CHEBI:79357 - ibha#24

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ChEBI Name ibha#24
ChEBI ID CHEBI:79357
Definition An (ω−1)-hydroxy fatty acid ascaroside that is bhas#24 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 C29H43NO8
Net Charge 0
Average Mass 533.65360
Monoisotopic Mass 533.29887
InChI InChI=1S/C29H43NO8/c1-19(12-8-6-4-3-5-7-9-13-21(31)16-27(33)34)36-29-25(32)17-26(20(2)37-29)38-28(35)23-18-30-24-15-11-10-14-22(23)24/h10-11,14-15,18-21,25-26,29-32H,3-9,12-13,16-17H2,1-2H3,(H,33,34)/t19-,20+,21-,25-,26-,29-/m1/s1
InChIKey VEGIRKJOIIBEHY-HFAWLSGZSA-N
SMILES C[C@H](CCCCCCCCC[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#24 (CHEBI:79357) has functional parent (3R,13R)-3,13-dihydroxymyristic acid (CHEBI:79245)
ibha#24 (CHEBI:79357) has functional parent bhas#24 (CHEBI:79232)
ibha#24 (CHEBI:79357) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#24 (CHEBI:79357) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#24 (CHEBI:79357) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#24 (CHEBI:79357) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#24 (CHEBI:79357) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R,13R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxytetradecanoic acid
Synonyms Sources
(3R,13R)-13-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxymyristic acid ChEBI
3R-hydroxy-13R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-myristic acid ChEBI
3R-hydroxy-13R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acid SMID
Manual Xref Database
ibha%2324 SMID
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Registry Numbers Types Sources
1355683-30-5 CAS Registry Number SMID
22233524 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014