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CHEBI:78838 - ascr#10

ChEBI IDCHEBI:78838
ChEBI Nameascr#10
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (8R)-8-hydroxynonanoic acid with ascarylopyranose (the α anomer). A metabolite of the nematode Caenorhabditis elegans, it is the direct biosynthetic precursor to ascr#3. It has also been detected in the sour paste nematode, Panagrellus redivivus.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC15H28O6
Net Charge0
Average Mass304.383
Monoisotopic Mass304.18859
SMILESC[C@H](CCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C15H28O6/c1-10(7-5-3-4-6-8-14(18)19)20-15-13(17)9-12(16)11(2)21-15/h10-13,15-17H,3-9H2,1-2H3,(H,18,19)/t10-,11+,12-,13-,15-/m1/s1
InChIKeyMILZHQPVNOSJIP-WPLOAARJSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Absent in daf-22(ok693) but is a major ascaroside detected in wild type (N2) and acox-1(ok2257) mutant C. elegans. Detected in dhs-28(hj8) and maoc-1(hj13) mutant C. elegans
Panagrellus redivivus (ncbitaxon:6233) - PubMed (23213209) Produced by female P. redivivus.
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
Caenorhabditis elegans metabolite  A nematode metabolite produced by Caenorhabditis elegans.
semiochemical  A molecular messenger released by an organism that affects the behaviour within or between species.
ChEBI Ontology
Outgoing Relation(s)
ascr#10 (CHEBI:78838) has functional parent (8R)-8-hydroxynonanoic acid (CHEBI:78839)
ascr#10 (CHEBI:78838) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#10 (CHEBI:78838) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#10 (CHEBI:78838) is a monocarboxylic acid (CHEBI:25384)
ascr#10 (CHEBI:78838) is conjugate acid of ascr#10(1−) (CHEBI:139615)
Incoming Relation(s)
ascr#10-CoA (CHEBI:139616) has functional parent ascr#10 (CHEBI:78838)
bhas#10 (CHEBI:79223) has functional parent ascr#10 (CHEBI:78838)
glas#10 (CHEBI:79301) has functional parent ascr#10 (CHEBI:78838)
hbas#10 (CHEBI:79330) has functional parent ascr#10 (CHEBI:78838)
icas#10 (CHEBI:79029) has functional parent ascr#10 (CHEBI:78838)
mbas#10 (CHEBI:79129) has functional parent ascr#10 (CHEBI:78838)
ascr#10(1−) (CHEBI:139615) is conjugate base of ascr#10 (CHEBI:78838)
IUPAC Name 
(8R)-8-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]nonanoic acid
Synonyms  Source
8R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-nonanoic acidSMID
asc-C9ChEBI
Manual XrefsDatabases
ascr%2310%0DSMID
LMFA13040008LIPID MAPS
Registry NumbersSources
Reaxys:22233395Reaxys
CAS:1355681-08-1SMID
Citations