Structure database (LMSD)

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LM IDLMFA13040017
Common Nameascr#37
Systematic Name20R-(3,6-dideoxy-α-L-arabino-hexopyranosyloxy)-2E-heneicosenoic acid
Synonyms20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-
henicosenoic acid
Exact Mass
470.3607 (neutral)    Calculate m/z:
FormulaC27H50O6
CategoryFatty Acyls [FA]
Main ClassFatty acyl glycosides [FA13]
Sub ClassAscarosides [FA1304]
PubChem CID86289708
CHEBI ID78975
InChIKeyIRXQRQDBIJEMEI-OQERHXAMSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C27H50O6/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/h18,20,22-25,27-29H,3-17,19,21H2,1-2H3,(H,30,31)/b20-18+/t22-,23+,24-,25-,27-/m1/s1
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SMILES
O([C@@H](CCCCCCCCCCCCCCCC/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 Atoms33Rings1Aromatic Rings0Rotatable Bonds20
 van der Waals
Molecular Volume
510.76Topological Polar
Surface Area
98.29Hydrogen
Bond Donors
3Hydrogen
Bond Acceptors
6
 logP7.56Molar
Refractivity
134.72