Structure Database (LMSD)

OH OH OH OH OH O O N H OH O
Common Name
Ophidiacerebroside A
Systematic Name
N-(2R-hydroxy-eicosanoyl)-1-β-D-glucosyl-9-methyl-sphing-4E,8E,10E-trienine
Synonyms
LM ID
LMSP05010170
Formula
C45H83NO9
Exact Mass
Calculate m/z
781.606784
Sum Composition
HexCer 39:3;O3
Abbrev Chains
GlcCer 19:3;O2/20:0;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)
HXERECODZWDGTP-AWAJSSJXSA-N
InChi (Click to copy)
InChI=1S/C45H83NO9/c1-4-6-8-10-12-13-14-15-16-17-18-19-20-22-24-28-33-39(49)44(53)46-37(35-54-45-43(52)42(51)41(50)40(34-47)55-45)38(48)32-29-25-27-31-36(3)30-26-23-21-11-9-7-5-2/h26,29-32,37-43,45,47-52H,4-25,27-28,33-35H2,1-3H3,(H,46,53)/b30-26+,32-29+,36-31+/t37-,38+,39+,40+,41+,42-,43+,45+/m0/s1
SMILES (Click to copy)
C([C@H](NC([C@H](O)CCCCCCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CC/C=C(\C)/C=C/CCCCCCC)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Ophidiaster ophidianus (#232926)
Asteroidea (#7588)
Ophidiacerebrosides: cytotoxic glycosphingolipids containing a novel sphingosine from a sea star,
J Org Chem, 1994

Other Databases

PubChem CID
10440246

Calculated Physicochemical Properties

Heavy Atoms 55
Rings 1
Aromatic Rings
Rotatable Bonds 35
Van der Waals Molecular Volume 854.25
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 10.72
Molar Refractivity 227.55

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