ascr#2 (CHEBI:78812)

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ChEBI Name	ascr#2

ChEBI ID	CHEBI:78812

Definition	A hydroxy ketone ascaroside obtained by formal condensation of the hydroxy group of (5R)-5-hydroxyhexan-2-one with ascarylopyranose (the α anomer). It is a major component of the dauer pheromone, used by the nematode Caenorhabditis elegans as a population-density signal to promote entry into an alternate larval stage, the nonfeeding and highly persistent dauer diapause, and also synergises with ascr#3, ascr#4, and ascr#8 in male attraction.

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

Supplier Information	ZINC000034985628

Download	Molfile XML SDF

Formula

C12H22O5

Net Charge

Average Mass

246.30010

Monoisotopic Mass

246.14672

InChI

InChI=1S/C12H22O5/c1-7(13)4-5-8(2)16-12-11(15)6-10(14)9(3)17-12/h8-12,14-15H,4-6H2,1-3H3/t8-,9+,10-,11-,12-/m1/s1

InChIKey

KDIFLHQRDPSWHT-IYKVGLELSA-N

SMILES

C[C@H](CCC(C)=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
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.

ChEBI Ontology
Outgoing	ascr#2 (CHEBI:78812) has functional parent (5R)-5-hydroxyhexan-2-one (CHEBI:78817) ascr#2 (CHEBI:78812) has role Caenorhabditis elegans metabolite (CHEBI:78804) ascr#2 (CHEBI:78812) has role pheromone (CHEBI:26013) ascr#2 (CHEBI:78812) is a hydroxy ketone ascaroside (CHEBI:79201) ascr#2 (CHEBI:78812) is a methyl ketone (CHEBI:51867)

Incoming	ascr#4 (CHEBI:78828) has functional parent ascr#2 (CHEBI:78812)

IUPAC Name

(2R)-5-oxohexan-2-yl 3,6-dideoxy-α-L-arabino-hexopyranoside

Synonyms	Sources
(−)-5R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-hexanone	SMID
ascaroside C6	ChEBI
daumone-2	SMID

Citations

Last Modified

25 July 2014