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CHEBI:79052 - icas#3

ChEBI IDCHEBI:79052
ChEBI Nameicas#3
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (2E,8R)-8-hydroxynon-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC24H31NO7
Net Charge0
Average Mass445.512
Monoisotopic Mass445.21005
SMILESC[C@H](CCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C24H31NO7/c1-15(9-5-3-4-6-12-22(27)28)30-24-20(26)13-21(16(2)31-24)32-23(29)18-14-25-19-11-8-7-10-17(18)19/h6-8,10-12,14-16,20-21,24-26H,3-5,9,13H2,1-2H3,(H,27,28)/b12-6+/t15-,16+,20-,21-,24-/m1/s1
InChIKeyMHHAGCKXSLPDOU-SUOYGWGXSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(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#3 (CHEBI:79052) has functional parent (2E,8R)-8-hydroxynon-2-enoic acid (CHEBI:78819)
icas#3 (CHEBI:79052) has functional parent ascr#3 (CHEBI:78821)
icas#3 (CHEBI:79052) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#3 (CHEBI:79052) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#3 (CHEBI:79052) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#3 (CHEBI:79052) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,8R)-8-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}non-2-enoic acid
Synonym  Source
8R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acidSMID
Manual XrefsDatabases
icas%233%0DSMID
Registry NumbersSources
Reaxys:22233454Reaxys
CAS:1355681-39-8SMID
Citations