ascr#13 (CHEBI:78851)

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ChEBI Name	ascr#13

ChEBI ID	CHEBI:78851

Definition	An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,6R)-6-hydroxyhept-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

C14H24O6

Net Charge

Average Mass

288.33680

Monoisotopic Mass

288.15729

InChI

InChI=1S/C14H24O6/c1-9(6-4-3-5-7-13(17)18)19-14-12(16)8-11(15)10(2)20-14/h5,7,9-12,14-16H,3-4,6,8H2,1-2H3,(H,17,18)/b7-5+/t9-,10+,11-,12-,14-/m1/s1

InChIKey

OZXQOEFFYWNZJI-UYWLPYIRSA-N

SMILES

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

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	Absent in daf-22(ok693) 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	ascr#13 (CHEBI:78851) has functional parent (2E,7R)-7-hydroxyoct-2-enoic acid (CHEBI:78850) ascr#13 (CHEBI:78851) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#13 (CHEBI:78851) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) ascr#13 (CHEBI:78851) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#13 (CHEBI:78851) is conjugate acid of ascr#13(1-) (CHEBI:139624)

Incoming	ascr#13(1-) (CHEBI:139624) is conjugate base of ascr#13 (CHEBI:78851)

IUPAC Name

(2E,7R)-7-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]oct-2-enoic acid

Synonyms	Sources
7R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-octenoic acid	SMID
asc-ΔC8	ChEBI

Citation	Type	Source
22239548	PubMed citation	Europe PMC

Last Modified

24 July 2014