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CHEBI:79223 - bhas#10

ChEBI IDCHEBI:79223
ChEBI Namebhas#10
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside that is ascr#10 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 as well as the sour paste nematode, Panagrellus redivivus.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC15H28O7
Net Charge0
Average Mass320.382
Monoisotopic Mass320.18350
SMILESC[C@H](CCCC[C@@H](O)CC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C15H28O7/c1-9(5-3-4-6-11(16)7-14(19)20)21-15-13(18)8-12(17)10(2)22-15/h9-13,15-18H,3-8H2,1-2H3,(H,19,20)/t9-,10+,11-,12-,13-,15-/m1/s1
InChIKeyWNUSOZJRAZSLBP-AOWZIMASSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) mutants and small amounts in acox-1(ok2257) mutant C. elegans.
Panagrellus redivivus (ncbitaxon:6233) - PubMed (23213209) Produced by female
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#10 (CHEBI:79223) has functional parent (3R,8R)-3,8-dihydroxynonanoic acid (CHEBI:79224)
bhas#10 (CHEBI:79223) has functional parent ascr#10 (CHEBI:78838)
bhas#10 (CHEBI:79223) has role Caenorhabditis elegans metabolite (CHEBI:78804)
bhas#10 (CHEBI:79223) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
bhas#10 (CHEBI:79223) is a 3-hydroxy carboxylic acid (CHEBI:61355)
bhas#10 (CHEBI:79223) is a monocarboxylic acid (CHEBI:25384)
bhas#10 (CHEBI:79223) is conjugate acid of bhas#10(1-) (CHEBI:139719)
Incoming Relation(s)
ibha#10 (CHEBI:79334) has functional parent bhas#10 (CHEBI:79223)
bhas#10(1-) (CHEBI:139719) is conjugate base of bhas#10 (CHEBI:79223)
IUPAC Name 
(3R,8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]-3-hydroxynonanoic acid
Synonym  Source
3R-hydroxy-8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acidSMID
Manual XrefsDatabases
bhas%2310%0DSMID
Registry NumbersSources
Reaxys:22233403Reaxys
CAS:1355682-49-3SMID
Citations