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CHEBI:79372 - ibho#18

ChEBI IDCHEBI:79372
ChEBI Nameibho#18
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#18 in which the hydroxy group at position 4 of the ascarylopyranose moiety has been has been converted to the corresponding 1H-indole-3-carboxylate ester. 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]1O[C@@H](OCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C26H37NO8/c1-17-23(35-25(32)20-16-27-21-12-8-7-11-19(20)21)15-22(29)26(34-17)33-13-9-5-3-2-4-6-10-18(28)14-24(30)31/h7-8,11-12,16-18,22-23,26-29H,2-6,9-10,13-15H2,1H3,(H,30,31)/t17-,18+,22+,23+,26+/m0/s1
InChIKeyKNUQGRSJUADXIR-SIHSWOPCSA-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)
ibho#18 (CHEBI:79372) has functional parent (3R)-3,11-dihydroxyundecanoic acid (CHEBI:79275)
ibho#18 (CHEBI:79372) has functional parent bhos#18 (CHEBI:79259)
ibho#18 (CHEBI:79372) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#18 (CHEBI:79372) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#18 (CHEBI:79372) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#18 (CHEBI:79372) is a monocarboxylic acid (CHEBI:25384)
ibho#18 (CHEBI:79372) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyundecanoic acid
Synonym  Source
3R-hydroxy-11-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
Manual XrefsDatabases
ibho%2318SMID
Registry NumbersSources
Reaxys:22233513Reaxys
CAS:1355683-41-8SMID
Citations