Structure Database (LMSD)

Common Name
icas#22
Systematic Name
12R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tridecanoic acid
Synonyms
  • 12R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acid
LM ID
LMFA13040116
Formula
C28H41NO7
Exact Mass
Calculate m/z
503.288304
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)
UREWIIMMOQCUKE-IGSJZTSJSA-N
InChi (Click to copy)
InChI=1S/C28H41NO7/c1-19(13-9-7-5-3-4-6-8-10-16-26(31)32)34-28-24(30)17-25(20(2)35-28)36-27(33)22-18-29-23-15-12-11-14-21(22)23/h11-12,14-15,18-20,24-25,28-30H,3-10,13,16-17H2,1-2H3,(H,31,32)/t19-,20+,24-,25-,28-/m1/s1
SMILES (Click to copy)
O([C@H](C)CCCCCCCCCCC(=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
79108
PubChem CID
86289756
SMID ID
icas#22

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 3
Aromatic Rings 2
Rotatable Bonds 16
Van der Waals Molecular Volume 490.77
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 6.86
Molar Refractivity 139.31

Admin

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