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CHEBI:78960 - ascr#22

ChEBI IDCHEBI:78960
ChEBI Nameascr#22
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (12R)-12-hydroxytridecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified5 January 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC19H36O6
Net Charge0
Average Mass360.491
Monoisotopic Mass360.25119
SMILESC[C@H](CCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C19H36O6/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/h14-17,19-21H,3-13H2,1-2H3,(H,22,23)/t14-,15+,16-,17-,19-/m1/s1
InChIKeyLCCMRNZRAPDWCS-FSNPWBFUSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms and daf-22(ok693), dhs-28(hj8), and maoc-1(hj13) mutant worms. A major ascaroside detected 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 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#22 (CHEBI:78960) has functional parent (12R)-12-hydroxytridecanoic acid (CHEBI:78980)
ascr#22 (CHEBI:78960) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#22 (CHEBI:78960) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#22 (CHEBI:78960) is a monocarboxylic acid (CHEBI:25384)
ascr#22 (CHEBI:78960) is conjugate acid of ascr#22(1-) (CHEBI:139653)
Incoming Relation(s)
ascr#22-CoA (CHEBI:139654) has functional parent ascr#22 (CHEBI:78960)
bhas#22 (CHEBI:79231) has functional parent ascr#22 (CHEBI:78960)
glas#22 (CHEBI:79305) has functional parent ascr#22 (CHEBI:78960)
icas#22 (CHEBI:79108) has functional parent ascr#22 (CHEBI:78960)
ascr#22(1-) (CHEBI:139653) is conjugate base of ascr#22 (CHEBI:78960)
IUPAC Name 
(12R)-12-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridecanoic acid
Synonym  Source
12R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acidSMID
Manual XrefsDatabases
ascr%2322%0DSMID
LMFA13040010LIPID MAPS
Registry NumbersSources
Reaxys:22233421Reaxys
CAS:1186217-43-5SMID
Citations