Structure Database (LMSD)

Common Name
ascr#38
Systematic Name
20R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-heneicosanoic acid
Synonyms
  • 20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-henicosenoic acid
LM ID
LMFA13040016
Formula
C27H52O6
Exact Mass
Calculate m/z
472.37639
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)
NISHIBVYPLRXFI-VYXBAIFMSA-N
InChi (Click to copy)
InChI=1S/C27H52O6/c1-22(32-27-25(29)21-24(28)23(2)33-27)19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-26(30)31/h22-25,27-29H,3-21H2,1-2H3,(H,30,31)/t22-,23+,24-,25-,27-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCCCCCCCCC(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78976
PubChem CID
86289709
SMID ID
ascr#38

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 1
Aromatic Rings 0
Rotatable Bonds 21
Van der Waals Molecular Volume 513.40
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 7.79
Molar Refractivity 134.81

Admin

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