Structure Database (LMSD)

Common Name
ibha#10
Systematic Name
3R-hydroxy-8R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-nonanoic acid
Synonyms
  • 3R-hydroxy-8R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acid
LM ID
LMFA13040115
Formula
C24H33NO8
Exact Mass
Calculate m/z
463.220619
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)
RHSYRFCZUCKPGK-JIJTWFEJSA-N
InChi (Click to copy)
InChI=1S/C24H33NO8/c1-14(7-3-4-8-16(26)11-22(28)29)31-24-20(27)12-21(15(2)32-24)33-23(30)18-13-25-19-10-6-5-9-17(18)19/h5-6,9-10,13-16,20-21,24-27H,3-4,7-8,11-12H2,1-2H3,(H,28,29)/t14-,15+,16+,20-,21-,24-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCC[C@H](O)CC(=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
79334
PubChem CID
86289887
SMID ID
ibha#10

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 2
Rotatable Bonds 12
Van der Waals Molecular Volume 430.36
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 4.55
Molar Refractivity 122.74

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Created at
14th Jun 2020
Updated at
14th Jun 2020