EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:78828 - ascr#4

ChEBI IDCHEBI:78828
ChEBI Nameascr#4
Stars
DefinitionA hydroxy ketone ascaroside that is ascr#2 in which the hydroxy group at position 2 of the ascarylopyranose moiety has been converted to the corresponding β-D-glucoside. A metabolite of the nematode Caenorhabditis elegans, it is only weakly dauer inducing, but synergises with ascr#2, ascr#3, and ascr#8 in male attraction.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC18H32O10
Net Charge0
Average Mass408.444
Monoisotopic Mass408.19955
SMILESCC(=O)CC[C@@H](C)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIInChI=1S/C18H32O10/c1-8(20)4-5-9(2)25-17-12(6-11(21)10(3)26-17)27-18-16(24)15(23)14(22)13(7-19)28-18/h9-19,21-24H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14-,15+,16-,17-,18-/m1/s1
InChIKeyHFJWZOCWIUZTNY-WLJKUCSMSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (18650807)
Roles Classification
Biological Roles:
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 Relation(s)
ascr#4 (CHEBI:78828) has functional parent ascr#2 (CHEBI:78812)
ascr#4 (CHEBI:78828) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#4 (CHEBI:78828) has role pheromone (CHEBI:26013)
ascr#4 (CHEBI:78828) is a glycosyl glycoside derivative (CHEBI:63356)
ascr#4 (CHEBI:78828) is a hydroxy ketone ascaroside (CHEBI:79201)
ascr#4 (CHEBI:78828) is a methyl ketone (CHEBI:51867)
IUPAC Name 
(2R)-5-oxohexan-2-yl 3,6-dideoxy-2-O-β-D-glucopyranosyl-α-L-arabino-hexopyranoside
Synonym  Source
(−)-5R-(3'-O-[β-D-glucosyl]-3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2-hexanoneSMID
Manual XrefsDatabases
ascr%234SMID
Registry NumbersSources
Reaxys:23084288Reaxys
CAS:1255514-32-9SMID
Citations