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CHEBI:78958 - ascr#20

ChEBI IDCHEBI:78958
ChEBI Nameascr#20
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (11R)-11-hydroxylauric acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H34O6
Net Charge0
Average Mass346.464
Monoisotopic Mass346.23554
SMILESC[C@H](CCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C18H34O6/c1-13(23-18-16(20)12-15(19)14(2)24-18)10-8-6-4-3-5-7-9-11-17(21)22/h13-16,18-20H,3-12H2,1-2H3,(H,21,22)/t13-,14+,15-,16-,18-/m1/s1
InChIKeySNWMNYQPRXIDAR-ORDFZIBCSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and 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#20 (CHEBI:78958) has functional parent (11R)-11-hydroxylauric acid (CHEBI:78978)
ascr#20 (CHEBI:78958) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#20 (CHEBI:78958) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#20 (CHEBI:78958) is a monocarboxylic acid (CHEBI:25384)
ascr#20 (CHEBI:78958) is conjugate acid of ascr#20(1-) (CHEBI:139647)
Incoming Relation(s)
bhas#20 (CHEBI:79230) has functional parent ascr#20 (CHEBI:78958)
glas#20 (CHEBI:79304) has functional parent ascr#20 (CHEBI:78958)
icas#20 (CHEBI:78745) has functional parent ascr#20 (CHEBI:78958)
ascr#20(1-) (CHEBI:139647) is conjugate base of ascr#20 (CHEBI:78958)
IUPAC Name 
(11R)-11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]dodecanoic acid
Synonyms  Source
11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acidSMID
11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acidChEBI
(11R)-11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]lauric acidChEBI
Manual XrefsDatabases
ascr%2320%0DSMID
Registry NumbersSources
Reaxys:22233413Reaxys
CAS:1355681-57-0SMID
Citations