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CHEBI:79143 - oscr#21

ChEBI IDCHEBI:79143
ChEBI Nameoscr#21
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-13-hydroxytridec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified1 March 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H34O6
Net Charge0
Average Mass358.475
Monoisotopic Mass358.23554
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCC/C=C/C(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C19H34O6/c1-15-16(20)14-17(21)19(25-15)24-13-11-9-7-5-3-2-4-6-8-10-12-18(22)23/h10,12,15-17,19-21H,2-9,11,13-14H2,1H3,(H,22,23)/b12-10+/t15-,16+,17+,19+/m0/s1
InChIKeyDEQPIGLSNWHDFR-VATKAKJBSA-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#21 (CHEBI:79143) has functional parent (2E)-13-hydroxytridec-2-enoic acid (CHEBI:79165)
oscr#21 (CHEBI:79143) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#21 (CHEBI:79143) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#21 (CHEBI:79143) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#21 (CHEBI:79143) is conjugate acid of oscr#21(1−) (CHEBI:139998)
Incoming Relation(s)
oscr#21-CoA (CHEBI:139999) has functional parent oscr#21 (CHEBI:79143)
oscr#21(1−) (CHEBI:139998) is conjugate base of oscr#21 (CHEBI:79143)
IUPAC Name 
(2E)-13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridec-2-enoic acid
Synonym  Source
13-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tridecenoic acidSMID
Manual XrefsDatabases
oscr%2321%0DSMID
Registry NumbersSources
Reaxys:22233419Reaxys
CAS:1355682-13-1SMID
Citations