CHEBI:79150 - oscr#28

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ChEBI Name oscr#28
ChEBI ID CHEBI:79150
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H42O6
Net Charge 0
Average Mass 402.56530
Monoisotopic Mass 402.29814
InChI InChI=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
InChIKey RARJQAOGTFMPFZ-GPQLQYNLSA-N
SMILES C[C@@H]1O[C@@H](OCCCCCCCCCCCCCCCC(O)=O)[C@H](O)C[C@H]1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in acox-1(ok2257), maoc-1(hj13), daf-22(ok693), and dhs-28(hj8) mutant worms. See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via hydroxy fatty acid ascaroside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#28 (CHEBI:79150) is a monocarboxylic acid (CHEBI:25384)
oscr#28 (CHEBI:79150) is conjugate acid of oscr#28(1−) (CHEBI:140019)
Incoming 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 acid SMID
Manual Xref Database
oscr%2328 SMID
View more database links
Registry Numbers Types Sources
1355682-29-9 CAS Registry Number SMID
22233457 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
23 February 2018