ascr#10 (CHEBI:78838)

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ChEBI Name	ascr#10

ChEBI ID	CHEBI:78838

Definition	An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (8R)-8-hydroxynonanoic acid with ascarylopyranose (the α anomer). A metabolite of the nematode Caenorhabditis elegans, it is the direct biosynthetic precursor to ascr#3. It has also been detected in the sour paste nematode, Panagrellus redivivus.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ZINC000002569973

Download	Molfile XML SDF

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Formula

C15H28O6

Net Charge

Average Mass

304.383

Monoisotopic Mass

304.18859

InChI

InChI=1S/C15H28O6/c1-10(7-5-3-4-6-8-14(18)19)20-15-13(17)9-12(16)11(2)21-15/h10-13,15-17H,3-9H2,1-2H3,(H,18,19)/t10-,11+,12-,13-,15-/m1/s1

InChIKey

MILZHQPVNOSJIP-WPLOAARJSA-N

SMILES

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

Metabolite of Species	Details
Panagrellus redivivus (NCBI:txid6233)	Produced by female P. redivivus. See: PubMed
Caenorhabditis elegans (NCBI:txid6239)	Absent in daf-22(ok693) but is a major ascaroside detected in wild type (N2) and acox-1(ok2257) mutant C. elegans. Detected in dhs-28(hj8) and maoc-1(hj13) mutant C. elegans 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#10 (CHEBI:78838) has functional parent (8R)-8-hydroxynonanoic acid (CHEBI:78839) ascr#10 (CHEBI:78838) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#10 (CHEBI:78838) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#10 (CHEBI:78838) is a monocarboxylic acid (CHEBI:25384) ascr#10 (CHEBI:78838) is conjugate acid of ascr#10(1−) (CHEBI:139615)

Incoming	ascr#10-CoA (CHEBI:139616) has functional parent ascr#10 (CHEBI:78838) bhas#10 (CHEBI:79223) has functional parent ascr#10 (CHEBI:78838) glas#10 (CHEBI:79301) has functional parent ascr#10 (CHEBI:78838) hbas#10 (CHEBI:79330) has functional parent ascr#10 (CHEBI:78838) icas#10 (CHEBI:79029) has functional parent ascr#10 (CHEBI:78838) mbas#10 (CHEBI:79129) has functional parent ascr#10 (CHEBI:78838) ascr#10(1−) (CHEBI:139615) is conjugate base of ascr#10 (CHEBI:78838)

IUPAC Name

(8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]nonanoic acid

Synonyms	Sources
8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acid	SMID
asc-C9	ChEBI

Last Modified

24 January 2024