Structure database (LMSD)

  MDLMOL files can be opened in various drawing programs. In ChemDraw, open as filetype "MDL Molfile".
LM IDLMFA13040018
Common Nameascr#35
Systematic Name19R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-eicosenoic acid
Synonyms19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-icosenoic
acid
Exact Mass
456.3451 (neutral)    Calculate m/z:
FormulaC26H48O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289706
CHEBI ID78973
InChIKeyGIUKRFWFBBFDTQ-LAOJQUNESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
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
Click to highlight InChI
SMILES
O([C@@H](CCCCCCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1
Click to highlight SMILES
StatusActive
ReferencesComparative Metabolomics Reveals Biogenesis of Ascarosides, a Modular Library of Small-Molecule Signals in C. elegans
J Am Chem Soc. 2012
DOI: 10.1021/ja210202y
PMID: 22239548
Calculated physicochemical properties (?):
 Heavy Atoms32Rings1Aromatic Rings0Rotatable Bonds19
 van der Waals
Molecular Volume
493.46Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP7.17Molar
Refractivity
130.10