ascr#7 (CHEBI:78830)

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ChEBI Name	ascr#7

ChEBI ID	CHEBI:78830

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). A metabolite of the nematode Caenorhabditis elegans, it is weakly dauer inducing and a weak male-attractant.

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

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

Formula

C13H22O6

Net Charge

Average Mass

274.31020

Monoisotopic Mass

274.14164

InChI

InChI=1S/C13H22O6/c1-8(5-3-4-6-12(16)17)18-13-11(15)7-10(14)9(2)19-13/h4,6,8-11,13-15H,3,5,7H2,1-2H3,(H,16,17)/b6-4+/t8-,9+,10-,11-,13-/m1/s1

InChIKey

GGHOMCWJOMBZEK-LHYQPRBASA-N

SMILES

C[C@H](CC\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)	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. pheromone A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour. 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#7 (CHEBI:78830) has functional parent (2E,6R)-6-hydroxyhept-2-enoic acid (CHEBI:78831) ascr#7 (CHEBI:78830) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#7 (CHEBI:78830) has role pheromone (CHEBI:26013) ascr#7 (CHEBI:78830) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020) ascr#7 (CHEBI:78830) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205) ascr#7 (CHEBI:78830) is conjugate acid of ascr#7(1-) (CHEBI:139710)

Incoming	ascr#7-CoA (CHEBI:139711) has functional parent ascr#7 (CHEBI:78830) ascr#8 (CHEBI:78834) has functional parent ascr#7 (CHEBI:78830) icas#7 (CHEBI:79023) has functional parent ascr#7 (CHEBI:78830) ascr#7(1-) (CHEBI:139710) is conjugate base of ascr#7 (CHEBI:78830)

IUPAC Name

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

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

Citations

Last Modified

05 January 2021