CHEBI:78745 - icas#20

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ChEBI Name icas#20
ChEBI ID CHEBI:78745
Definition A 4-O-(1H-indol-3-ylcarbonyl)ascaroside derived from (11R)-11-hydroxylauric acid. It is a metabolite of the nematode Caenorhabditis elegans.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H39NO7
Net Charge 0
Average Mass 489.60110
Monoisotopic Mass 489.27265
InChI InChI=1S/C27H39NO7/c1-18(12-8-6-4-3-5-7-9-15-25(30)31)33-27-23(29)16-24(19(2)34-27)35-26(32)21-17-28-22-14-11-10-13-20(21)22/h10-11,13-14,17-19,23-24,27-29H,3-9,12,15-16H2,1-2H3,(H,30,31)/t18-,19+,23-,24-,27-/m1/s1
InChIKey AFPJDDPSVYDRDB-DRONAGRDSA-N
SMILES C[C@H](CCCCCCCCCC(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 dhs28(hj8), acox-1(ok2257), 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 )
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ChEBI Ontology
Outgoing icas#20 (CHEBI:78745) has functional parent (11R)-11-hydroxylauric acid (CHEBI:78978)
icas#20 (CHEBI:78745) has functional parent ascr#20 (CHEBI:78958)
icas#20 (CHEBI:78745) has role Caenorhabditis elegans metabolite (CHEBI:78804)
icas#20 (CHEBI:78745) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
icas#20 (CHEBI:78745) is a 4-O-(1H-indol-3-ylcarbonyl)ascaroside (CHEBI:79024)
icas#20 (CHEBI:78745) is a monocarboxylic acid (CHEBI:25384)
Incoming ibha#20 (CHEBI:79355) has functional parent icas#20 (CHEBI:78745)
IUPAC Name
(11R)-11-[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyloxy]dodecanoic acid
Synonyms Sources
(11R)-11-({(2R,3R,5R,6S)-3-hydroxy-5-[(1H-indol-3-ylcarbonyl)oxy]-6-methyltetrahydro-2H-pyran-2-yl}oxy)dodecanoic acid IUPAC
(11R)-11-[3,6-dideoxy-4-O-(1H-indol-3-ylcarbonyl)-α-L-arabino-hexopyranosyloxy]lauric acid ChEBI
11R-(3'R-hydroxy-5'R-O-(1H-indol-3-ylcarbonyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acid SMID
Manual Xref Database
icas%2320%0D SMID
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Registry Numbers Types Sources
1355683-09-8 CAS Registry Number SMID
22233501 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014