Structure Database (LMSD)

Common Name
ibho#10
Systematic Name
3R-hydroxy-9-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-nonanoic acid
Synonyms
  • 3R-hydroxy-9-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acid
LM ID
LMFA13040140
Formula
C24H33NO8
Exact Mass
Calculate m/z
463.220619
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)
HYGXRAVBIUWTNN-HIYLOANVSA-N
InChi (Click to copy)
InChI=1S/C24H33NO8/c1-15-21(33-23(30)18-14-25-19-10-6-5-9-17(18)19)13-20(27)24(32-15)31-11-7-3-2-4-8-16(26)12-22(28)29/h5-6,9-10,14-16,20-21,24-27H,2-4,7-8,11-13H2,1H3,(H,28,29)/t15-,16+,20+,21+,24+/m0/s1
SMILES (Click to copy)
O(CCCCCC[C@@H](O)CC(=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
79370
PubChem CID
86289896
SMID ID
ibho#10

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 2
Rotatable Bonds 13
Van der Waals Molecular Volume 430.36
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 4.55
Molar Refractivity 122.74

Admin

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