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CHEBI:78970 - ascr#32

ChEBI IDCHEBI:78970
ChEBI Nameascr#32
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (17R)-17-hydroxystearic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC24H46O6
Net Charge0
Average Mass430.626
Monoisotopic Mass430.32944
SMILESC[C@H](CCCCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C24H46O6/c1-19(29-24-22(26)18-21(25)20(2)30-24)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-23(27)28/h19-22,24-26H,3-18H2,1-2H3,(H,27,28)/t19-,20+,21-,22-,24-/m1/s1
InChIKeySRGDNDRZLIZKNJ-AQKHVRLOSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Found in dhs-28(hj8) and maoc-1(hj13) mutant worms. It 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#32 (CHEBI:78970) has functional parent (R)-17-hydroxyoctadecanoic acid (CHEBI:79004)
ascr#32 (CHEBI:78970) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#32 (CHEBI:78970) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#32 (CHEBI:78970) is a monocarboxylic acid (CHEBI:25384)
ascr#32 (CHEBI:78970) is conjugate acid of ascr#32(1-) (CHEBI:139684)
Incoming Relation(s)
bhas#32 (CHEBI:79236) has functional parent ascr#32 (CHEBI:78970)
ascr#32(1-) (CHEBI:139684) is conjugate base of ascr#32 (CHEBI:78970)
IUPAC Name 
(17R)-17-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]octadecanoic acid
Synonym  Source
17R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-octadecanoic acidSMID
Manual XrefsDatabases
ascr%2332%0DSMID
Registry NumbersSources
Reaxys:22233469Reaxys
CAS:1355681-79-6SMID
Citations