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CHEBI:78950 - ascr#16

ChEBI IDCHEBI:78950
ChEBI Nameascr#16
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (9R)-9-hydroxydecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H30O6
Net Charge0
Average Mass318.410
Monoisotopic Mass318.20424
SMILESC[C@H](CCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C16H30O6/c1-11(8-6-4-3-5-7-9-15(19)20)21-16-14(18)10-13(17)12(2)22-16/h11-14,16-18H,3-10H2,1-2H3,(H,19,20)/t11-,12+,13-,14-,16-/m1/s1
InChIKeyUMKVAMCFIAMCAV-JTTNIQEDSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Found in dhs-28(hj8), maoc-1(hj13), 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#16 (CHEBI:78950) has functional parent (9R)-9-hydroxydecanoic acid (CHEBI:78951)
ascr#16 (CHEBI:78950) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#16 (CHEBI:78950) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#16 (CHEBI:78950) is a monocarboxylic acid (CHEBI:25384)
ascr#16 (CHEBI:78950) is conjugate acid of ascr#16(1−) (CHEBI:139633)
Incoming Relation(s)
bhas#16 (CHEBI:79227) has functional parent ascr#16 (CHEBI:78950)
glas#16 (CHEBI:79302) has functional parent ascr#16 (CHEBI:78950)
icas#16 (CHEBI:79094) has functional parent ascr#16 (CHEBI:78950)
ascr#16(1−) (CHEBI:139633) is conjugate base of ascr#16 (CHEBI:78950)
IUPAC Name 
(9R)-9-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]decanoic acid
Synonym  Source
9R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-decanoic acidSMID
Manual XrefsDatabases
ascr%2316%0DSMID
LMFA13040035LIPID MAPS
Registry NumbersSources
Reaxys:22233391Reaxys
CAS:1186217-53-7SMID
Citations