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CHEBI:79358 - ibha#26

ChEBI IDCHEBI:79358
ChEBI Nameibha#26
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is bhas#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](CCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C30H45NO8/c1-20(13-9-7-5-3-4-6-8-10-14-22(32)17-28(34)35)37-30-26(33)18-27(21(2)38-30)39-29(36)24-19-31-25-16-12-11-15-23(24)25/h11-12,15-16,19-22,26-27,30-33H,3-10,13-14,17-18H2,1-2H3,(H,34,35)/t20-,21+,22-,26-,27-,30-/m1/s1
InChIKeyUWTXRGDQDGZEBX-RZEARGRZSA-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)
ibha#26 (CHEBI:79358) has functional parent (3R,14R)-3,14-dihydroxypentadecanoic acid (CHEBI:79247)
ibha#26 (CHEBI:79358) has functional parent bhas#26 (CHEBI:79233)
ibha#26 (CHEBI:79358) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#26 (CHEBI:79358) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#26 (CHEBI:79358) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#26 (CHEBI:79358) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#26 (CHEBI:79358) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,14R)-14-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxypentadecanoic acid
Synonym  Source
3R-hydroxy-14R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acidSMID
Manual XrefsDatabases
ibha%2326%0DSMID
Registry NumbersSources
Reaxys:22233530Reaxys
CAS:1355683-32-7SMID
Citations