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CHEBI:79117 - icos#10

ChEBI IDCHEBI:79117
ChEBI Nameicos#10
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from 9-hydroxynonanoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC24H33NO7
Net Charge0
Average Mass447.528
Monoisotopic Mass447.22570
SMILESC[C@@H]1O[C@@H](OCCCCCCCCC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C24H33NO7/c1-16-21(32-23(29)18-15-25-19-11-8-7-10-17(18)19)14-20(26)24(31-16)30-13-9-5-3-2-4-6-12-22(27)28/h7-8,10-11,15-16,20-21,24-26H,2-6,9,12-14H2,1H3,(H,27,28)/t16-,20+,21+,24+/m0/s1
InChIKeyLAOIIVMDNNIKFB-IAPYZZODSA-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#10 (CHEBI:79117) has functional parent 9-hydroxynonanoic acid (CHEBI:79121)
icos#10 (CHEBI:79117) has functional parent oscr#10 (CHEBI:79134)
icos#10 (CHEBI:79117) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icos#10 (CHEBI:79117) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icos#10 (CHEBI:79117) is a monocarboxylic acid (CHEBI:25384)
icos#10 (CHEBI:79117) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
9-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}nonanoic acid
Synonym  Source
9-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acidSMID
Manual XrefsDatabases
icos%2310%0DSMID
Registry NumbersSources
Reaxys:22233461Reaxys
CAS:1355681-35-4SMID
Citations