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CHEBI:78905 - ascr#14

ChEBI IDCHEBI:78905
ChEBI Nameascr#14
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (7R)-7-hydroxyoctanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC14H26O6
Net Charge0
Average Mass290.356
Monoisotopic Mass290.17294
SMILESC[C@H](CCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C14H26O6/c1-9(6-4-3-5-7-13(17)18)19-14-12(16)8-11(15)10(2)20-14/h9-12,14-16H,3-8H2,1-2H3,(H,17,18)/t9-,10+,11-,12-,14-/m1/s1
InChIKeyHRHMWTOQBKRTTG-CYRBOEJBSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms and acox-1(ok2257) mutant worms.
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#14 (CHEBI:78905) has functional parent (7R)-7-hydroxyoctanoic acid (CHEBI:78949)
ascr#14 (CHEBI:78905) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#14 (CHEBI:78905) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#14 (CHEBI:78905) is a monocarboxylic acid (CHEBI:25384)
ascr#14 (CHEBI:78905) is conjugate acid of ascr#14(1−) (CHEBI:139627)
Incoming Relation(s)
icas#14 (CHEBI:79061) has functional parent ascr#14 (CHEBI:78905)
ascr#14(1−) (CHEBI:139627) is conjugate base of ascr#14 (CHEBI:78905)
IUPAC Name 
(7R)-7-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]octanoic acid
Synonyms  Source
7R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-octanoic acidSMID
asc-C8ChEBI
Manual XrefsDatabases
ascr%2314%0DSMID
LMFA13040036LIPID MAPS
Registry NumbersSources
Reaxys:22233391Reaxys
CAS:1355681-47-8SMID
Citations