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CHEBI:131396 - (2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide

ChEBI IDCHEBI:131396
ChEBI Name(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide
Stars
ASCII Name(2E,24R)-24-[(alpha-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide
DefinitionA hydroxy fatty amide ascaroside obtained by obtained by formal condensation of the 24-hydroxy group of (2E,24R)-24-hydroxy-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified7 March 2018
SubmitterSteve
DownloadsMolfile
FormulaC34H65NO6
Net Charge0
Average Mass583.895
Monoisotopic Mass583.48119
SMILESC/C(=C\CCCCCCCCCCCCCCCCCCCC[C@@H](C)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O)C(=O)NCCO
InChIInChI=1S/C34H65NO6/c1-28(33(39)35-25-26-36)23-21-19-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-20-22-24-29(2)40-34-32(38)27-31(37)30(3)41-34/h23,29-32,34,36-38H,4-22,24-27H2,1-3H3,(H,35,39)/b28-23+/t29-,30+,31-,32-,34-/m1/s1
InChIKeyXONAGBHTCVDMMT-HGZOCMNVSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (23163760)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide (CHEBI:131396) has role Caenorhabditis elegans metabolite (CHEBI:78804)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide (CHEBI:131396) is a N-acylethanolamine (CHEBI:52640)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide (CHEBI:131396) is a enamide (CHEBI:51751)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide (CHEBI:131396) is a hydroxy fatty amide ascaroside (CHEBI:131400)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide (CHEBI:131396) is a secondary carboxamide (CHEBI:140325)
IUPAC Name 
(2E,24R)-24-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-N-(2-hydroxyethyl)-2-methylpentacos-2-enamide
Synonym  Source
(24R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-methyl-2E-pentacosenoic acid ethanolamideChEBI
Registry NumbersSources
Reaxys:23412669Reaxys
Citations