CHEBI:78828 - ascr#4

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ChEBI Name ascr#4
ChEBI ID CHEBI:78828
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C18H32O10
Net Charge 0
Average Mass 408.44070
Monoisotopic Mass 408.19955
InChI InChI=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
InChIKey HFJWZOCWIUZTNY-WLJKUCSMSA-N
SMILES C[C@H](CCC(C)=O)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
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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-hexanone SMID
Manual Xref Database
ascr%234 SMID
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Registry Numbers Types Sources
1255514-32-9 CAS Registry Number SMID
23084288 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18650807 PubMed citation Europe PMC
19346493 PubMed citation Europe PMC
19496754 PubMed citation Europe PMC
19649780 PubMed citation Europe PMC
19665885 PubMed citation Europe PMC
20135027 PubMed citation Europe PMC
20151418 PubMed citation Europe PMC
21423575 PubMed citation Europe PMC
21959166 PubMed citation Europe PMC
22239548 PubMed citation Europe PMC
22665789 PubMed citation Europe PMC
22701701 PubMed citation Europe PMC
Last Modified
25 July 2014