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CHEBI:78975 - ascr#37

ChEBI IDCHEBI:78975
ChEBI Nameascr#37
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,20R)-20-hydroxyhenicos-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H50O6
Net Charge0
Average Mass470.691
Monoisotopic Mass470.36074
SMILESC[C@H](CCCCCCCCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C27H50O6/c1-22(32-27-25(29)21-24(28)23(2)33-27)19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-26(30)31/h18,20,22-25,27-29H,3-17,19,21H2,1-2H3,(H,30,31)/b20-18+/t22-,23+,24-,25-,27-/m1/s1
InChIKeyIRXQRQDBIJEMEI-OQERHXAMSA-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#37 (CHEBI:78975) has functional parent (2E,20R)-20-hydroxyhenicos-2-enoic acid (CHEBI:79016)
ascr#37 (CHEBI:78975) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#37 (CHEBI:78975) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#37 (CHEBI:78975) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#37 (CHEBI:78975) is conjugate acid of ascr#37(1-) (CHEBI:139699)
Incoming Relation(s)
ascr#37(1-) (CHEBI:139699) is conjugate base of ascr#37 (CHEBI:78975)
IUPAC Name 
(2E,20R)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]henicos-2-enoic acid
Synonym  Source
20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-henicosenoic acidSMID
Manual XrefsDatabases
ascr%2337%0DSMID
Registry NumbersSources
Reaxys:22233509Reaxys
CAS:1355681-89-8SMID
Citations