
Calculate m/z
795.622434
Sum Composition
HexCer 40:3;O3
Abbrev Chains
GlcCer 18:3;O2/22:0;O
Status
Active
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
Oreaster reticulatus (#46529)
Asteroidea (#7588)
Oreacerebrosides: Bioactive Cerebrosides with a Triunsaturated Sphingoid Basefrom the Sea Star Oreaster reticulatus,
Eur. J. Org. Chem, 2007
unclassified Haliclona (#2600287)
Demospongiae (#6042)
Renierosides, cerebrosides from a marine sponge Haliclona (Reniera) sp.,
J Nat Prod, 2007
Pubmed ID: 17848089

String Representations

InChiKey (Click to copy)
XESDOPMJHRNWTH-KEJMQFMQSA-N
InChi (Click to copy)
InChI=1S/C46H85NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-23-25-27-29-31-33-35-40(50)45(54)47-38(37-55-46-44(53)43(52)42(51)41(36-48)56-46)39(49)34-32-30-28-26-24-22-16-14-12-10-8-6-4-2/h16,22,24,26,32,34,38-44,46,48-53H,3-15,17-21,23,25,27-31,33,35-37H2,1-2H3,(H,47,54)/b22-16+,26-24+,34-32+/t38-,39+,40+,41+,42+,43-,44+,46+/m0/s1
SMILES (Click to copy)
C([C@H](NC([C@H](O)CCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CC/C=C/C=C/CCCCCCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1

Other Databases

PubChem CID
23643540

Calculated Physicochemical Properties

Heavy Atoms 56
Rings 1
Aromatic Rings
Rotatable Bonds 37
Van der Waals Molecular Volume 871.55
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 11.11
Molar Refractivity 232.17

Admin

Created at
13th Jul 2021
Updated at
13th Jul 2021