CHEBI:79374 - ibho#22

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ChEBI Name ibho#22
ChEBI ID CHEBI:79374
Definition An ω-hydroxy fatty acid ascaroside that is bhos#22 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 C28H41NO8
Net Charge 0
Average Mass 519.62700
Monoisotopic Mass 519.28322
InChI InChI=1S/C28H41NO8/c1-19-25(37-27(34)22-18-29-23-14-10-9-13-21(22)23)17-24(31)28(36-19)35-15-11-7-5-3-2-4-6-8-12-20(30)16-26(32)33/h9-10,13-14,18-20,24-25,28-31H,2-8,11-12,15-17H2,1H3,(H,32,33)/t19-,20+,24+,25+,28+/m0/s1
InChIKey FUIIPNLIVZGYJM-RHENGWIESA-N
SMILES C[C@@H]1O[C@@H](OCCCCCCCCCC[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#22 (CHEBI:79374) has functional parent (3R)-3,13-dihydroxytridecanoic acid (CHEBI:79279)
ibho#22 (CHEBI:79374) has functional parent bhos#22 (CHEBI:79261)
ibho#22 (CHEBI:79374) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibho#22 (CHEBI:79374) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
ibho#22 (CHEBI:79374) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibho#22 (CHEBI:79374) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibho#22 (CHEBI:79374) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytridecanoic acid
Synonym Source
3R-hydroxy-13-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acid SMID
Manual Xref Database
ibho%2322 SMID
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Registry Numbers Types Sources
1355683-45-2 CAS Registry Number SMID
22233520 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014