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CHEBI:78969 - ascr#31

ChEBI IDCHEBI:78969
ChEBI Nameascr#31
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,17R)-17-hydroxyoctadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC24H44O6
Net Charge0
Average Mass428.610
Monoisotopic Mass428.31379
SMILESC[C@H](CCCCCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C24H44O6/c1-19(29-24-22(26)18-21(25)20(2)30-24)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-23(27)28/h15,17,19-22,24-26H,3-14,16,18H2,1-2H3,(H,27,28)/b17-15+/t19-,20+,21-,22-,24-/m1/s1
InChIKeyAUKDJCIZWSIDEC-QGKNABGUSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Found 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#31 (CHEBI:78969) has functional parent (2E,17R)-17-hydroxyoctadec-2-enoic acid (CHEBI:79002)
ascr#31 (CHEBI:78969) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#31 (CHEBI:78969) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#31 (CHEBI:78969) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#31 (CHEBI:78969) is conjugate acid of ascr#31(1-) (CHEBI:139681)
Incoming Relation(s)
ascr#31(1-) (CHEBI:139681) is conjugate base of ascr#31 (CHEBI:78969)
IUPAC Name 
(2E,17R)-17-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]octadec-2-enoic acid
Synonym  Source
17R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-octadecenoic acidSMID
Manual XrefsDatabases
ascr%2331%0DSMID
Registry NumbersSources
Reaxys:22233468Reaxys
CAS:1355681-77-4SMID
Citations