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CHEBI:78962 - ascr#24

ChEBI IDCHEBI:78962
ChEBI Nameascr#24
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (13R)-13-hydroxymyristic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H38O6
Net Charge0
Average Mass374.518
Monoisotopic Mass374.26684
SMILESC[C@H](CCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C20H38O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h15-18,20-22H,3-14H2,1-2H3,(H,23,24)/t15-,16+,17-,18-,20-/m1/s1
InChIKeyNRXYKCLIMLPUIO-KWXDATOUSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in daf-22(ok693), dhs-28(hj8), acox-1(ok2257), and 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#24 (CHEBI:78962) has functional parent (13R)-13-hydroxymyristic acid (CHEBI:78989)
ascr#24 (CHEBI:78962) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#24 (CHEBI:78962) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#24 (CHEBI:78962) is a monocarboxylic acid (CHEBI:25384)
ascr#24 (CHEBI:78962) is conjugate acid of ascr#24(1-) (CHEBI:139659)
Incoming Relation(s)
bhas#24 (CHEBI:79232) has functional parent ascr#24 (CHEBI:78962)
glas#24 (CHEBI:79306) has functional parent ascr#24 (CHEBI:78962)
ascr#24(1-) (CHEBI:139659) is conjugate base of ascr#24 (CHEBI:78962)
IUPAC Name 
(13R)-13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tetradecanoic acid
Synonym  Source
13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tetradecanoic acidSMID
Manual XrefsDatabases
ascr%2324%0DSMID
Registry NumbersSources
Reaxys:22233431Reaxys
CAS:1355681-61-6SMID
Citations