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CHEBI:78971 - ascr#33

ChEBI IDCHEBI:78971
ChEBI Nameascr#33
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,18R)-18-hydroxynonadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H46O6
Net Charge0
Average Mass442.637
Monoisotopic Mass442.32944
SMILESC[C@H](CCCCCCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C25H46O6/c1-20(30-25-23(27)19-22(26)21(2)31-25)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-24(28)29/h16,18,20-23,25-27H,3-15,17,19H2,1-2H3,(H,28,29)/b18-16+/t20-,21+,22-,23-,25-/m1/s1
InChIKeyJQBYGLLYFPDQJA-NVJHKYEUSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) and maoc-1(hj13) 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#33 (CHEBI:78971) has functional parent (2E,18R)-18-hydroxynonadec-2-enoic acid (CHEBI:79006)
ascr#33 (CHEBI:78971) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#33 (CHEBI:78971) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#33 (CHEBI:78971) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#33 (CHEBI:78971) is conjugate acid of ascr#33(1-) (CHEBI:139687)
Incoming Relation(s)
ascr#33(1-) (CHEBI:139687) is conjugate base of ascr#33 (CHEBI:78971)
IUPAC Name 
(2E,18R)-18-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]nonadec-2-enoic acid
Synonym  Source
18R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonadecenoic acidSMID
Manual XrefsDatabases
ascr%2333%0DSMID
Registry NumbersSources
Reaxys:22233480Reaxys
CAS:1355681-81-0SMID
Citations