Structure database (LMSD)

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LM IDLMFA13040034
Common Nameascr#15
Systematic Name9R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-decenoic acid
Synonyms9R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic
acid
Exact Mass
316.1886 (neutral)    Calculate m/z:
FormulaC16H28O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289666
CHEBI ID78852
InChIKeyMZJGOAYSXTVLMG-NSKGPKHTSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
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
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SMILES
O([C@@H](CCCCC/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 Atoms22Rings1Aromatic Rings0Rotatable Bonds9
 van der Waals
Molecular Volume
320.46Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP3.27Molar
Refractivity
83.93