Structure Database (LMSD)

Common Name
glas#22
Systematic Name
1-O-(12R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tridecanoyl)-β-D-glucopyranose
Synonyms
  • beta-D-glucos-1''-yl-12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoate
LM ID
LMFA13040100
Formula
C25H46O11
Exact Mass
Calculate m/z
522.304016
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)
GPSYFHFACFTZSX-NGGGFPBGSA-N
InChi (Click to copy)
InChI=1S/C25H46O11/c1-15(33-24-18(28)13-17(27)16(2)34-24)11-9-7-5-3-4-6-8-10-12-20(29)36-25-23(32)22(31)21(30)19(14-26)35-25/h15-19,21-28,30-32H,3-14H2,1-2H3/t15-,16+,17-,18-,19-,21-,22+,23-,24-,25+/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCC(=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
79305
PubChem CID
86289880
SMID ID
glas#22

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 2
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 510.39
Topological Polar Surface Area 179.51
Hydrogen Bond Donors 6
Hydrogen Bond Acceptors 11
logP 3.64
Molar Refractivity 133.15

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