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CHEBI:79111 - icos#1

ChEBI IDCHEBI:79111
ChEBI Nameicos#1
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from 7-hydroxyheptanoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H29NO7
Net Charge0
Average Mass419.474
Monoisotopic Mass419.19440
SMILESC[C@@H]1O[C@@H](OCCCCCCC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C22H29NO7/c1-14-19(30-21(27)16-13-23-17-9-6-5-8-15(16)17)12-18(24)22(29-14)28-11-7-3-2-4-10-20(25)26/h5-6,8-9,13-14,18-19,22-24H,2-4,7,10-12H2,1H3,(H,25,26)/t14-,18+,19+,22+/m0/s1
InChIKeyJPMANLDTTFCEPQ-XYHOUYMGSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) 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#1 (CHEBI:79111) has functional parent 7-hydroxyheptanoic acid (CHEBI:79112)
icos#1 (CHEBI:79111) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icos#1 (CHEBI:79111) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icos#1 (CHEBI:79111) is a monocarboxylic acid (CHEBI:25384)
icos#1 (CHEBI:79111) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
7-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}heptanoic acid
Synonym  Source
7-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptanoic acidSMID
Manual XrefsDatabases
icos%231%0DSMID
Registry NumbersSources
Reaxys:22233440Reaxys
CAS:1355681-32-1SMID
Citations