ascr#20 (CHEBI:78958)

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ChEBI Name	ascr#20

ChEBI ID	CHEBI:78958

Definition	An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (11R)-11-hydroxylauric 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

C18H34O6

Net Charge

Average Mass

346.45900

Monoisotopic Mass

346.23554

InChI

InChI=1S/C18H34O6/c1-13(23-18-16(20)12-15(19)14(2)24-18)10-8-6-4-3-5-7-9-11-17(21)22/h13-16,18-20H,3-12H2,1-2H3,(H,21,22)/t13-,14+,15-,16-,18-/m1/s1

InChIKey

SNWMNYQPRXIDAR-ORDFZIBCSA-N

SMILES

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

Metabolite of Species	Details
Caenorhabditis elegans (NCBI:txid6239)	Detected in wild type (N2) and daf-22(ok693), dhs-28(hj8), acox-1(ok2257), and maoc-1(hj13) 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#20 (CHEBI:78958) has functional parent (11R)-11-hydroxylauric acid (CHEBI:78978) ascr#20 (CHEBI:78958) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#20 (CHEBI:78958) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#20 (CHEBI:78958) is a monocarboxylic acid (CHEBI:25384) ascr#20 (CHEBI:78958) is conjugate acid of ascr#20(1-) (CHEBI:139647)

Incoming	bhas#20 (CHEBI:79230) has functional parent ascr#20 (CHEBI:78958) glas#20 (CHEBI:79304) has functional parent ascr#20 (CHEBI:78958) icas#20 (CHEBI:78745) has functional parent ascr#20 (CHEBI:78958) ascr#20(1-) (CHEBI:139647) is conjugate base of ascr#20 (CHEBI:78958)

IUPAC Name

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

Synonyms	Sources
(11R)-11-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]lauric acid	ChEBI
11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-dodecanoic acid	SMID
11R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-lauric acid	ChEBI

Last Modified

25 July 2014