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CHEBI:78812 - ascr#2

ChEBI IDCHEBI:78812
ChEBI Nameascr#2
Stars
DefinitionA 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.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC12H22O5
Net Charge0
Average Mass246.303
Monoisotopic Mass246.14672
SMILESCC(=O)CC[C@@H](C)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=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
InChIKeyKDIFLHQRDPSWHT-IYKVGLELSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (17558398)
Roles Classification
Biological Roles:
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
daumone-2SMID
(−)-5R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-hexanoneSMID
ascaroside C6ChEBI
Manual XrefsDatabases
ascr%232%0DSMID
Registry NumbersSources
Reaxys:19924214Reaxys
CAS:946524-24-9SMID
Citations