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CHEBI:79356 - ibha#22

ChEBI IDCHEBI:79356
ChEBI Nameibha#22
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#22 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
FormulaC28H41NO8
Net Charge0
Average Mass519.635
Monoisotopic Mass519.28322
SMILESC[C@H](CCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C28H41NO8/c1-18(11-7-5-3-4-6-8-12-20(30)15-26(32)33)35-28-24(31)16-25(19(2)36-28)37-27(34)22-17-29-23-14-10-9-13-21(22)23/h9-10,13-14,17-20,24-25,28-31H,3-8,11-12,15-16H2,1-2H3,(H,32,33)/t18-,19+,20-,24-,25-,28-/m1/s1
InChIKeySUECAIROUVPYHD-JZBHREIRSA-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#22 (CHEBI:79356) has functional parent (3R,12R)-3,12-dihydroxytridecanoic acid (CHEBI:79244)
ibha#22 (CHEBI:79356) has functional parent bhas#22 (CHEBI:79231)
ibha#22 (CHEBI:79356) has functional parent icas#22 (CHEBI:79108)
ibha#22 (CHEBI:79356) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#22 (CHEBI:79356) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#22 (CHEBI:79356) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#22 (CHEBI:79356) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#22 (CHEBI:79356) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,12R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytridecanoic acid
Synonym  Source
3R-hydroxy-12R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acidSMID
Manual XrefsDatabases
ibha%2322SMID
Registry NumbersSources
Reaxys:22233523Reaxys
CAS:1355683-28-1SMID
Citations