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CHEBI:79354 - ibha#18

ChEBI IDCHEBI:79354
ChEBI Nameibha#18
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#18 in which the pro-R hydrogen β to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H37NO8
Net Charge0
Average Mass491.581
Monoisotopic Mass491.25192
SMILESC[C@H](CCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C26H37NO8/c1-16(9-5-3-4-6-10-18(28)13-24(30)31)33-26-22(29)14-23(17(2)34-26)35-25(32)20-15-27-21-12-8-7-11-19(20)21/h7-8,11-12,15-18,22-23,26-29H,3-6,9-10,13-14H2,1-2H3,(H,30,31)/t16-,17+,18-,22-,23-,26-/m1/s1
InChIKeyQHLYWGFFZVVDPY-CRZRSRDBSA-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)
ibha#18 (CHEBI:79354) has functional parent (3R,10R)-3,10-dihydroxyundecanoic acid (CHEBI:79242)
ibha#18 (CHEBI:79354) has functional parent bhas#18 (CHEBI:79229)
ibha#18 (CHEBI:79354) has functional parent icas#18 (CHEBI:79105)
ibha#18 (CHEBI:79354) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#18 (CHEBI:79354) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#18 (CHEBI:79354) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#18 (CHEBI:79354) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#18 (CHEBI:79354) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,10R)-10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyundecanoic acid
Synonym  Source
3R-hydroxy-10R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
Manual XrefsDatabases
ibha%2318SMID
Registry NumbersSources
Reaxys:22233506Reaxys
CAS:1355683-24-7SMID
Citations