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CHEBI:79104 - icas#17

ChEBI IDCHEBI:79104
ChEBI Nameicas#17
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E,10R)-10-hydroxyundec-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H35NO7
Net Charge0
Average Mass473.566
Monoisotopic Mass473.24135
SMILESC[C@H](CCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C26H35NO7/c1-17(11-7-5-3-4-6-8-14-24(29)30)32-26-22(28)15-23(18(2)33-26)34-25(31)20-16-27-21-13-10-9-12-19(20)21/h8-10,12-14,16-18,22-23,26-28H,3-7,11,15H2,1-2H3,(H,29,30)/b14-8+/t17-,18+,22-,23-,26-/m1/s1
InChIKeyKOWFSBKIGJUBRC-LBOPOTOASA-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#17 (CHEBI:79104) has functional parent (2E,10R)-10-hydroxyundec-2-enoic acid (CHEBI:78953)
icas#17 (CHEBI:79104) has functional parent ascr#17 (CHEBI:78952)
icas#17 (CHEBI:79104) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#17 (CHEBI:79104) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#17 (CHEBI:79104) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#17 (CHEBI:79104) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,10R)-10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}undec-2-enoic acid
Synonym  Source
10R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-undecenoic acidSMID
Manual XrefsDatabases
icas%2317%0DSMID
Registry NumbersSources
Reaxys:22233482Reaxys
CAS:1355683-03-2SMID
Citations