Structure Database (LMSD)

Common Name
icas#20
Systematic Name
11R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-dodecanoic acid
Synonyms
  • 11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)- tetrahydropyran-2'-yloxy)-dodecanoic acid
LM ID
LMFA13040118
Formula
C27H39NO7
Exact Mass
Calculate m/z
489.272654
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)
AFPJDDPSVYDRDB-DRONAGRDSA-N
InChi (Click to copy)
InChI=1S/C27H39NO7/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/h10-11,13-14,17-19,23-24,27-29H,3-9,12,15-16H2,1-2H3,(H,30,31)/t18-,19+,23-,24-,27-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCC(=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
78745
PubChem CID
86289643
SMID ID
icas#20

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 2
Rotatable Bonds 15
Van der Waals Molecular Volume 473.47
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 6.46
Molar Refractivity 134.69

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