EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:79150 - oscr#28

ChEBI IDCHEBI:79150
ChEBI Nameoscr#28
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 16-hydroxyhexadecanoic acid (also known as juniperic acid) with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified23 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H42O6
Net Charge0
Average Mass402.572
Monoisotopic Mass402.29814
SMILESC[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C22H42O6/c1-18-19(23)17-20(24)22(28-18)27-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-21(25)26/h18-20,22-24H,2-17H2,1H3,(H,25,26)/t18-,19+,20+,22+/m0/s1
InChIKeyRARJQAOGTFMPFZ-GPQLQYNLSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in acox-1(ok2257), maoc-1(hj13), daf-22(ok693), and 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)
oscr#28 (CHEBI:79150) has functional parent 16-hydroxyhexadecanoic acid (CHEBI:55328)
oscr#28 (CHEBI:79150) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#28 (CHEBI:79150) is a monocarboxylic acid (CHEBI:25384)
oscr#28 (CHEBI:79150) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#28 (CHEBI:79150) is conjugate acid of oscr#28(1−) (CHEBI:140019)
Incoming Relation(s)
bhos#28 (CHEBI:79264) has functional parent oscr#28 (CHEBI:79150)
oscr#28-CoA (CHEBI:140020) has functional parent oscr#28 (CHEBI:79150)
oscr#28(1−) (CHEBI:140019) is conjugate base of oscr#28 (CHEBI:79150)
IUPAC Name 
16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadecanoic acid
Synonym  Source
16-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acidSMID
Manual XrefsDatabases
oscr%2328SMID
Registry NumbersSources
Reaxys:22233457Reaxys
CAS:1355682-29-9SMID
Citations