Structure database (LMSD)

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LM IDLMFA13040026
Common Nameascr#27
Systematic Name15R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-hexadecenoic acid
Synonyms15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
hexadecenoic acid
Exact Mass
400.2825 (neutral)    Calculate m/z:
FormulaC22H40O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289698
CHEBI ID78965
InChIKeyPHSQDXKUQRUWOG-PXMSNCRXSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C22H40O6/c1-17(27-22-20(24)16-19(23)18(2)28-22)14-12-10-8-6-4-3-5-7-9-11-13-15-21(25)26/h13,15,17-20,22-24H,3-12,14,16H2,1-2H3,(H,25,26)/b15-13+/t17-,18+,19-,20-,22-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCCC/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 Atoms28Rings1Aromatic Rings0Rotatable Bonds15
 van der Waals
Molecular Volume
424.26Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP5.61Molar
Refractivity
111.64