CHEBI:78974 - ascr#36

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ChEBI Name ascr#36
ChEBI ID CHEBI:78974
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (19R)-19-hydroxyicosanoic acid with ascarylopyranose (the α anomer). 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 C26H50O6
Net Charge 0
Average Mass 458.67160
Monoisotopic Mass 458.36074
InChI InChI=1S/C26H50O6/c1-21(31-26-24(28)20-23(27)22(2)32-26)18-16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-19-25(29)30/h21-24,26-28H,3-20H2,1-2H3,(H,29,30)/t21-,22+,23-,24-,26-/m1/s1
InChIKey HXSYLHMSXGUNTO-DHWOPMESSA-N
SMILES C[C@H](CCCCCCCCCCCCCCCCCC(O)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. It is a major ascaroside in daf-22(ok693) 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 ascr#36 (CHEBI:78974) has functional parent (19R)-19-hydroxyicosanoic acid (CHEBI:79015)
ascr#36 (CHEBI:78974) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#36 (CHEBI:78974) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#36 (CHEBI:78974) is a monocarboxylic acid (CHEBI:25384)
ascr#36 (CHEBI:78974) is conjugate acid of ascr#36(1-) (CHEBI:139696)
Incoming bhas#36 (CHEBI:79238) has functional parent ascr#36 (CHEBI:78974)
ascr#36(1-) (CHEBI:139696) is conjugate base of ascr#36 (CHEBI:78974)
IUPAC Name
(19R)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]icosanoic acid
Synonyms Sources
(19R)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]eicosanoic acid ChEBI
19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-eicosanoic acid ChEBI
19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-icosanoic acid SMID
Manual Xref Database
ascr%2336%0D SMID
View more database links
Registry Numbers Types Sources
1355681-87-6 CAS Registry Number SMID
22233499 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014