Structure Database (LMSD)
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
Exact Mass
Calculate m/z
781.606784
Sum Composition
Abbrev Chains
GlcCer 19:3;O2/20:0;O
Status
Active
No other lipid differing only in stereochemistry/bond geometry found
3D model of Ophidiacerebroside A
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Main
Classification
Category
Main Class
Sub Class
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
J Org Chem, 1994
DOI:
10.1021/jo00080a023
Other Databases
PubChem CID
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
Admin
Created at
13th Jul 2021
Updated at
13th Jul 2021