Structure Database (LMSD)

Common Name
icas#9
Systematic Name
4R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino- hexopyranosyloxy)-pentanoic acid
Synonyms
  • 4R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acid
  • indolecarboxylascaroside C5
LM ID
LMFA13040128
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)
An indole-containing dauer pheromone component with unusual dauer inhibitory activity at higher concentrations.,
Org Lett, 2009
Pubmed ID: 19545143

String Representations

InChiKey (Click to copy)
GIZBXORWWXIWKX-VEZRURDRSA-N
InChi (Click to copy)
InChI=1S/C20H25NO7/c1-11(7-8-18(23)24)26-20-16(22)9-17(12(2)27-20)28-19(25)14-10-21-15-6-4-3-5-13(14)15/h3-6,10-12,16-17,20-22H,7-9H2,1-2H3,(H,23,24)/t11-,12+,16-,17-,20-/m1/s1
SMILES (Click to copy)
O([C@H](C)CCC(=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
79028
PubChem CID
44205814
SMID ID
icas#9

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 2
Rotatable Bonds 8
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
14th Jun 2020
Updated at
28th Oct 2021