Structure Database (LMSD)

Common Name
icas#14
Systematic Name
7R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-octanoic acid
Synonyms
  • 7R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)- tetrahydropyran-2'-yloxy)-octanoic acid
LM ID
LMFA13040123
Formula
C23H31NO7
Exact Mass
Calculate m/z
433.210054
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)
WFTLFOBGVIIQCZ-JEFMMDONSA-N
InChi (Click to copy)
InChI=1S/C23H31NO7/c1-14(8-4-3-5-11-21(26)27)29-23-19(25)12-20(15(2)30-23)31-22(28)17-13-24-18-10-7-6-9-16(17)18/h6-7,9-10,13-15,19-20,23-25H,3-5,8,11-12H2,1-2H3,(H,26,27)/t14-,15+,19-,20-,23-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCC(=O)O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

Other Databases

CHEBI ID
79061
PubChem CID
86289743
SMID ID
icas#14

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 3
Aromatic Rings 2
Rotatable Bonds 11
Van der Waals Molecular Volume 404.27
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.90
Molar Refractivity 116.22

Admin

Created at
14th Jun 2020
Updated at
20th Oct 2021