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CHEBI:79376 - ibho#26

ChEBI IDCHEBI:79376
ChEBI Nameibho#26
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside that is bhos#26 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
FormulaC30H45NO8
Net Charge0
Average Mass547.689
Monoisotopic Mass547.31452
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCC[C@@H](O)CC(=O)O)[C@H](O)C[C@H]1OC(=O)c1cnc2ccccc12
InChIInChI=1S/C30H45NO8/c1-21-27(39-29(36)24-20-31-25-16-12-11-15-23(24)25)19-26(33)30(38-21)37-17-13-9-7-5-3-2-4-6-8-10-14-22(32)18-28(34)35/h11-12,15-16,20-22,26-27,30-33H,2-10,13-14,17-19H2,1H3,(H,34,35)/t21-,22+,26+,27+,30+/m0/s1
InChIKeyHVABDZVINXGTFF-PSEFKOPQSA-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#26 (CHEBI:79376) has functional parent (3R)-3,15-dihydroxypentadecanoic acid (CHEBI:79282)
ibho#26 (CHEBI:79376) has functional parent bhos#26 (CHEBI:79263)
ibho#26 (CHEBI:79376) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#26 (CHEBI:79376) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#26 (CHEBI:79376) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#26 (CHEBI:79376) is a monocarboxylic acid (CHEBI:25384)
ibho#26 (CHEBI:79376) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
IUPAC Name 
(3R)-15-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxypentadecanoic acid
Synonym  Source
3R-hydroxy-15-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acidSMID
Manual XrefsDatabases
ibho%2326SMID
Registry NumbersSources
Reaxys:22233529Reaxys
CAS:1355683-49-6SMID
Citations