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CHEBI:79118 - icos#15

ChEBI IDCHEBI:79118
ChEBI Nameicos#15
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E)-10-hydroxydec-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H33NO7
Net Charge0
Average Mass459.539
Monoisotopic Mass459.22570
SMILESC[C@@H]1O[C@@H](OCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C25H33NO7/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/h7-9,11-13,16-17,21-22,25-27H,2-6,10,14-15H2,1H3,(H,28,29)/b13-7+/t17-,21+,22+,25+/m0/s1
InChIKeySCZSSSOEHFCMKR-ONIXZVGUSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) 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#15 (CHEBI:79118) has functional parent (E)-10-hydroxydec-2-enoic acid (CHEBI:78668)
icos#15 (CHEBI:79118) has functional parent oscr#15 (CHEBI:79137)
icos#15 (CHEBI:79118) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icos#15 (CHEBI:79118) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icos#15 (CHEBI:79118) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
icos#15 (CHEBI:79118) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(2E)-10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}dec-2-enoic acid
Synonym  Source
10-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic acidSMID
Manual XrefsDatabases
icos%2315%0DSMID
Registry NumbersSources
Reaxys:22233472Reaxys
CAS:1355683-13-4SMID
Citations