ascr#12 (CHEBI:78841)

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ChEBI Name	ascr#12

ChEBI ID	CHEBI:78841

Definition	An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (5R)-5-hydroxyhexanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematodes Caenorhabditis elegans and Pristionchus pacificus.

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

Supplier Information	ChemicalBook:CB4763080, ChemicalBook:CB8147859, eMolecules:486086, ZINC000059940055

Download	Molfile XML SDF

Formula

C12H22O6

Net Charge

Average Mass

262.29950

Monoisotopic Mass

262.14164

InChI

InChI=1S/C12H22O6/c1-7(4-3-5-11(15)16)17-12-10(14)6-9(13)8(2)18-12/h7-10,12-14H,3-6H2,1-2H3,(H,15,16)/t7-,8+,9-,10-,12-/m1/s1

InChIKey

LGGOKKRYYYYXPA-VEOFNUSFSA-N

SMILES

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

Metabolite of Species	Details
Pristionchus pacificus (NCBI:txid54126)	See: PubMed
Caenorhabditis elegans (NCBI:txid6239)	Detected in wild type (N2) and acox-1(ok2257) mutant worms, but absent in daf-22(ok693), dhs-28(hj8), 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#12 (CHEBI:78841) has functional parent (5R)-5-hydroxyhexanoic acid (CHEBI:78842) ascr#12 (CHEBI:78841) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#12 (CHEBI:78841) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#12 (CHEBI:78841) is a monocarboxylic acid (CHEBI:25384) ascr#12 (CHEBI:78841) is conjugate acid of ascr#12(1−) (CHEBI:139621)

Incoming	icas#12 (CHEBI:79060) has functional parent ascr#12 (CHEBI:78841) ascr#12(1−) (CHEBI:139621) is conjugate base of ascr#12 (CHEBI:78841)

IUPAC Name

(5R)-5-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexanoic acid

Synonyms	Sources
5R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexanoic acid	SMID
asc-C6	ChEBI

Last Modified

24 January 2024