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CHEBI:79233 - bhas#26

ChEBI IDCHEBI:79233
ChEBI Namebhas#26
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#26 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
FormulaC21H40O7
Net Charge0
Average Mass404.544
Monoisotopic Mass404.27740
SMILESC[C@H](CCCCCCCCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C21H40O7/c1-15(27-21-19(24)14-18(23)16(2)28-21)11-9-7-5-3-4-6-8-10-12-17(22)13-20(25)26/h15-19,21-24H,3-14H2,1-2H3,(H,25,26)/t15-,16+,17-,18-,19-,21-/m1/s1
InChIKeyWDFCEBWMCPQIFZ-XBIRKDKFSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) as well as maoc-1(hj13) and acox-1(ok2257) mutant worms. It is a major ascaroside in dhs-28(hj8) 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#26 (CHEBI:79233) has functional parent (3R,14R)-3,14-dihydroxypentadecanoic acid (CHEBI:79247)
bhas#26 (CHEBI:79233) has functional parent ascr#26 (CHEBI:78964)
bhas#26 (CHEBI:79233) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#26 (CHEBI:79233) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#26 (CHEBI:79233) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#26 (CHEBI:79233) is a monocarboxylic acid (CHEBI:25384)
bhas#26 (CHEBI:79233) is conjugate acid of bhas#26(1-) (CHEBI:139747)
Incoming Relation(s)
ibha#26 (CHEBI:79358) has functional parent bhas#26 (CHEBI:79233)
bhas#26(1-) (CHEBI:139747) is conjugate base of bhas#26 (CHEBI:79233)
IUPAC Name 
(3R,14R)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxypentadecanoic acid
Synonym  Source
3R-hydroxy-14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acidSMID
Manual XrefsDatabases
bhas%2326%0DSMID
Registry NumbersSources
Reaxys:22233456Reaxys
CAS:1355682-58-4SMID
Citations