Structure database (LMSD)

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LM IDLMFA13040025
Common Nameascr#29
Systematic Name16R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-heptadecenoic acid
Synonyms16R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
heptadecenoic acid
Exact Mass
414.2981 (neutral)    Calculate m/z:
FormulaC23H42O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289700
CHEBI ID78967
InChIKeyXUIDIXMFLJXJDI-XUAZKPKSSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
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
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SMILES
O([C@@H](CCCCCCCCCCCC/C=C/C(=O)O)C)[C@H]1[C@H](O)C[C@@H](O)[C@H](C)O1
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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 Atoms29Rings1Aromatic Rings0Rotatable Bonds16
 van der Waals
Molecular Volume
441.56Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP6.00Molar
Refractivity
116.25