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CHEBI:78966 - ascr#28

Default Structure
ChEBI IDCHEBI:78966
ChEBI Nameascr#28
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (15R)-15-hydroxypalmitic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H42O6
Net Charge0
Average Mass402.572
Monoisotopic Mass402.29814
SMILESC[C@H](CCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C22H42O6/c1-17(27-22-20(24)16-19(23)18(2)28-22)14-12-10-8-6-4-3-5-7-9-11-13-15-21(25)26/h17-20,22-24H,3-16H2,1-2H3,(H,25,26)/t17-,18+,19-,20-,22-/m1/s1
InChIKeyHSLYPVWJYLQYET-AIYVTKCESA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8), acox-1(ok2257), and maoc-1(hj13) mutant worms and 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#28 (CHEBI:78966) has functional parent (15R)-15-hydroxypalmitic acid (CHEBI:78998)
ascr#28 (CHEBI:78966) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#28 (CHEBI:78966) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#28 (CHEBI:78966) is a monocarboxylic acid (CHEBI:25384)
ascr#28 (CHEBI:78966) is conjugate acid of ascr#28(1-) (CHEBI:139671)
Incoming Relation(s)
bhas#28 (CHEBI:79234) has functional parent ascr#28 (CHEBI:78966)
ascr#28(1-) (CHEBI:139671) is conjugate base of ascr#28 (CHEBI:78966)
IUPAC Name 
(15R)-15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadecanoic acid
Synonym  Source
15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acidSMID
Manual XrefsDatabases
ascr%2328%0DSMID
Registry NumbersSources
Reaxys:22233451Reaxys
CAS:1355681-71-8SMID
Citations