Structure Database (LMSD)

Common Name
icos#9
Systematic Name
5-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-pentanoic acid
Synonyms
  • 5-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acid
LM ID
LMFA13040139
Formula
C20H25NO7
Exact Mass
Calculate m/z
391.163104
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)
PTAMECMDMIIEJC-XZVYQEECSA-N
InChi (Click to copy)
InChI=1S/C20H25NO7/c1-12-17(10-16(22)20(27-12)26-9-5-4-8-18(23)24)28-19(25)14-11-21-15-7-3-2-6-13(14)15/h2-3,6-7,11-12,16-17,20-22H,4-5,8-10H2,1H3,(H,23,24)/t12-,16+,17+,20+/m0/s1
SMILES (Click to copy)
O(CCCCC(=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
79116
PubChem CID
86289759
SMID ID
icos#9

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 2
Rotatable Bonds 9
Van der Waals Molecular Volume 352.37
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 3.73
Molar Refractivity 102.37

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