oscr#3 (CHEBI:79131)

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ChEBI Name	oscr#3

ChEBI ID	CHEBI:79131

Definition	An ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-9-hydroxynon-2-enoic 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

C15H26O6

Net Charge

Average Mass

302.36330

Monoisotopic Mass

302.17294

InChI

InChI=1S/C15H26O6/c1-11-12(16)10-13(17)15(21-11)20-9-7-5-3-2-4-6-8-14(18)19/h6,8,11-13,15-17H,2-5,7,9-10H2,1H3,(H,18,19)/b8-6+/t11-,12+,13+,15+/m0/s1

InChIKey

CYRZSEWKKCHVSI-XHDDSBKUSA-N

SMILES

C[C@@H]1O[C@@H](OCCCCCC\C=C\C(O)=O)[C@H](O)C[C@H]1O

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	Detected in maoc-1(hj13) and acox-1(ok2257) 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#3 (CHEBI:79131) has functional parent (2E)-9-hydroxynon-2-enoic acid (CHEBI:79115) oscr#3 (CHEBI:79131) has role Caenorhabditis elegans metabolite (CHEBI:78804) oscr#3 (CHEBI:79131) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) oscr#3 (CHEBI:79131) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204) oscr#3 (CHEBI:79131) is conjugate acid of oscr#3(1−) (CHEBI:140025)

Incoming	icos#3 (CHEBI:79114) has functional parent oscr#3 (CHEBI:79131) oscr#3-CoA (CHEBI:140053) has functional parent oscr#3 (CHEBI:79131) oscr#3(1−) (CHEBI:140025) is conjugate base of oscr#3 (CHEBI:79131)

IUPAC Name

(2E)-9-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]non-2-enoic acid

Synonym	Source
9-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-nonenoic acid	SMID

Citation	Type	Source
22239548	PubMed citation	Europe PMC

Last Modified

19 February 2018