CHEBI:79355 - ibha#20

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ChEBI Name ibha#20
ChEBI ID CHEBI:79355
Definition A 4-O-(1H-indol-3-ylcarbonyl)ascaroside that is icas#20 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 C27H39NO8
Net Charge 0
Average Mass 505.60050
Monoisotopic Mass 505.26757
InChI InChI=1S/C27H39NO8/c1-17(10-6-4-3-5-7-11-19(29)14-25(31)32)34-27-23(30)15-24(18(2)35-27)36-26(33)21-16-28-22-13-9-8-12-20(21)22/h8-9,12-13,16-19,23-24,27-30H,3-7,10-11,14-15H2,1-2H3,(H,31,32)/t17-,18+,19-,23-,24-,27-/m1/s1
InChIKey GSHRJJXEZKTUHX-WGCTWHLSSA-N
SMILES C[C@H](CCCCCCC[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#20 (CHEBI:79355) has functional parent (3R,11R)-3,11-dihydroxylauric acid (CHEBI:79243)
ibha#20 (CHEBI:79355) has functional parent bhas#20 (CHEBI:79230)
ibha#20 (CHEBI:79355) has functional parent icas#20 (CHEBI:78745)
ibha#20 (CHEBI:79355) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ibha#20 (CHEBI:79355) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ibha#20 (CHEBI:79355) is a 3-hydroxy carboxylic acid (CHEBI:61355)
ibha#20 (CHEBI:79355) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
ibha#20 (CHEBI:79355) is a monocarboxylic acid (CHEBI:25384)
IUPAC Name
(3R,11R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxydodecanoic acid
Synonyms Sources
(3R,11R)-11-{[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyl]oxy}-3-hydroxylauric acid ChEBI
3R-hydroxy-11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acid SMID
3R-hydroxy-11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acid ChEBI
Manual Xref Database
ibha%2320 SMID
View more database links
Registry Numbers Types Sources
1355683-26-9 CAS Registry Number SMID
22233514 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014