Structure database (LMSD)

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LM IDLMFA13040021
Common Nameascr#33
Systematic Name18R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-nonadecenoic acid
Synonyms18R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
nonadecenoic acid
Exact Mass
442.3294 (neutral)    Calculate m/z:
FormulaC25H46O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289704
CHEBI ID78971
InChIKeyJQBYGLLYFPDQJA-NVJHKYEUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C25H46O6/c1-20(30-25-23(27)19-22(26)21(2)31-25)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-24(28)29/h16,18,20-23,25-27H,3-15,17,19H2,1-2H3,(H,28,29)/b18-16+/t20-,21+,22-,23-,25-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCCCCCC/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 Atoms31Rings1Aromatic Rings0Rotatable Bonds18
 van der Waals
Molecular Volume
476.16Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP6.78Molar
Refractivity
125.49