Structure Database (LMSD)

Common Name
icas#6.2
Systematic Name
5R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-hexan-2S-ol
Synonyms
  • (2S,3R,5R,6R)-5-hydroxy-6-(((2S,5R)-5-hydroxyhexan-2-yl)oxy)-2-methyltetrahydro-2H-pyran-3-yl-1H-indole-3-carboxylate
LM ID
LMFA13040131
Formula
C21H29NO6
Exact Mass
Calculate m/z
391.199489
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty acyl glycosides [FA13]
Ascarosides [FA1304]

String Representations

InChiKey (Click to copy)
QMIWMBOAIXYIKO-GNGVNREASA-N
InChi (Click to copy)
InChI=1S/C21H29NO6/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/h4-7,11-14,18-19,21-24H,8-10H2,1-3H3/t12-,13+,14-,18+,19+,21+/m0/s1
SMILES (Click to copy)
O([C@H](C)CC[C@@H](O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CNC3C=CC=CC=32)[C@H](C)O1

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

Other Databases

PubChem CID
132934131
SMID ID
icas#6.2

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 3
Aromatic Rings 2
Rotatable Bonds 8
Van der Waals Molecular Volume 363.52
Topological Polar Surface Area 103.08
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 4.32
Molar Refractivity 106.93

Admin

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