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CHEBI:79124 - icos#18

ChEBI IDCHEBI:79124
ChEBI Nameicos#18
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from 11-hydroxyundecanoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H37NO7
Net Charge0
Average Mass475.582
Monoisotopic Mass475.25700
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C26H37NO7/c1-18-23(34-25(31)20-17-27-21-13-10-9-12-19(20)21)16-22(28)26(33-18)32-15-11-7-5-3-2-4-6-8-14-24(29)30/h9-10,12-13,17-18,22-23,26-28H,2-8,11,14-16H2,1H3,(H,29,30)/t18-,22+,23+,26+/m0/s1
InChIKeyXUHBKQAFWINXBW-BXAZGIKQSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8), acox-1(ok2257), and maoc-1(hj13) mutant worms.
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)
icos#18 (CHEBI:79124) has functional parent 11-hydroxyundecanoic acid (CHEBI:79126)
icos#18 (CHEBI:79124) has functional parent oscr#18 (CHEBI:79140)
icos#18 (CHEBI:79124) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icos#18 (CHEBI:79124) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icos#18 (CHEBI:79124) is a monocarboxylic acid (CHEBI:25384)
icos#18 (CHEBI:79124) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}undecanoic acid
Synonym  Source
11-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
Manual XrefsDatabases
icos%2318SMID
Registry NumbersSources
Reaxys:22233493Reaxys
CAS:1355683-18-9SMID
Citations