Structure Database (LMSD)

Common Name
ibho#18
Systematic Name
3R-hydroxy-11-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-undecanoic acid
Synonyms
  • 3R-hydroxy-11-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acid
LM ID
LMFA13040142
Formula
C26H37NO8
Exact Mass
Calculate m/z
491.251919
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)
KNUQGRSJUADXIR-SIHSWOPCSA-N
InChi (Click to copy)
InChI=1S/C26H37NO8/c1-17-23(35-25(32)20-16-27-21-12-8-7-11-19(20)21)15-22(29)26(34-17)33-13-9-5-3-2-4-6-10-18(28)14-24(30)31/h7-8,11-12,16-18,22-23,26-29H,2-6,9-10,13-15H2,1H3,(H,30,31)/t17-,18+,22+,23+,26+/m0/s1
SMILES (Click to copy)
O(CCCCCCCC[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
79372
PubChem CID
86289898
SMID ID
ibho#18

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 3
Aromatic Rings 2
Rotatable Bonds 15
Van der Waals Molecular Volume 464.96
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 5.33
Molar Refractivity 131.97

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