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CHEBI:79119 - icos#16

ChEBI IDCHEBI:79119
ChEBI Nameicos#16
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from 10-hydroxydecanoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H35NO7
Net Charge0
Average Mass461.555
Monoisotopic Mass461.24135
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C25H35NO7/c1-17-22(33-24(30)19-16-26-20-12-9-8-11-18(19)20)15-21(27)25(32-17)31-14-10-6-4-2-3-5-7-13-23(28)29/h8-9,11-12,16-17,21-22,25-27H,2-7,10,13-15H2,1H3,(H,28,29)/t17-,21+,22+,25+/m0/s1
InChIKeyFVKMIXWYNVQFGG-DZBFJFRRSA-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#16 (CHEBI:79119) has functional parent 10-hydroxycapric acid (CHEBI:17409)
icos#16 (CHEBI:79119) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icos#16 (CHEBI:79119) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icos#16 (CHEBI:79119) is a monocarboxylic acid (CHEBI:25384)
icos#16 (CHEBI:79119) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}decanoic acid
Synonym  Source
10-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acidSMID
Manual XrefsDatabases
icos%2316%0DSMID
Registry NumbersSources
Reaxys:22233471Reaxys
CAS:1355683-15-6SMID
Citations