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CHEBI:78972 - ascr#34

ChEBI IDCHEBI:78972
ChEBI Nameascr#34
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (18R)-18-hydroxynonadecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC25H48O6
Net Charge0
Average Mass444.653
Monoisotopic Mass444.34509
SMILESC[C@H](CCCCCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C25H48O6/c1-20(30-25-23(27)19-22(26)21(2)31-25)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-24(28)29/h20-23,25-27H,3-19H2,1-2H3,(H,28,29)/t20-,21+,22-,23-,25-/m1/s1
InChIKeyCGDGMTQYHSCWOZ-FYEJASGKSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8), acox-1(ok2257), and maoc-1(hj13) mutant worms. Ascr#34 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#34 (CHEBI:78972) has functional parent (18R)-18-hydroxynonadecanoic acid (CHEBI:79011)
ascr#34 (CHEBI:78972) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#34 (CHEBI:78972) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#34 (CHEBI:78972) is a monocarboxylic acid (CHEBI:25384)
ascr#34 (CHEBI:78972) is conjugate acid of ascr#34(1-) (CHEBI:139690)
Incoming Relation(s)
bhas#34 (CHEBI:79237) has functional parent ascr#34 (CHEBI:78972)
ascr#34(1-) (CHEBI:139690) is conjugate base of ascr#34 (CHEBI:78972)
IUPAC Name 
(18R)-18-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]nonadecanoic acid
Synonym  Source
18R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonadecanoic acidSMID
Manual XrefsDatabases
ascr%2334%0DSMID
Registry NumbersSources
Reaxys:22233490Reaxys
CAS:1355681-83-2SMID
Citations