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CHEBI:79353 - ibha#16

ChEBI IDCHEBI:79353
ChEBI Nameibha#16
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#16 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
FormulaC25H35NO8
Net Charge0
Average Mass477.554
Monoisotopic Mass477.23627
SMILESC[C@H](CCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C25H35NO8/c1-15(8-4-3-5-9-17(27)12-23(29)30)32-25-21(28)13-22(16(2)33-25)34-24(31)19-14-26-20-11-7-6-10-18(19)20/h6-7,10-11,14-17,21-22,25-28H,3-5,8-9,12-13H2,1-2H3,(H,29,30)/t15-,16+,17-,21-,22-,25-/m1/s1
InChIKeyKNTSMTUFIKIJQO-JUYTZFGZSA-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#16 (CHEBI:79353) has functional parent (3R,9R)-3,9-dihydroxydecanoic acid (CHEBI:79228)
ibha#16 (CHEBI:79353) has functional parent bhas#16 (CHEBI:79227)
ibha#16 (CHEBI:79353) has functional parent icas#16 (CHEBI:79094)
ibha#16 (CHEBI:79353) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#16 (CHEBI:79353) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#16 (CHEBI:79353) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#16 (CHEBI:79353) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#16 (CHEBI:79353) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,9R)-9-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydecanoic acid
Synonym  Source
3R-hydroxy-9R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acidSMID
Manual XrefsDatabases
ibha%2316%0DSMID
Registry NumbersSources
Reaxys:22233496Reaxys
CAS:1355683-39-4SMID
Citations