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CHEBI:79321 - hbas#3

ChEBI IDCHEBI:79321
ChEBI Namehbas#3
Stars
DefinitionA 4-O-(p-hydroxybenzoyl)ascaroside derived from (2E,8R)-8-hydroxynon-2-enoic acid. It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H30O8
Net Charge0
Average Mass422.474
Monoisotopic Mass422.19407
SMILESC[C@H](CCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](OC(=O)c2ccc(O)cc2)C[C@H]1O
InChIInChI=1S/C22H30O8/c1-14(7-5-3-4-6-8-20(25)26)28-22-18(24)13-19(15(2)29-22)30-21(27)16-9-11-17(23)12-10-16/h6,8-12,14-15,18-19,22-24H,3-5,7,13H2,1-2H3,(H,25,26)/b8-6+/t14-,15+,18-,19-,22-/m1/s1
InChIKeyBJUWUCQZCXGYNI-NJABCCJWSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type 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)
hbas#3 (CHEBI:79321) has functional parent (2E,8R)-8-hydroxynon-2-enoic acid (CHEBI:78819)
hbas#3 (CHEBI:79321) has functional parent ascr#3 (CHEBI:78821)
hbas#3 (CHEBI:79321) has role Caenorhabditis elegans metabolite (CHEBI:78804)
hbas#3 (CHEBI:79321) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
hbas#3 (CHEBI:79321) is a 4-O-(p-hydroxybenzoyl)ascaroside (CHEBI:79320)
hbas#3 (CHEBI:79321) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
IUPAC Name 
(2E,8R)-8-{[3,6-dideoxy-4-O-(4-hydroxybenzoyl)-α-L-arabino-hexopyranosyl]oxy}non-2-enoic acid
Synonym  Source
8R-(3'R-hydroxy-5'R-O-(4-hydroxybenzoyl)-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acidSMID
Manual XrefsDatabases
hbas%233SMID
Registry NumbersSources
Reaxys:22233441Reaxys
CAS:1355681-25-2SMID
Citations