Structure Database (LMSD)

Common Name
ascr#29
Systematic Name
16R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-heptadecenoic acid
Synonyms
  • 16R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptadecenoic acid
LM ID
LMFA13040025
Formula
C23H42O6
Exact Mass
Calculate m/z
414.29814
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)
XUIDIXMFLJXJDI-XUAZKPKSSA-N
InChi (Click to copy)
InChI=1S/C23H42O6/c1-18(28-23-21(25)17-20(24)19(2)29-23)15-13-11-9-7-5-3-4-6-8-10-12-14-16-22(26)27/h14,16,18-21,23-25H,3-13,15,17H2,1-2H3,(H,26,27)/b16-14+/t18-,19+,20-,21-,23-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78967
PubChem CID
86289700
SMID ID
ascr#29

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 1
Aromatic Rings 0
Rotatable Bonds 16
Van der Waals Molecular Volume 441.56
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 6.00
Molar Refractivity 116.25

Admin

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