Structure Database (LMSD)

Common Name
icos#3
Systematic Name
9-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-nonenoic acid
Synonyms
  • 9-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acid
LM ID
LMFA13040138
Formula
C24H31NO7
Exact Mass
Calculate m/z
445.210054
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)
XQKLJTSTLMVZHF-HCCOWPQCSA-N
InChi (Click to copy)
InChI=1S/C24H31NO7/c1-16-21(32-23(29)18-15-25-19-11-8-7-10-17(18)19)14-20(26)24(31-16)30-13-9-5-3-2-4-6-12-22(27)28/h6-8,10-12,15-16,20-21,24-26H,2-5,9,13-14H2,1H3,(H,27,28)/b12-6+/t16-,20+,21+,24+/m0/s1
SMILES (Click to copy)
O(CCCCCC/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
79114
PubChem CID
86289758
SMID ID
icos#3

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 2
Rotatable Bonds 12
Van der Waals Molecular Volume 418.93
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 5.07
Molar Refractivity 120.74

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