Structure Database (LMSD)

Common Name
ascr#35
Systematic Name
19R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-eicosenoic acid
Synonyms
  • 19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-icosenoic acid
LM ID
LMFA13040018
Formula
C26H48O6
Exact Mass
Calculate m/z
456.34509
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)
GIUKRFWFBBFDTQ-LAOJQUNESA-N
InChi (Click to copy)
InChI=1S/C26H48O6/c1-21(31-26-24(28)20-23(27)22(2)32-26)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-25(29)30/h17,19,21-24,26-28H,3-16,18,20H2,1-2H3,(H,29,30)/b19-17+/t21-,22+,23-,24-,26-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78973
PubChem CID
86289706
SMID ID
ascr#35

Calculated Physicochemical Properties

Heavy Atoms 32
Rings 1
Aromatic Rings 0
Rotatable Bonds 19
Van der Waals Molecular Volume 493.46
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 7.17
Molar Refractivity 130.10

Admin

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