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CHEBI:78974 - ascr#36

ChEBI IDCHEBI:78974
ChEBI Nameascr#36
Stars
DefinitionAn (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.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H50O6
Net Charge0
Average Mass458.680
Monoisotopic Mass458.36074
SMILESC[C@H](CCCCCCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=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
InChIKeyHXSYLHMSXGUNTO-DHWOPMESSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. It is a major ascaroside in daf-22(ok693) mutant worms.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-eicosanoic acidChEBI
19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-icosanoic acidSMID
(19R)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]eicosanoic acidChEBI
Manual XrefsDatabases
ascr%2336%0DSMID
Registry NumbersSources
Reaxys:22233499Reaxys
CAS:1355681-87-6SMID
Citations