Structure Database (LMSD)

Common Name
glas#26
Systematic Name
1-O-(14R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-pentadecanoyl)-β-D-glucopyranose
Synonyms
  • beta-D-glucos-1''-yl-14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoate
LM ID
LMFA13040098
Formula
C27H50O11
Exact Mass
Calculate m/z
550.335315
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty acyl glycosides [FA13]
Ascarosides [FA1304]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Caenorhabditis elegans (#6239)
Chromadorea (#119089)
Comparative Metabolomics Reveals Biogenesis of Ascarosides, a Modular Library of Small-Molecule Signals in C. elegans,
J Am Chem Soc, 2012
Pubmed ID: 22239548

String Representations

InChiKey (Click to copy)
GSRDQXYUFNVAAO-SEYCSDJLSA-N
InChi (Click to copy)
InChI=1S/C27H50O11/c1-17(35-26-20(30)15-19(29)18(2)36-26)13-11-9-7-5-3-4-6-8-10-12-14-22(31)38-27-25(34)24(33)23(32)21(16-28)37-27/h17-21,23-30,32-34H,3-16H2,1-2H3/t17-,18+,19-,20-,21-,23-,24+,25-,26-,27+/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCCC(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
79307
PubChem CID
86289882
SMID ID
glas#26

Calculated Physicochemical Properties

Heavy Atoms 38
Rings 2
Aromatic Rings 0
Rotatable Bonds 18
Van der Waals Molecular Volume 544.99
Topological Polar Surface Area 179.51
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 11
logP 4.42
Molar Refractivity 142.39

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Created at
13th Jun 2020
Updated at
13th Jun 2020