Structure Database (LMSD)

Common Name
icas#2
Systematic Name
5R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino- hexopyranosyloxy)-hexan-2-one
Synonyms
  • (2S,3R,5R,6R)-5-hydroxy-2-methyl-6-(((R)-5-oxohexan-2-yl)oxy)tetrahydro-2H-pyran-3-yl 1H-indole-3-carboxylate
LM ID
LMFA13040129
Formula
C21H27NO6
Exact Mass
Calculate m/z
389.183839
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)
Selective MS screening reveals a sex pheromone in Caenorhabditis briggsae and species-specificity in indole ascaroside signalling.,
Org Biomol Chem, 2016
Pubmed ID: 27381649

String Representations

InChiKey (Click to copy)
VNOOSCCMEMBAAB-BEMBYLKPSA-N
InChi (Click to copy)
InChI=1S/C21H27NO6/c1-12(23)8-9-13(2)26-21-18(24)10-19(14(3)27-21)28-20(25)16-11-22-17-7-5-4-6-15(16)17/h4-7,11,13-14,18-19,21-22,24H,8-10H2,1-3H3/t13-,14+,18-,19-,21-/m1/s1
SMILES (Click to copy)
O([C@H](C)CCC(=O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

Other Databases

PubChem CID
132934130
SMID ID
icas#2

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 2
Rotatable Bonds 8
Van der Waals Molecular Volume 360.88
Topological Polar Surface Area 99.92
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 7
logP 4.24
Molar Refractivity 105.42

Admin

Created at
14th Jun 2020
Updated at
28th Oct 2021