Structure Database (LMSD)

Common Name
glas#3
Systematic Name
1-O-(8R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-nonenoyl)-β-D-glucopyranose
Synonyms
  • beta-D-glucos-1''-yl-8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoate
LM ID
LMFA13040105
Formula
C21H36O11
Exact Mass
Calculate m/z
464.225765
Status
Active
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)
USHOVWZTBFBUPQ-AHQKKNCYSA-N
InChi (Click to copy)
InChI=1S/C21H36O11/c1-11(29-20-14(24)9-13(23)12(2)30-20)7-5-3-4-6-8-16(25)32-21-19(28)18(27)17(26)15(10-22)31-21/h6,8,11-15,17-24,26-28H,3-5,7,9-10H2,1-2H3/b8-6+/t11-,12+,13-,14-,15-,17-,18+,19-,20-,21+/m1/s1
SMILES (Click to copy)
O([C@@H](CCCC/C=C/C(=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
79300
PubChem CID
86289875
SMID ID
glas#3

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 2
Aromatic Rings 0
Rotatable Bonds 11
Van der Waals Molecular Volume 438.55
Topological Polar Surface Area 179.51
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 11
logP 1.86
Molar Refractivity 114.59

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