Structure Database (LMSD)

Common Name
icas#19
Systematic Name
11R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-dodecenoic acid
Synonyms
  • 11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)- tetrahydropyran-2'-yloxy)-2E-dodecenoic acid
LM ID
LMFA13040117
Formula
C27H37NO7
Exact Mass
Calculate m/z
487.257004
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)
CQSBSCBIGYDANS-OQGVURBQSA-N
InChi (Click to copy)
InChI=1S/C27H37NO7/c1-18(12-8-6-4-3-5-7-9-15-25(30)31)33-27-23(29)16-24(19(2)34-27)35-26(32)21-17-28-22-14-11-10-13-20(21)22/h9-11,13-15,17-19,23-24,27-29H,3-8,12,16H2,1-2H3,(H,30,31)/b15-9+/t18-,19+,23-,24-,27-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCC/C=C/C(=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
79106
PubChem CID
86289754
SMID ID
icas#19

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 2
Rotatable Bonds 14
Van der Waals Molecular Volume 470.83
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 6.24
Molar Refractivity 134.59

Admin

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