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CHEBI:79355 - ibha#20

Default Structure
ChEBI IDCHEBI:79355
ChEBI Nameibha#20
Stars
DefinitionA 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#20 in which the pro-R hydrogen β to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H39NO8
Net Charge0
Average Mass505.608
Monoisotopic Mass505.26757
SMILESC[C@H](CCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2cnc3ccccc23)C[C@H]1O
InChIInChI=1S/C27H39NO8/c1-17(10-6-4-3-5-7-11-19(29)14-25(31)32)34-27-23(30)15-24(18(2)35-27)36-26(33)21-16-28-22-13-9-8-12-20(21)22/h8-9,12-13,16-19,23-24,27-30H,3-7,10-11,14-15H2,1-2H3,(H,31,32)/t17-,18+,19-,23-,24-,27-/m1/s1
InChIKeyGSHRJJXEZKTUHX-WGCTWHLSSA-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#20 (CHEBI:79355) has functional parent (3R,11R)-3,11-dihydroxylauric acid (CHEBI:79243)
ibha#20 (CHEBI:79355) has functional parent bhas#20 (CHEBI:79230)
ibha#20 (CHEBI:79355) has functional parent icas#20 (CHEBI:78745)
ibha#20 (CHEBI:79355) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#20 (CHEBI:79355) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#20 (CHEBI:79355) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#20 (CHEBI:79355) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#20 (CHEBI:79355) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name 
(3R,11R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydodecanoic acid
Synonyms  Source
(3R,11R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxylauric acidChEBI
3R-hydroxy-11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
3R-hydroxy-11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acidChEBI
Manual XrefsDatabases
ibha%2320SMID
Registry NumbersSources
Reaxys:22233514Reaxys
CAS:1355683-26-9SMID
Citations