CHEBI:79372 - ibho#18

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ChEBI Name ibho#18
ChEBI ID CHEBI:79372
Definition An ω-hydroxy fatty acid ascaroside that is bhos#18 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.
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/c1-17-23(35-25(32)20-16-27-21-12-8-7-11-19(20)21)15-22(29)26(34-17)33-13-9-5-3-2-4-6-10-18(28)14-24(30)31/h7-8,11-12,16-18,22-23,26-29H,2-6,9-10,13-15H2,1H3,(H,30,31)/t17-,18+,22+,23+,26+/m0/s1
InChIKey KNUQGRSJUADXIR-SIHSWOPCSA-N
SMILES C[C@@H]1O[C@@H](OCCCCCCCC[C@@H](O)CC(O)=O)[C@H](O)C[C@H]1OC(=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 ibho#18 (CHEBI:79372) has functional parent (3R)-3,11-dihydroxyundecanoic acid (CHEBI:79275)
ibho#18 (CHEBI:79372) has functional parent bhos#18 (CHEBI:79259)
ibho#18 (CHEBI:79372) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#18 (CHEBI:79372) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
ibho#18 (CHEBI:79372) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#18 (CHEBI:79372) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#18 (CHEBI:79372) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxyundecanoic acid
Synonym Source
3R-hydroxy-11-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acid SMID
Manual Xref Database
ibho%2318 SMID
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Registry Numbers Types Sources
1355683-41-8 CAS Registry Number SMID
22233513 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014