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CHEBI:79370 - ibho#10

ChEBI IDCHEBI:79370
ChEBI Nameibho#10
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#10 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
FormulaC24H33NO8
Net Charge0
Average Mass463.527
Monoisotopic Mass463.22062
SMILESC[C@@H]1O[C@@H](OCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C24H33NO8/c1-15-21(33-23(30)18-14-25-19-10-6-5-9-17(18)19)13-20(27)24(32-15)31-11-7-3-2-4-8-16(26)12-22(28)29/h5-6,9-10,14-16,20-21,24-27H,2-4,7-8,11-13H2,1H3,(H,28,29)/t15-,16+,20+,21+,24+/m0/s1
InChIKeyHYGXRAVBIUWTNN-HIYLOANVSA-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#10 (CHEBI:79370) has functional parent (3R)-3,9-dihydroxynonanoic acid (CHEBI:79257)
ibho#10 (CHEBI:79370) has functional parent bhos#10 (CHEBI:79256)
ibho#10 (CHEBI:79370) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#10 (CHEBI:79370) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#10 (CHEBI:79370) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#10 (CHEBI:79370) is a monocarboxylic acid (CHEBI:25384)
ibho#10 (CHEBI:79370) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-9-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxynonanoic acid
Synonym  Source
3R-hydroxy-9-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acidSMID
Manual XrefsDatabases
ibho%2310SMID
Registry NumbersSources
Reaxys:22233486Reaxys
CAS:1355683-38-3SMID
Citations