LIPID MAPS

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

Status

Active

Exact Mass

Calculate m/z

389.183839

Formula

C₂₁H₂₇NO₆

Show lipids differing only in stereochemistry/bond geometry

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MDLMOL SDF CSV TSV

MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".

Classification

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

Reference

Selective MS Screening Reveals a Sex Pheromone in Caenorhabditis Briggsae and Species-Specificity in Indole Ascaroside Signalling
Org Biomol Chem. 2016
DOI: 10.1039/c6ob01230b
PMID: 27381649

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