oscr#18 (CHEBI:79140)

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ChEBI Name	oscr#18

ChEBI ID	CHEBI:79140

Definition	An ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 11-hydroxyundecanoic 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

C17H32O6

Net Charge

Average Mass

332.43240

Monoisotopic Mass

332.21989

InChI

InChI=1S/C17H32O6/c1-13-14(18)12-15(19)17(23-13)22-11-9-7-5-3-2-4-6-8-10-16(20)21/h13-15,17-19H,2-12H2,1H3,(H,20,21)/t13-,14+,15+,17+/m0/s1

InChIKey

GEMAYWCAMMUVTD-KLZNWCGWSA-N

SMILES

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

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	Detected in wild type (N2) worms. It is a major ascaroside in acox-1(ok2257) mutant worms, and has also been detected in maoc-1(hj13) 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#18 (CHEBI:79140) has functional parent 11-hydroxyundecanoic acid (CHEBI:79126) oscr#18 (CHEBI:79140) has role Caenorhabditis elegans metabolite (CHEBI:78804) oscr#18 (CHEBI:79140) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204) oscr#18 (CHEBI:79140) is a monocarboxylic acid (CHEBI:25384) oscr#18 (CHEBI:79140) is conjugate acid of oscr#18(1−) (CHEBI:139987)

Incoming	bhos#18 (CHEBI:79259) has functional parent oscr#18 (CHEBI:79140) icos#18 (CHEBI:79124) has functional parent oscr#18 (CHEBI:79140) oscr#18-CoA (CHEBI:139988) has functional parent oscr#18 (CHEBI:79140) oscr#18(1−) (CHEBI:139987) is conjugate base of oscr#18 (CHEBI:79140)

IUPAC Name

11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]undecanoic acid

Synonym	Source
11-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-undecanoic acid	SMID

Last Modified

01 March 2018