Structure Database (LMSD)

Common Name
ascr#33
Systematic Name
18R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-nonadecenoic acid
Synonyms
  • 18R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonadecenoic acid
LM ID
LMFA13040021
Formula
C25H46O6
Exact Mass
Calculate m/z
442.32944
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)
JQBYGLLYFPDQJA-NVJHKYEUSA-N
InChi (Click to copy)
InChI=1S/C25H46O6/c1-20(30-25-23(27)19-22(26)21(2)31-25)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-24(28)29/h16,18,20-23,25-27H,3-15,17,19H2,1-2H3,(H,28,29)/b18-16+/t20-,21+,22-,23-,25-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78971
PubChem CID
86289704
SMID ID
ascr#33

Calculated Physicochemical Properties

Heavy Atoms 31
Rings 1
Aromatic Rings 0
Rotatable Bonds 18
Van der Waals Molecular Volume 476.16
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 6.78
Molar Refractivity 125.49

Admin

Created at
12th Jun 2020
Updated at
12th Jun 2020