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CHEBI:79023 - icas#7

ChEBI IDCHEBI:79023
ChEBI Nameicas#7
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E,6R)-6-hydroxyhept-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H27NO7
Net Charge0
Average Mass417.458
Monoisotopic Mass417.17875
SMILESC[C@H](CC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C22H27NO7/c1-13(7-3-6-10-20(25)26)28-22-18(24)11-19(14(2)29-22)30-21(27)16-12-23-17-9-5-4-8-15(16)17/h4-6,8-10,12-14,18-19,22-24H,3,7,11H2,1-2H3,(H,25,26)/b10-6+/t13-,14+,18-,19-,22-/m1/s1
InChIKeyOVHQEHRYORHTRQ-KXXILVSQSA-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)
icas#7 (CHEBI:79023) has functional parent (2E,6R)-6-hydroxyhept-2-enoic acid (CHEBI:78831)
icas#7 (CHEBI:79023) has functional parent ascr#7 (CHEBI:78830)
icas#7 (CHEBI:79023) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#7 (CHEBI:79023) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#7 (CHEBI:79023) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#7 (CHEBI:79023) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,6R)-6-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}hept-2-enoic acid
Synonym  Source
6R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptenoic acidSMID
Manual XrefsDatabases
icas%237%0DSMID
Registry NumbersSources
Reaxys:22233433Reaxys
CAS:1355682-94-8SMID
Citations