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CHEBI:79371 - ibho#16

ChEBI IDCHEBI:79371
ChEBI Nameibho#16
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#16 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
FormulaC25H35NO8
Net Charge0
Average Mass477.554
Monoisotopic Mass477.23627
SMILESC[C@@H]1O[C@@H](OCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C25H35NO8/c1-16-22(34-24(31)19-15-26-20-11-7-6-10-18(19)20)14-21(28)25(33-16)32-12-8-4-2-3-5-9-17(27)13-23(29)30/h6-7,10-11,15-17,21-22,25-28H,2-5,8-9,12-14H2,1H3,(H,29,30)/t16-,17+,21+,22+,25+/m0/s1
InChIKeyIHRBCDQOWOHXDO-CGHZYJDXSA-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#16 (CHEBI:79371) has functional parent (3R)-3,10-dihydroxydecanoic acid (CHEBI:79272)
ibho#16 (CHEBI:79371) has functional parent bhos#16 (CHEBI:79258)
ibho#16 (CHEBI:79371) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#16 (CHEBI:79371) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#16 (CHEBI:79371) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#16 (CHEBI:79371) is a monocarboxylic acid (CHEBI:25384)
ibho#16 (CHEBI:79371) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydecanoic acid
Synonym  Source
3R-hydroxy-10-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acidSMID
Manual XrefsDatabases
ibho%2316SMID
Registry NumbersSources
Reaxys:22233491Reaxys
CAS:1355683-39-4SMID
Citations