oscr#22 (CHEBI:79144)

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ChEBI Name	oscr#22

ChEBI ID	CHEBI:79144

Definition	An ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 13-hydroxytridecanoic 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

Download	Molfile XML SDF

Formula

C19H36O6

Net Charge

Average Mass

360.48550

Monoisotopic Mass

360.25119

InChI

InChI=1S/C19H36O6/c1-15-16(20)14-17(21)19(25-15)24-13-11-9-7-5-3-2-4-6-8-10-12-18(22)23/h15-17,19-21H,2-14H2,1H3,(H,22,23)/t15-,16+,17+,19+/m0/s1

InChIKey

BMAOWSPJJLOKGM-DODZYUBVSA-N

SMILES

C[C@@H]1O[C@@H](OCCCCCCCCCCCCC(O)=O)[C@H](O)C[C@H]1O

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	Detected in wild type (N2) and 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 )

ChEBI Ontology
Outgoing	oscr#22 (CHEBI:79144) has functional parent 13-hydroxytridecanoic acid (CHEBI:79166) oscr#22 (CHEBI:79144) has role Caenorhabditis elegans metabolite (CHEBI:78804) oscr#22 (CHEBI:79144) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204) oscr#22 (CHEBI:79144) is a monocarboxylic acid (CHEBI:25384) oscr#22 (CHEBI:79144) is conjugate acid of oscr#22(1−) (CHEBI:140001)

Incoming	bhos#22 (CHEBI:79261) has functional parent oscr#22 (CHEBI:79144) oscr#22-CoA (CHEBI:140002) has functional parent oscr#22 (CHEBI:79144) oscr#22(1−) (CHEBI:140001) is conjugate base of oscr#22 (CHEBI:79144)

IUPAC Name

13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tridecanoic acid

Synonym	Source
13-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-tridecanoic acid	SMID

Citation	Type	Source
22239548	PubMed citation	Europe PMC

Last Modified

23 February 2018