CHEBI:79353 - ibha#16

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ChEBI Name ibha#16
ChEBI ID CHEBI:79353
Definition A 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#16 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 C25H35NO8
Net Charge 0
Average Mass 477.54730
Monoisotopic Mass 477.23627
InChI InChI=1S/C25H35NO8/c1-15(8-4-3-5-9-17(27)12-23(29)30)32-25-21(28)13-22(16(2)33-25)34-24(31)19-14-26-20-11-7-6-10-18(19)20/h6-7,10-11,14-17,21-22,25-28H,3-5,8-9,12-13H2,1-2H3,(H,29,30)/t15-,16+,17-,21-,22-,25-/m1/s1
InChIKey KNTSMTUFIKIJQO-JUYTZFGZSA-N
SMILES C[C@H](CCCCC[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#16 (CHEBI:79353) has functional parent (3R,9R)-3,9-dihydroxydecanoic acid (CHEBI:79228)
ibha#16 (CHEBI:79353) has functional parent bhas#16 (CHEBI:79227)
ibha#16 (CHEBI:79353) has functional parent icas#16 (CHEBI:79094)
ibha#16 (CHEBI:79353) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#16 (CHEBI:79353) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#16 (CHEBI:79353) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#16 (CHEBI:79353) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#16 (CHEBI:79353) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R,9R)-9-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydecanoic acid
Synonym Source
3R-hydroxy-9R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acid SMID
Manual Xref Database
ibha%2316%0D SMID
View more database links
Registry Numbers Types Sources
1355683-39-4 CAS Registry Number SMID
22233496 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014