EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:79106 - icas#19

ChEBI IDCHEBI:79106
ChEBI Nameicas#19
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E,11R)-11-hydroxydodec-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H37NO7
Net Charge0
Average Mass487.593
Monoisotopic Mass487.25700
SMILESC[C@H](CCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C27H37NO7/c1-18(12-8-6-4-3-5-7-9-15-25(30)31)33-27-23(29)16-24(19(2)34-27)35-26(32)21-17-28-22-14-11-10-13-20(21)22/h9-11,13-15,17-19,23-24,27-29H,3-8,12,16H2,1-2H3,(H,30,31)/b15-9+/t18-,19+,23-,24-,27-/m1/s1
InChIKeyCQSBSCBIGYDANS-OQGVURBQSA-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#19 (CHEBI:79106) has functional parent (2E,11R)-11-hydroxydodec-2-enoic acid (CHEBI:78977)
icas#19 (CHEBI:79106) has functional parent ascr#19 (CHEBI:78957)
icas#19 (CHEBI:79106) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#19 (CHEBI:79106) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#19 (CHEBI:79106) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#19 (CHEBI:79106) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,11R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}dodec-2-enoic acid
Synonym  Source
11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-dodecenoic acidSMID
Manual XrefsDatabases
icas%2319%0DSMID
Registry NumbersSources
Reaxys:22233492Reaxys
CAS:1355683-08-7SMID
Citations