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CHEBI:79359 - ibha#28

ChEBI IDCHEBI:79359
ChEBI Nameibha#28
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is bhas#28 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
FormulaC31H47NO8
Net Charge0
Average Mass561.716
Monoisotopic Mass561.33017
SMILESC[C@H](CCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C31H47NO8/c1-21(14-10-8-6-4-3-5-7-9-11-15-23(33)18-29(35)36)38-31-27(34)19-28(22(2)39-31)40-30(37)25-20-32-26-17-13-12-16-24(25)26/h12-13,16-17,20-23,27-28,31-34H,3-11,14-15,18-19H2,1-2H3,(H,35,36)/t21-,22+,23-,27-,28-,31-/m1/s1
InChIKeyDVKTXYSVNVCEOI-FFDCXVHWSA-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#28 (CHEBI:79359) has functional parent (3R,15R)-3,15-dihydroxypalmitic acid (CHEBI:79248)
ibha#28 (CHEBI:79359) has functional parent bhas#28 (CHEBI:79234)
ibha#28 (CHEBI:79359) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#28 (CHEBI:79359) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#28 (CHEBI:79359) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#28 (CHEBI:79359) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#28 (CHEBI:79359) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,15R)-15-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyhexadecanoic acid
Synonyms  Source
3R-hydroxy-15R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acidSMID
(3R,15R)-15-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxypalmitic acidChEBI
3R-hydroxy-15R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-palmitic acidChEBI
Manual XrefsDatabases
ibha%2328%0DSMID
Registry NumbersSources
Reaxys:22233532Reaxys
CAS:1355683-34-9SMID
Citations