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CHEBI:79062 - icas#15

ChEBI IDCHEBI:79062
ChEBI Nameicas#15
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E,9R)-9-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](CCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C25H33NO7/c1-16(10-6-4-3-5-7-13-23(28)29)31-25-21(27)14-22(17(2)32-25)33-24(30)19-15-26-20-12-9-8-11-18(19)20/h7-9,11-13,15-17,21-22,25-27H,3-6,10,14H2,1-2H3,(H,28,29)/b13-7+/t16-,17+,21-,22-,25-/m1/s1
InChIKeyUSUOYFVGXSARBX-PHFSXSHVSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs28(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)
icas#15 (CHEBI:79062) has functional parent (2E,9R)-9-hydroxydec-2-enoic acid (CHEBI:78853)
icas#15 (CHEBI:79062) has functional parent ascr#15 (CHEBI:78852)
icas#15 (CHEBI:79062) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#15 (CHEBI:79062) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#15 (CHEBI:79062) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#15 (CHEBI:79062) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,9RR)-9-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}dec-2-enoic acid
Synonym  Source
9R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic acidSMID
Manual XrefsDatabases
icas%2315%0DSMID
Registry NumbersSources
Reaxys:22233464Reaxys
CAS:1355682-99-3SMID
Citations