Structure Database (LMSD)

Common Name
ascr#21
Systematic Name
12R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-tridecanoic acid
Synonyms
  • 12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tridecanoic acid
LM ID
LMFA13040011
Formula
C19H34O6
Exact Mass
Calculate m/z
358.23554
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)
XUGAOOQYBZSMCP-ZXSNAGKJSA-N
InChi (Click to copy)
InChI=1S/C19H34O6/c1-14(24-19-17(21)13-16(20)15(2)25-19)11-9-7-5-3-4-6-8-10-12-18(22)23/h10,12,14-17,19-21H,3-9,11,13H2,1-2H3,(H,22,23)/b12-10+/t14-,15+,16-,17-,19-/m1/s1
SMILES (Click to copy)
O([C@@H](CCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1

Other Databases

CHEBI ID
78959
PubChem CID
86289692
SMID ID
ascr#21

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 372.36
Topological Polar Surface Area 98.29
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 6
logP 4.44
Molar Refractivity 97.78

Admin

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