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CHEBI:78959 - ascr#21

ChEBI IDCHEBI:78959
ChEBI Nameascr#21
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,12R)-12-hydroxytridec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified5 January 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H34O6
Net Charge0
Average Mass358.475
Monoisotopic Mass358.23554
SMILESC[C@H](CCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C19H34O6/c1-14(24-19-17(21)13-16(20)15(2)25-19)11-9-7-5-3-4-6-8-10-12-18(22)23/h10,12,14-17,19-21H,3-9,11,13H2,1-2H3,(H,22,23)/b12-10+/t14-,15+,16-,17-,19-/m1/s1
InChIKeyXUGAOOQYBZSMCP-ZXSNAGKJSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) and a major ascaroside detected in 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#21 (CHEBI:78959) has functional parent (2E,12R)-12-hydroxytridec-2-enoic acid (CHEBI:78979)
ascr#21 (CHEBI:78959) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#21 (CHEBI:78959) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#21 (CHEBI:78959) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#21 (CHEBI:78959) is conjugate acid of ascr#21(1-) (CHEBI:139650)
Incoming Relation(s)
ascr#21-CoA (CHEBI:139651) has functional parent ascr#21 (CHEBI:78959)
icas#21 (CHEBI:79107) has functional parent ascr#21 (CHEBI:78959)
ascr#21(1-) (CHEBI:139650) is conjugate base of ascr#21 (CHEBI:78959)
IUPAC Name 
(2E,12R)-12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridec-2-enoic acid
Synonym  Source
12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tridecenoic acidSMID
Manual XrefsDatabases
ascr%2321%0DSMID
Registry NumbersSources
Reaxys:22233420Reaxys
CAS:1355681-13-8Reaxys
CAS:1355681-57-0SMID
Citations