Structure Database (LMSD)

Common Name
hbas#3
Systematic Name
8R-(3,6-dideoxy-(4-O-hydroxybenzoyl)α-L-arabino-hexopyranosyloxy)-2E-nonenoic acid
Synonyms
  • 8R-(3'R-hydroxy-5'R-O-(4-hydroxybenzoyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acid
LM ID
LMFA13040147
Formula
C22H30O8
Exact Mass
Calculate m/z
422.19407
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)
BJUWUCQZCXGYNI-NJABCCJWSA-N
InChi (Click to copy)
InChI=1S/C22H30O8/c1-14(7-5-3-4-6-8-20(25)26)28-22-18(24)13-19(15(2)29-22)30-21(27)16-9-11-17(23)12-10-16/h6,8-12,14-15,18-19,22-24H,3-5,7,13H2,1-2H3,(H,25,26)/b8-6+/t14-,15+,18-,19-,22-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](OC(=O)C2=CC=C(O)C=C2)[C@H](C)O1

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

Other Databases

CHEBI ID
79321
PubChem CID
86289885
SMID ID
hbas#3

Calculated Physicochemical Properties

Heavy Atoms 30
Rings 2
Aromatic Rings 1
Rotatable Bonds 11
Van der Waals Molecular Volume 408.02
Topological Polar Surface Area 124.59
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 8
logP 4.45
Molar Refractivity 110.62

Admin

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