Structure Database (LMSD)

Common Name
ibho#26
Systematic Name
3R-hydroxy-15-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-pentadecanoic acid
Synonyms
  • 3R-hydroxy-15-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acid
LM ID
LMFA13040146
Formula
C30H45NO8
Exact Mass
Calculate m/z
547.314519
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty acyl glycosides [FA13]
Ascarosides [FA1304]

String Representations

InChiKey (Click to copy)
HVABDZVINXGTFF-PSEFKOPQSA-N
InChi (Click to copy)
InChI=1S/C30H45NO8/c1-21-27(39-29(36)24-20-31-25-16-12-11-15-23(24)25)19-26(33)30(38-21)37-17-13-9-7-5-3-2-4-6-8-10-14-22(32)18-28(34)35/h11-12,15-16,20-22,26-27,30-33H,2-10,13-14,17-19H2,1H3,(H,34,35)/t21-,22+,26+,27+,30+/m0/s1
SMILES (Click to copy)
O(CCCCCCCCCCCC[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

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

Other Databases

CHEBI ID
79376
PubChem CID
86289902
SMID ID
ibho#26

Calculated Physicochemical Properties

Heavy Atoms 39
Rings 3
Aromatic Rings 2
Rotatable Bonds 19
Van der Waals Molecular Volume 534.16
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 6.89
Molar Refractivity 150.44

Admin

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