Structure Database (LMSD)

Common Name
icas#16
Systematic Name
9R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-decanoic acid
Synonyms
  • 9R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)- tetrahydropyran-2'-yloxy)-decanoic acid
LM ID
LMFA13040122
Formula
C25H35NO7
Exact Mass
Calculate m/z
461.241354
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)
IKCBQQSZKXPNLW-BPCUIQQOSA-N
InChi (Click to copy)
InChI=1S/C25H35NO7/c1-16(10-6-4-3-5-7-13-23(28)29)31-25-21(27)14-22(17(2)32-25)33-24(30)19-15-26-20-12-9-8-11-18(19)20/h8-9,11-12,15-17,21-22,25-27H,3-7,10,13-14H2,1-2H3,(H,28,29)/t16-,17+,21-,22-,25-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCC(=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
79094
PubChem CID
86289750
SMID ID
icas#16

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 3
Aromatic Rings 2
Rotatable Bonds 13
Van der Waals Molecular Volume 438.87
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 5.68
Molar Refractivity 125.45

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