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CHEBI:78851 - ascr#13

ChEBI IDCHEBI:78851
ChEBI Nameascr#13
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,6R)-6-hydroxyhept-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC14H24O6
Net Charge0
Average Mass288.340
Monoisotopic Mass288.15729
SMILESC[C@H](CCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C14H24O6/c1-9(6-4-3-5-7-13(17)18)19-14-12(16)8-11(15)10(2)20-14/h5,7,9-12,14-16H,3-4,6,8H2,1-2H3,(H,17,18)/b7-5+/t9-,10+,11-,12-,14-/m1/s1
InChIKeyOZXQOEFFYWNZJI-UYWLPYIRSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Absent in daf-22(ok693) 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#13 (CHEBI:78851) has functional parent (2E,7R)-7-hydroxyoct-2-enoic acid (CHEBI:78850)
ascr#13 (CHEBI:78851) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#13 (CHEBI:78851) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#13 (CHEBI:78851) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#13 (CHEBI:78851) is conjugate acid of ascr#13(1-) (CHEBI:139624)
Incoming Relation(s)
ascr#13(1-) (CHEBI:139624) is conjugate base of ascr#13 (CHEBI:78851)
IUPAC Name 
(2E,7R)-7-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]oct-2-enoic acid
Synonyms  Source
7R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-octenoic acidSMID
asc-ΔC8ChEBI
Manual XrefsDatabases
ascr%2313%0DSMID
Registry NumbersSources
Reaxys:22233389Reaxys
CAS:1355681-45-6SMID
Citations