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CHEBI:79374 - ibho#22

ChEBI IDCHEBI:79374
ChEBI Nameibho#22
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#22 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
FormulaC28H41NO8
Net Charge0
Average Mass519.635
Monoisotopic Mass519.28322
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C28H41NO8/c1-19-25(37-27(34)22-18-29-23-14-10-9-13-21(22)23)17-24(31)28(36-19)35-15-11-7-5-3-2-4-6-8-12-20(30)16-26(32)33/h9-10,13-14,18-20,24-25,28-31H,2-8,11-12,15-17H2,1H3,(H,32,33)/t19-,20+,24+,25+,28+/m0/s1
InChIKeyFUIIPNLIVZGYJM-RHENGWIESA-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#22 (CHEBI:79374) has functional parent (3R)-3,13-dihydroxytridecanoic acid (CHEBI:79279)
ibho#22 (CHEBI:79374) has functional parent bhos#22 (CHEBI:79261)
ibho#22 (CHEBI:79374) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#22 (CHEBI:79374) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#22 (CHEBI:79374) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#22 (CHEBI:79374) is a monocarboxylic acid (CHEBI:25384)
ibho#22 (CHEBI:79374) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytridecanoic acid
Synonym  Source
3R-hydroxy-13-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acidSMID
Manual XrefsDatabases
ibho%2322SMID
Registry NumbersSources
Reaxys:22233520Reaxys
CAS:1355683-45-2SMID
Citations