EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:78967 - ascr#29

ChEBI IDCHEBI:78967
ChEBI Nameascr#29
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,16R)-16-hydroxyheptadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC23H42O6
Net Charge0
Average Mass414.583
Monoisotopic Mass414.29814
SMILESC[C@H](CCCCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C23H42O6/c1-18(28-23-21(25)17-20(24)19(2)29-23)15-13-11-9-7-5-3-4-6-8-10-12-14-16-22(26)27/h14,16,18-21,23-25H,3-13,15,17H2,1-2H3,(H,26,27)/b16-14+/t18-,19+,20-,21-,23-/m1/s1
InChIKeyXUIDIXMFLJXJDI-XUAZKPKSSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Found in dhs-28(hj8), acox-1(ok2257), 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#29 (CHEBI:78967) has functional parent (2E,16R)-16-hydroxyheptadec-2-enoic acid (CHEBI:78999)
ascr#29 (CHEBI:78967) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#29 (CHEBI:78967) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#29 (CHEBI:78967) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#29 (CHEBI:78967) is conjugate acid of ascr#29(1-) (CHEBI:139674)
Incoming Relation(s)
ascr#29(1-) (CHEBI:139674) is conjugate base of ascr#29 (CHEBI:78967)
IUPAC Name 
(2E,16R)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]heptadec-2-enoic acid
Synonym  Source
16R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2EEheptadecenoic acidSMID
Manual XrefsDatabases
ascr%2329%0DSMID
Registry NumbersSources
Reaxys:22233452Reaxys
CAS:1355681-73-0SMID
Citations