Structure Database (LMSD)

Common Name
icas#10
Systematic Name
8R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-nonanoic acid
Synonyms
  • 8R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)- tetrahydropyran-2'-yloxy)-nonanoic acid
LM ID
LMFA13040125
Formula
C24H33NO7
Exact Mass
Calculate m/z
447.225704
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)
VGNCAEIQHDZOLI-JTCUFRKPSA-N
InChi (Click to copy)
InChI=1S/C24H33NO7/c1-15(9-5-3-4-6-12-22(27)28)30-24-20(26)13-21(16(2)31-24)32-23(29)18-14-25-19-11-8-7-10-17(18)19/h7-8,10-11,14-16,20-21,24-26H,3-6,9,12-13H2,1-2H3,(H,27,28)/t15-,16+,20-,21-,24-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCC(=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
79029
PubChem CID
86289731
SMID ID
icas#10

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 3
Aromatic Rings 2
Rotatable Bonds 12
Van der Waals Molecular Volume 421.57
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 5.29
Molar Refractivity 120.84

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