Structure Database (LMSD)

OH OH OH OH O OH O N H OH O
Common Name
Chrysogeside A
Systematic Name
N-(2R-hydroxy-3E-octadecenoyl)-1-β-D-glucopyranosyl-hexadecasphing-4E,8Z-dienine
Synonyms
LM ID
LMSP05010096
Formula
C40H73NO9
Exact Mass
Calculate m/z
711.528534
Sum Composition
HexCer 34:3;O3
Abbrev Chains
GlcCer 16:2;O2/18:1;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)
ZSSGCZVAMMVAPO-CTUXNYLFSA-N
InChi (Click to copy)
InChI=1S/C40H73NO9/c1-3-5-7-9-11-13-15-16-17-19-21-23-25-27-29-34(44)39(48)41-32(31-49-40-38(47)37(46)36(45)35(30-42)50-40)33(43)28-26-24-22-20-18-14-12-10-8-6-4-2/h18,20,26-29,32-38,40,42-47H,3-17,19,21-25,30-31H2,1-2H3,(H,41,48)/b20-18-,28-26+,29-27+/t32-,33+,34+,35+,36+,37-,38+,40+/m0/s1
SMILES (Click to copy)
C([C@H](NC([C@H](O)/C=C/CCCCCCCCCCCCCC)=O)[C@H](O)/C=C/CC/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
Penicillium chrysogenum (#5076)
Eurotiomycetes (#147545)
Cerebrosides and 2-pyridone alkaloids from the halotolerant fungus Penicillium chrysogenum grown in a hypersaline medium.,
J Nat Prod, 2011
Pubmed ID: 21381678

Other Databases

CHEBI ID
68069
PubChem CID
53355808

Calculated Physicochemical Properties

Heavy Atoms 50
Rings 1
Aromatic Rings 0
Rotatable Bonds 31
Van der Waals Molecular Volume 767.75
Topological Polar Surface Area 171.01
Hydrogen Bond Donors 7
Hydrogen Bond Acceptors 10
logP 8.77
Molar Refractivity 204.46

Admin

Created at
18th May 2020
Updated at
2nd Feb 2021