Structure Database (LMSD)

Common Name
Oreacerebroside C
Systematic Name
N-(2R-hydroxy-tetracosanoyl)-1-β-D-glucosyl-sphing-4E,8E,10E-trienine
Synonyms
  • Renieroside A5
LM ID
LMSP05010161
Formula
C48H89NO9
Exact Mass
Calculate m/z
823.653734
Sum Composition
HexCer 42:3;O3
Abbrev Chains
GlcCer 18:3;O2/24:0;O
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
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)
DQZBHYFTNIRPFM-ZXRQIZJTSA-N
InChi (Click to copy)
InChI=1S/C48H89NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-25-27-29-31-33-35-37-42(52)47(56)49-40(39-57-48-46(55)45(54)44(53)43(38-50)58-48)41(51)36-34-32-30-28-26-24-16-14-12-10-8-6-4-2/h16,24,26,28,34,36,40-46,48,50-55H,3-15,17-23,25,27,29-33,35,37-39H2,1-2H3,(H,49,56)/b24-16+,28-26+,36-34+/t40-,41+,42+,43+,44+,45-,46+,48+/m0/s1
SMILES (Click to copy)
C([C@H](NC([C@H](O)CCCCCCCCCCCCCCCCCCCCCC)=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
23643325

Calculated Physicochemical Properties

Heavy Atoms 58
Rings 1
Aromatic Rings 0
Rotatable Bonds 39
Van der Waals Molecular Volume 906.15
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 11.89
Molar Refractivity 241.40

Admin

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