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CHEBI:79237 - bhas#34

ChEBI IDCHEBI:79237
ChEBI Namebhas#34
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#34 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
FormulaC25H48O7
Net Charge0
Average Mass460.652
Monoisotopic Mass460.34000
SMILESC[C@H](CCCCCCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C25H48O7/c1-19(31-25-23(28)18-22(27)20(2)32-25)15-13-11-9-7-5-3-4-6-8-10-12-14-16-21(26)17-24(29)30/h19-23,25-28H,3-18H2,1-2H3,(H,29,30)/t19-,20+,21-,22-,23-,25-/m1/s1
InChIKeyPRXKHETUIWVNNB-MYSWHGEBSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) A major ascaroside detected in dhs-28(hj8), daf-22(ok693), 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#34 (CHEBI:79237) has functional parent (3R,18R)-3,18-dihydroxynonadecanoic acid (CHEBI:79251)
bhas#34 (CHEBI:79237) has functional parent ascr#34 (CHEBI:78972)
bhas#34 (CHEBI:79237) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#34 (CHEBI:79237) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#34 (CHEBI:79237) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#34 (CHEBI:79237) is a monocarboxylic acid (CHEBI:25384)
bhas#34 (CHEBI:79237) is conjugate acid of bhas#34(1-) (CHEBI:139759)
Incoming Relation(s)
bhas#34(1-) (CHEBI:139759) is conjugate base of bhas#34 (CHEBI:79237)
IUPAC Name 
(3R,18R)-18-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxynonadecanoic acid
Synonym  Source
3R-hydroxy-18R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonadecanoic acidSMID
Manual XrefsDatabases
bhas%2334%0DSMID
Registry NumbersSources
Reaxys:22233502Reaxys
CAS:1355682-66-4SMID
Citations