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CHEBI:79238 - bhas#36

ChEBI IDCHEBI:79238
ChEBI Namebhas#36
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#36 in which the pro-R hydrogen that is β to the carboxy group is replaced by a hydroxy group. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC26H50O7
Net Charge0
Average Mass474.679
Monoisotopic Mass474.35565
SMILESC[C@H](CCCCCCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C26H50O7/c1-20(32-26-24(29)19-23(28)21(2)33-26)16-14-12-10-8-6-4-3-5-7-9-11-13-15-17-22(27)18-25(30)31/h20-24,26-29H,3-19H2,1-2H3,(H,30,31)/t20-,21+,22-,23-,24-,26-/m1/s1
InChIKeySJIIOKVLMUJXBB-VFRMFGFGSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) A major ascaroside in daf-22(ok693) mutant worms, also detected in dhs-28(hj8) 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)
bhas#36 (CHEBI:79238) has functional parent (3R,19R)-19-dihydroxyicosanoic acid (CHEBI:79252)
bhas#36 (CHEBI:79238) has functional parent ascr#36 (CHEBI:78974)
bhas#36 (CHEBI:79238) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#36 (CHEBI:79238) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#36 (CHEBI:79238) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#36 (CHEBI:79238) is a monocarboxylic acid (CHEBI:25384)
bhas#36 (CHEBI:79238) is conjugate acid of bhas#36(1-) (CHEBI:139762)
Incoming Relation(s)
bhas#36(1-) (CHEBI:139762) is conjugate base of bhas#36 (CHEBI:79238)
IUPAC Name 
(3R,19R)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyicosanoic acid
Synonyms  Source
3R-hydroxy-19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-icosanoic acidSMID
(3R,19R)-19-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxyeicosanoic acidChEBI
3R-hydroxy-19R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-eicosanoic acidChEBI
Manual XrefsDatabases
bhas%2336%0DSMID
Registry NumbersSources
Reaxys:22233518Reaxys
CAS:1355682-68-6SMID
Citations