Structure Database (LMSD)

Common Name
ibho#22
Systematic Name
3R-hydroxy-13-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tridecanoic acid
Synonyms
  • 3R-hydroxy-13-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acid
LM ID
LMFA13040144
Formula
C28H41NO8
Exact Mass
Calculate m/z
519.283219
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)
FUIIPNLIVZGYJM-RHENGWIESA-N
InChi (Click to copy)
InChI=1S/C28H41NO8/c1-19-25(37-27(34)22-18-29-23-14-10-9-13-21(22)23)17-24(31)28(36-19)35-15-11-7-5-3-2-4-6-8-12-20(30)16-26(32)33/h9-10,13-14,18-20,24-25,28-31H,2-8,11-12,15-17H2,1H3,(H,32,33)/t19-,20+,24+,25+,28+/m0/s1
SMILES (Click to copy)
O(CCCCCCCCCC[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
79374
PubChem CID
86289900
SMID ID
ibho#22

Calculated Physicochemical Properties

Heavy Atoms 37
Rings 3
Aromatic Rings 2
Rotatable Bonds 17
Van der Waals Molecular Volume 499.56
Topological Polar Surface Area 140.38
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 6.11
Molar Refractivity 141.21

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