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CHEBI:78968 - ascr#30

ChEBI IDCHEBI:78968
ChEBI Nameascr#30
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (16R)-16-hydroxymargaric acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC23H44O6
Net Charge0
Average Mass416.599
Monoisotopic Mass416.31379
SMILESC[C@H](CCCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C23H44O6/c1-18(28-23-21(25)17-20(24)19(2)29-23)15-13-11-9-7-5-3-4-6-8-10-12-14-16-22(26)27/h18-21,23-25H,3-17H2,1-2H3,(H,26,27)/t18-,19+,20-,21-,23-/m1/s1
InChIKeyXIVYAVYHUZLGIV-AIDNLNPPSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms and acox-1(ok2257), dhs-28(hj8), and maoc-1(hj13) mutant worms. Ascr#30 is a major ascaroside in daf-22(ok693) 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#30 (CHEBI:78968) has functional parent (16R)-16-hydroxymargaric acid (CHEBI:79001)
ascr#30 (CHEBI:78968) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#30 (CHEBI:78968) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#30 (CHEBI:78968) is a monocarboxylic acid (CHEBI:25384)
ascr#30 (CHEBI:78968) is conjugate acid of ascr#30(1-) (CHEBI:139678)
Incoming Relation(s)
bhas#30 (CHEBI:79235) has functional parent ascr#30 (CHEBI:78968)
ascr#30(1-) (CHEBI:139678) is conjugate base of ascr#30 (CHEBI:78968)
IUPAC Name 
(16R)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]heptadecanoic acid
Synonym  Source
16R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-heptadecanoic acidSMID
Manual XrefsDatabases
ascr%2330%0DSMID
Registry NumbersSources
Reaxys:22233460Reaxys
CAS:1355681-75-2SMID
Citations