Structure Database (LMSD)

Common Name
icos#18
Systematic Name
11-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-undecanoic acid
Synonyms
  • 11-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acid
LM ID
LMFA13040133
Formula
C26H37NO7
Exact Mass
Calculate m/z
475.257004
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)
XUHBKQAFWINXBW-BXAZGIKQSA-N
InChi (Click to copy)
InChI=1S/C26H37NO7/c1-18-23(34-25(31)20-17-27-21-13-10-9-12-19(20)21)16-22(28)26(33-18)32-15-11-7-5-3-2-4-6-8-14-24(29)30/h9-10,12-13,17-18,22-23,26-28H,2-8,11,14-16H2,1H3,(H,29,30)/t18-,22+,23+,26+/m0/s1
SMILES (Click to copy)
O(CCCCCCCCCCC(=O)O)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

Other Databases

CHEBI ID
79124
PubChem CID
86289765
SMID ID
icos#18

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 3
Aromatic Rings 2
Rotatable Bonds 15
Van der Waals Molecular Volume 456.17
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 6.07
Molar Refractivity 130.07

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Created at
15th Jun 2020
Updated at
15th Jun 2020