Structure database (LMSD)

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LM IDLMFA13040016
Common Nameascr#38
Systematic Name20R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-heneicosanoic acid
Synonyms20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-henicosenoic
acid
Exact Mass
472.3764 (neutral)    Calculate m/z:
FormulaC27H52O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289709
CHEBI ID78976
InChIKeyNISHIBVYPLRXFI-VYXBAIFMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H52O6/c1-22(32-27-25(29)21-24(28)23(2)33-27)19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-26(30)31/h22-25,27-29H,3-21H2,1-2H3,(H,30,31)/t22-,23+,24-,25-,27-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCCCCCCCCCCC(=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 Atoms33Rings1Aromatic Rings0Rotatable Bonds21
 van der Waals
Molecular Volume
513.40Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP7.79Molar
Refractivity
134.81