Structure Database (LMSD)

Common Name
ibho#16
Systematic Name
3R-hydroxy-10-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-decanoic acid
Synonyms
  • 3R-hydroxy-10-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acid
LM ID
LMFA13040141
Formula
C25H35NO8
Exact Mass
Calculate m/z
477.236269
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)
IHRBCDQOWOHXDO-CGHZYJDXSA-N
InChi (Click to copy)
InChI=1S/C25H35NO8/c1-16-22(34-24(31)19-15-26-20-11-7-6-10-18(19)20)14-21(28)25(33-16)32-12-8-4-2-3-5-9-17(27)13-23(29)30/h6-7,10-11,15-17,21-22,25-28H,2-5,8-9,12-14H2,1H3,(H,29,30)/t16-,17+,21+,22+,25+/m0/s1
SMILES (Click to copy)
O(CCCCCCC[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
79371
PubChem CID
86289897
SMID ID
ibho#16

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 3
Aromatic Rings 2
Rotatable Bonds 14
Van der Waals Molecular Volume 447.66
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 4.94
Molar Refractivity 127.36

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