CHEBI:79354 - ibha#18

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ChEBI Name ibha#18
ChEBI ID CHEBI:79354
Definition A 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#18 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
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Formula C26H37NO8
Net Charge 0
Average Mass 491.57390
Monoisotopic Mass 491.25192
InChI InChI=1S/C26H37NO8/c1-16(9-5-3-4-6-10-18(28)13-24(30)31)33-26-22(29)14-23(17(2)34-26)35-25(32)20-15-27-21-12-8-7-11-19(20)21/h7-8,11-12,15-18,22-23,26-29H,3-6,9-10,13-14H2,1-2H3,(H,30,31)/t16-,17+,18-,22-,23-,26-/m1/s1
InChIKey QHLYWGFFZVVDPY-CRZRSRDBSA-N
SMILES C[C@H](CCCCCC[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#18 (CHEBI:79354) has functional parent (3R,10R)-3,10-dihydroxyundecanoic acid (CHEBI:79242)
ibha#18 (CHEBI:79354) has functional parent bhas#18 (CHEBI:79229)
ibha#18 (CHEBI:79354) has functional parent icas#18 (CHEBI:79105)
ibha#18 (CHEBI:79354) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#18 (CHEBI:79354) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#18 (CHEBI:79354) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#18 (CHEBI:79354) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#18 (CHEBI:79354) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R,10R)-10-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyundecanoic acid
Synonym Source
3R-hydroxy-10R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acid SMID
Manual Xref Database
ibha%2318 SMID
View more database links
Registry Numbers Types Sources
1355683-24-7 CAS Registry Number SMID
22233506 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014