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CHEBI:79357 - ibha#24

ChEBI IDCHEBI:79357
ChEBI Nameibha#24
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is bhas#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](CCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C29H43NO8/c1-19(12-8-6-4-3-5-7-9-13-21(31)16-27(33)34)36-29-25(32)17-26(20(2)37-29)38-28(35)23-18-30-24-15-11-10-14-22(23)24/h10-11,14-15,18-21,25-26,29-32H,3-9,12-13,16-17H2,1-2H3,(H,33,34)/t19-,20+,21-,25-,26-,29-/m1/s1
InChIKeyVEGIRKJOIIBEHY-HFAWLSGZSA-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#24 (CHEBI:79357) has functional parent (3R,13R)-3,13-dihydroxymyristic acid (CHEBI:79245)
ibha#24 (CHEBI:79357) has functional parent bhas#24 (CHEBI:79232)
ibha#24 (CHEBI:79357) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#24 (CHEBI:79357) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#24 (CHEBI:79357) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#24 (CHEBI:79357) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#24 (CHEBI:79357) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,13R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytetradecanoic acid
Synonyms  Source
3R-hydroxy-13R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acidSMID
(3R,13R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxymyristic acidChEBI
3R-hydroxy-13R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-myristic acidChEBI
Manual XrefsDatabases
ibha%2324SMID
Registry NumbersSources
Reaxys:22233524Reaxys
CAS:1355683-30-5SMID
Citations