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CHEBI:79133 - oscr#9

ChEBI IDCHEBI:79133
ChEBI Nameoscr#9
Stars
DefinitionAn ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of 5-hydroxypentanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified19 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC11H20O6
Net Charge0
Average Mass248.275
Monoisotopic Mass248.12599
SMILESC[C@@H]1O[C@@H](OCCCCC(=O)O)[C@H](O)C[C@H]1O
InChIInChI=1S/C11H20O6/c1-7-8(12)6-9(13)11(17-7)16-5-3-2-4-10(14)15/h7-9,11-13H,2-6H2,1H3,(H,14,15)/t7-,8+,9+,11+/m0/s1
InChIKeyRGLRYSHQCRBEIV-YSSBGUOXSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) worms and is a major ascaroside in 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)
oscr#9 (CHEBI:79133) has functional parent 5-hydroxypentanoic acid (CHEBI:45564)
oscr#9 (CHEBI:79133) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#9 (CHEBI:79133) is a monocarboxylic acid (CHEBI:25384)
oscr#9 (CHEBI:79133) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#9 (CHEBI:79133) is conjugate acid of oscr#9(1−) (CHEBI:140058)
Incoming Relation(s)
icos#9 (CHEBI:79116) has functional parent oscr#9 (CHEBI:79133)
oscr#9-CoA (CHEBI:140059) has functional parent oscr#9 (CHEBI:79133)
oscr#9(1−) (CHEBI:140058) is conjugate base of oscr#9 (CHEBI:79133)
IUPAC Name 
5-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentanoic acid
Synonym  Source
5-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acidSMID
Manual XrefsDatabases
oscr%239SMID
Registry NumbersSources
Reaxys:22233383Reaxys
CAS:1355681-20-7SMID
Citations