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CHEBI:78961 - ascr#23

ChEBI IDCHEBI:78961
ChEBI Nameascr#23
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,13R)-13-hydroxytetradec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC20H36O6
Net Charge0
Average Mass372.502
Monoisotopic Mass372.25119
SMILESC[C@H](CCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C20H36O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h11,13,15-18,20-22H,3-10,12,14H2,1-2H3,(H,23,24)/b13-11+/t15-,16+,17-,18-,20-/m1/s1
InChIKeyVZEGHYGOTDETNP-VKEQHCKMSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in 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#23 (CHEBI:78961) has functional parent (2E,13R)-13-hydroxytetradec-2-enoic acid (CHEBI:78982)
ascr#23 (CHEBI:78961) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#23 (CHEBI:78961) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#23 (CHEBI:78961) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#23 (CHEBI:78961) is conjugate acid of ascr#23(1-) (CHEBI:139656)
Incoming Relation(s)
ascr#23(1-) (CHEBI:139656) is conjugate base of ascr#23 (CHEBI:78961)
IUPAC Name 
(2E,13R)-13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tetradec-2-enoic acid
Synonym  Source
13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tetradecenoic acidSMID
Manual XrefsDatabases
ascr%2323%0DSMID
Registry NumbersSources
Reaxys:22233422Reaxys
CAS:1355681-61-6SMID
Citations