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CHEBI:79149 - oscr#27

ChEBI IDCHEBI:79149
ChEBI Nameoscr#27
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-16-hydroxyhexadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H40O6
Net Charge0
Average Mass400.556
Monoisotopic Mass400.28249
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C22H40O6/c1-18-19(23)17-20(24)22(28-18)27-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-21(25)26/h13,15,18-20,22-24H,2-12,14,16-17H2,1H3,(H,25,26)/b15-13+/t18-,19+,20+,22+/m0/s1
InChIKeyBEKLYIAFACFFDO-UPBMBJRSSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in maoc-1(hj13), and dhs-28(hj8) 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)
oscr#27 (CHEBI:79149) has functional parent (2E)-16-hydroxyhexadec-2-enoic acid (CHEBI:79170)
oscr#27 (CHEBI:79149) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#27 (CHEBI:79149) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#27 (CHEBI:79149) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#27 (CHEBI:79149) is conjugate acid of oscr#27(1−) (CHEBI:140016)
Incoming Relation(s)
oscr#27-CoA (CHEBI:140017) has functional parent oscr#27 (CHEBI:79149)
oscr#27(1−) (CHEBI:140016) is conjugate base of oscr#27 (CHEBI:79149)
IUPAC Name 
(2E)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadec-2-enoic acid
Synonym  Source
16-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-hexadecenoic acidSMID
Manual XrefsDatabases
oscr%2327SMID
Registry NumbersSources
Reaxys:22233447Reaxys
CAS:1355682-27-7SMID
Citations