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CHEBI:131403 - (2E,24R)-24-[(α-L-ascarosyl)oxy]-2-methylpentacos-2-enoic acid

ChEBI IDCHEBI:131403
ChEBI Name(2E,24R)-24-[(α-L-ascarosyl)oxy]-2-methylpentacos-2-enoic acid
Stars
ASCII Name(2E,24R)-24-[(alpha-L-ascarosyl)oxy]-2-methylpentacos-2-enoic acid
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by obtained by formal condensation of the alcoholic hydroxy group of (2E,24R)-2-methylpentacos-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified2 March 2016
SubmitterSteve
DownloadsMolfile
FormulaC32H60O6
Net Charge0
Average Mass540.826
Monoisotopic Mass540.43899
SMILESC/C(=C\CCCCCCCCCCCCCCCCCCCC[C@@H](C)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O)C(=O)O
InChIInChI=1S/C32H60O6/c1-26(31(35)36)23-21-19-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-20-22-24-27(2)37-32-30(34)25-29(33)28(3)38-32/h23,27-30,32-34H,4-22,24-25H2,1-3H3,(H,35,36)/b26-23+/t27-,28+,29-,30-,32-/m1/s1
InChIKeyJZKOIAZAXRNJDG-DDVOXAPDSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (23163760)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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]-2-methylpentacos-2-enoic acid (CHEBI:131403) has role Caenorhabditis elegans metabolite (CHEBI:78804)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-2-methylpentacos-2-enoic acid (CHEBI:131403) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
(2E,24R)-24-[(α-L-ascarosyl)oxy]-2-methylpentacos-2-enoic acid (CHEBI:131403) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,24R)-24-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-2-methylpentacos-2-enoic acid
Synonym  Source
(24R)-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-methyl-2E-pentacosenoic acidChEBI
Registry NumbersSources
Reaxys:23412670Reaxys
Citations