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CHEBI:78952 - ascr#17

ChEBI IDCHEBI:78952
ChEBI Nameascr#17
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,10R)-10-hydroxyundec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H30O6
Net Charge0
Average Mass330.421
Monoisotopic Mass330.20424
SMILESC[C@H](CCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C17H30O6/c1-12(9-7-5-3-4-6-8-10-16(20)21)22-17-15(19)11-14(18)13(2)23-17/h8,10,12-15,17-19H,3-7,9,11H2,1-2H3,(H,20,21)/b10-8+/t12-,13+,14-,15-,17-/m1/s1
InChIKeyNEVPBIQTDNVVMK-KUTOLYOMSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and dhs-28(hj8) and 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#17 (CHEBI:78952) has functional parent (2E,10R)-10-hydroxyundec-2-enoic acid (CHEBI:78953)
ascr#17 (CHEBI:78952) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#17 (CHEBI:78952) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#17 (CHEBI:78952) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#17 (CHEBI:78952) is conjugate acid of ascr#17(1-) (CHEBI:139636)
Incoming Relation(s)
icas#17 (CHEBI:79104) has functional parent ascr#17 (CHEBI:78952)
ascr#17(1-) (CHEBI:139636) is conjugate base of ascr#17 (CHEBI:78952)
IUPAC Name 
(2E,10R)-10-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]undec-2-enoic acid
Synonym  Source
10R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-undecenoic acidSMID
Manual XrefsDatabases
ascr%2317%0DSMID
Registry NumbersSources
Reaxys:22233405Reaxys
CAS:1186217-53-7SMID
Citations