Structure database (LMSD)

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LM IDLMFA13040012
Common Nameascr#25
Systematic Name14R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-pentadecanoic acid
Synonyms14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
pentadecanoic acid
Exact Mass
386.2668 (neutral)    Calculate m/z:
FormulaC21H38O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289696
CHEBI ID78963
InChIKeyMTVUVHUAEUQKIN-YWWXTUTHSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C21H38O6/c1-16(26-21-19(23)15-18(22)17(2)27-21)13-11-9-7-5-3-4-6-8-10-12-14-20(24)25/h12,14,16-19,21-23H,3-11,13,15H2,1-2H3,(H,24,25)/b14-12+/t16-,17+,18-,19-,21-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCC/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 Atoms27Rings1Aromatic Rings0Rotatable Bonds14
 van der Waals
Molecular Volume
406.96Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP5.22Molar
Refractivity
107.02