Structure Database (LMSD)

Common Name
icas#12
Systematic Name
5R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-hexanoic acid
Synonyms
  • 5R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexanoic acid
LM ID
LMFA13040124
Formula
C21H27NO7
Exact Mass
Calculate m/z
405.178754
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)
AHNZPQNYGMNACV-PNNYZDKCSA-N
InChi (Click to copy)
InChI=1S/C21H27NO7/c1-12(6-5-9-19(24)25)27-21-17(23)10-18(13(2)28-21)29-20(26)15-11-22-16-8-4-3-7-14(15)16/h3-4,7-8,11-13,17-18,21-23H,5-6,9-10H2,1-2H3,(H,24,25)/t12-,13+,17-,18-,21-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCC(=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
79060
PubChem CID
86289742
SMID ID
icas#12

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 3
Aromatic Rings 2
Rotatable Bonds 9
Van der Waals Molecular Volume 369.67
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.12
Molar Refractivity 106.99

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