CHEBI:79356 - ibha#22

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ibha#22
ChEBI ID CHEBI:79356
Definition A 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#22 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C28H41NO8
Net Charge 0
Average Mass 519.62700
Monoisotopic Mass 519.28322
InChI InChI=1S/C28H41NO8/c1-18(11-7-5-3-4-6-8-12-20(30)15-26(32)33)35-28-24(31)16-25(19(2)36-28)37-27(34)22-17-29-23-14-10-9-13-21(22)23/h9-10,13-14,17-20,24-25,28-31H,3-8,11-12,15-16H2,1-2H3,(H,32,33)/t18-,19+,20-,24-,25-,28-/m1/s1
InChIKey SUECAIROUVPYHD-JZBHREIRSA-N
SMILES C[C@H](CCCCCCCC[C@@H](O)CC(O)=O)O[C@@H]1O[C@@H](C)[C@@H](C[C@H]1O)OC(=O)c1c[nH]c2ccccc12
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via hydroxy fatty acid ascaroside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ibha#22 (CHEBI:79356) has functional parent (3R,12R)-3,12-dihydroxytridecanoic acid (CHEBI:79244)
ibha#22 (CHEBI:79356) has functional parent bhas#22 (CHEBI:79231)
ibha#22 (CHEBI:79356) has functional parent icas#22 (CHEBI:79108)
ibha#22 (CHEBI:79356) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#22 (CHEBI:79356) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#22 (CHEBI:79356) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#22 (CHEBI:79356) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#22 (CHEBI:79356) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R,12R)-12-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytridecanoic acid
Synonym Source
3R-hydroxy-12R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acid SMID
Manual Xref Database
ibha%2322 SMID
View more database links
Registry Numbers Types Sources
1355683-28-1 CAS Registry Number SMID
22233523 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014