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CHEBI:78955 - ascr#18

ChEBI IDCHEBI:78955
ChEBI Nameascr#18
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (10R)-10-hydroxyundecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H32O6
Net Charge0
Average Mass332.437
Monoisotopic Mass332.21989
SMILESC[C@H](CCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C17H32O6/c1-12(9-7-5-3-4-6-8-10-16(20)21)22-17-15(19)11-14(18)13(2)23-17/h12-15,17-19H,3-11H2,1-2H3,(H,20,21)/t12-,13+,14-,15-,17-/m1/s1
InChIKeyAHRWSOYISAIFOZ-JRBZFYFNSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and dhs-28(hj8) and maoc-1(hj13) mutant worms. A major ascaroside in acox-1(ok2257) mutant worms.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
ascr#18 (CHEBI:78955) has functional parent (10R)-10-hydroxyundecanoic acid (CHEBI:78956)
ascr#18 (CHEBI:78955) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#18 (CHEBI:78955) is a monocarboxylic acid (CHEBI:25384)
ascr#18 (CHEBI:78955) is conjugate acid of ascr#18(1−) (CHEBI:139639)
Incoming Relation(s)
bhas#18 (CHEBI:79229) has functional parent ascr#18 (CHEBI:78955)
glas#18 (CHEBI:79303) has functional parent ascr#18 (CHEBI:78955)
icas#18 (CHEBI:79105) has functional parent ascr#18 (CHEBI:78955)
ascr#18(1−) (CHEBI:139639) is conjugate base of ascr#18 (CHEBI:78955)
IUPAC Name 
(10R)-10-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]undecanoic acid
Synonyms  Source
10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acidSMID
asc-C11ChEBI
Manual XrefsDatabases
ascr%2318%0DSMID
LMFA13040009LIPID MAPS
Registry NumbersSources
Reaxys:22233406Reaxys
Citations