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CHEBI:78852 - ascr#15

ChEBI IDCHEBI:78852
ChEBI Nameascr#15
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,9R)-9-hydroxydec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified24 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H28O6
Net Charge0
Average Mass316.394
Monoisotopic Mass316.18859
SMILESC[C@H](CCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C16H28O6/c1-11(8-6-4-3-5-7-9-15(19)20)21-16-14(18)10-13(17)12(2)22-16/h7,9,11-14,16-18H,3-6,8,10H2,1-2H3,(H,19,20)/b9-7+/t11-,12+,13-,14-,16-/m1/s1
InChIKeyMZJGOAYSXTVLMG-NSKGPKHTSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in maoc-1(hj13) 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#15 (CHEBI:78852) has functional parent (2E,9R)-9-hydroxydec-2-enoic acid (CHEBI:78853)
ascr#15 (CHEBI:78852) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#15 (CHEBI:78852) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#15 (CHEBI:78852) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#15 (CHEBI:78852) is conjugate acid of ascr#15(1-) (CHEBI:139630)
Incoming Relation(s)
icas#15 (CHEBI:79062) has functional parent ascr#15 (CHEBI:78852)
ascr#15(1-) (CHEBI:139630) is conjugate base of ascr#15 (CHEBI:78852)
IUPAC Name 
(2E,9R)-9-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]dec-2-enoic acid
Synonym  Source
9R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-decenoic acidSMID
Manual XrefsDatabases
ascr%2315%0DSMID
Registry NumbersSources
Reaxys:22233399Reaxys
CAS:1355681-49-0SMID
Citations