Structure Database (LMSD)

Common Name
ascr#15
Systematic Name
9R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-decenoic acid
Synonyms
  • 9R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic acid
LM ID
LMFA13040034
Formula
C16H28O6
Exact Mass
Calculate m/z
316.18859
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)
MZJGOAYSXTVLMG-NSKGPKHTSA-N
InChi (Click to copy)
InChI=1S/C16H28O6/c1-11(8-6-4-3-5-7-9-15(19)20)21-16-14(18)10-13(17)12(2)22-16/h7,9,11-14,16-18H,3-6,8,10H2,1-2H3,(H,19,20)/b9-7+/t11-,12+,13-,14-,16-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78852
PubChem CID
86289666
SMID ID
ascr#15

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 1
Aromatic Rings 0
Rotatable Bonds 9
Van der Waals Molecular Volume 320.46
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 3.27
Molar Refractivity 83.93

Admin

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