Structure Database (LMSD)

Common Name
icos#15
Systematic Name
10-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-decenoic acid
Synonyms
  • 10-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic acid
LM ID
LMFA13040135
Formula
C25H33NO7
Exact Mass
Calculate m/z
459.225704
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)
SCZSSSOEHFCMKR-ONIXZVGUSA-N
InChi (Click to copy)
InChI=1S/C25H33NO7/c1-17-22(33-24(30)19-16-26-20-12-9-8-11-18(19)20)15-21(27)25(32-17)31-14-10-6-4-2-3-5-7-13-23(28)29/h7-9,11-13,16-17,21-22,25-27H,2-6,10,14-15H2,1H3,(H,28,29)/b13-7+/t17-,21+,22+,25+/m0/s1
SMILES (Click to copy)
O(CCCCCCC/C=C/C(=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
79118
PubChem CID
86289761
SMID ID
icos#15

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 2
Rotatable Bonds 13
Van der Waals Molecular Volume 436.23
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 5.46
Molar Refractivity 125.36

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