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CHEBI:79334 - ibha#10

ChEBI IDCHEBI:79334
ChEBI Nameibha#10
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#10 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
FormulaC24H33NO8
Net Charge0
Average Mass463.527
Monoisotopic Mass463.22062
SMILESC[C@H](CCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C24H33NO8/c1-14(7-3-4-8-16(26)11-22(28)29)31-24-20(27)12-21(15(2)32-24)33-23(30)18-13-25-19-10-6-5-9-17(18)19/h5-6,9-10,13-16,20-21,24-27H,3-4,7-8,11-12H2,1-2H3,(H,28,29)/t14-,15+,16-,20-,21-,24-/m1/s1
InChIKeyRHSYRFCZUCKPGK-IQWQIVRHSA-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#10 (CHEBI:79334) has functional parent (3R,8R)-3,8-dihydroxynonanoic acid (CHEBI:79224)
ibha#10 (CHEBI:79334) has functional parent bhas#10 (CHEBI:79223)
ibha#10 (CHEBI:79334) has functional parent icas#10 (CHEBI:79029)
ibha#10 (CHEBI:79334) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#10 (CHEBI:79334) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#10 (CHEBI:79334) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#10 (CHEBI:79334) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#10 (CHEBI:79334) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,8R)-8-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxynonanoic acid
Synonym  Source
3R-hydroxy-8R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acidSMID
Manual XrefsDatabases
ibha%2310SMID
Registry NumbersSources
Reaxys:22233473Reaxys
CAS:1355683-20-3SMID
Citations