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CHEBI:79375 - ibho#24

ChEBI IDCHEBI:79375
ChEBI Nameibho#24
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#24 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
FormulaC29H43NO8
Net Charge0
Average Mass533.662
Monoisotopic Mass533.29887
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C29H43NO8/c1-20-26(38-28(35)23-19-30-24-15-11-10-14-22(23)24)18-25(32)29(37-20)36-16-12-8-6-4-2-3-5-7-9-13-21(31)17-27(33)34/h10-11,14-15,19-21,25-26,29-32H,2-9,12-13,16-18H2,1H3,(H,33,34)/t20-,21+,25+,26+,29+/m0/s1
InChIKeyLXVPUPUKAHIWDZ-STNUDKPESA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239)
- PubMed (22239548) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms
- 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#24 (CHEBI:79375) has functional parent (3R)-3,14-dihydroxymyristic acid (CHEBI:79281)
ibho#24 (CHEBI:79375) has functional parent bhos#24 (CHEBI:79262)
ibho#24 (CHEBI:79375) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#24 (CHEBI:79375) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#24 (CHEBI:79375) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#24 (CHEBI:79375) is a monocarboxylic acid (CHEBI:25384)
ibho#24 (CHEBI:79375) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-14-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytetradecanoic acid
Synonyms  Source
(3R)-14-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxymyristic acidChEBI
3R-hydroxy-14-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-myristic acidChEBI
3R-hydroxy-14-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acidSMID
Manual XrefsDatabases
ibho%2324SMID
Registry NumbersSources
Reaxys:23412686Reaxys
CAS:1355683-47-4SMID
Citations