Structure Database (LMSD)

Common Name
glas#18
Systematic Name
1-O-(10R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-undecanoyl)-β-D-glucopyranose
Synonyms
  • beta-D-glucos-1''-yl-10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoate
LM ID
LMFA13040103
Formula
C23H42O11
Exact Mass
Calculate m/z
494.272715
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)
QBDRWZBYGHVNSP-BZNPLBMASA-N
InChi (Click to copy)
InChI=1S/C23H42O11/c1-13(31-22-16(26)11-15(25)14(2)32-22)9-7-5-3-4-6-8-10-18(27)34-23-21(30)20(29)19(28)17(12-24)33-23/h13-17,19-26,28-30H,3-12H2,1-2H3/t13-,14+,15-,16-,17-,19-,20+,21-,22-,23+/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCC(=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
79303
PubChem CID
86289878
SMID ID
glas#18

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 2
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 475.79
Topological Polar Surface Area 179.51
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 11
logP 2.86
Molar Refractivity 123.92

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