Structure Database (LMSD)

Common Name
icas#7
Systematic Name
6R-((1H-indol-3-ylcarbonyl)3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-heptenoic acid
Synonyms
  • 6R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptenoic acid
LM ID
LMFA13040127
Formula
C22H27NO7
Exact Mass
Calculate m/z
417.178754
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)
OVHQEHRYORHTRQ-KXXILVSQSA-N
InChi (Click to copy)
InChI=1S/C22H27NO7/c1-13(7-3-6-10-20(25)26)28-22-18(24)11-19(14(2)29-22)30-21(27)16-12-23-17-9-5-4-8-15(16)17/h4-6,8-10,12-14,18-19,22-24H,3,7,11H2,1-2H3,(H,25,26)/b10-6+/t13-,14+,18-,19-,22-/m1/s1
SMILES (Click to copy)
O([C@H](C)CC/C=C/C(=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
79023
PubChem CID
86289730
SMID ID
icas#7

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 3
Aromatic Rings 2
Rotatable Bonds 9
Van der Waals Molecular Volume 384.33
Topological Polar Surface Area 120.15
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.29
Molar Refractivity 111.51

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Created at
14th Jun 2020
Updated at
20th Oct 2021