Structure database (LMSD)

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LM IDLMFA13040029
Common Nameascr#24
Systematic Name13R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-tetradecanoic acid
Synonyms13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic
acid
Exact Mass
374.2668 (neutral)    Calculate m/z:
FormulaC20H38O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289695
CHEBI ID78962
InChIKeyNRXYKCLIMLPUIO-KWXDATOUSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C20H38O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h15-18,20-22H,3-14H2,1-2H3,(H,23,24)/t15-,16+,17-,18-,20-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCCCC(=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 Atoms26Rings1Aromatic Rings0Rotatable Bonds14
 van der Waals
Molecular Volume
392.30Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP5.06Molar
Refractivity
102.50