EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:78964 - ascr#26

ChEBI IDCHEBI:78964
ChEBI Nameascr#26
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (14R)-14-hydroxypentadecanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H40O6
Net Charge0
Average Mass388.545
Monoisotopic Mass388.28249
SMILESC[C@H](CCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C21H40O6/c1-16(26-21-19(23)15-18(22)17(2)27-21)13-11-9-7-5-3-4-6-8-10-12-14-20(24)25/h16-19,21-23H,3-15H2,1-2H3,(H,24,25)/t16-,17+,18-,19-,21-/m1/s1
InChIKeyGOMRKSMHAWREDI-TWHPPBISSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and daf-22(ok693), dhs-28(hj8), acox-1(ok2257), 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#26 (CHEBI:78964) has functional parent (14R)-14-hydroxypentadecanoic acid (CHEBI:78996)
ascr#26 (CHEBI:78964) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#26 (CHEBI:78964) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#26 (CHEBI:78964) is a monocarboxylic acid (CHEBI:25384)
ascr#26 (CHEBI:78964) is conjugate acid of ascr#26(1-) (CHEBI:139665)
Incoming Relation(s)
bhas#26 (CHEBI:79233) has functional parent ascr#26 (CHEBI:78964)
glas#26 (CHEBI:79307) has functional parent ascr#26 (CHEBI:78964)
ascr#26(1-) (CHEBI:139665) is conjugate base of ascr#26 (CHEBI:78964)
IUPAC Name 
(14R)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadecanoic acid
Synonym  Source
14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentadecanoic acidSMID
Manual XrefsDatabases
ascr%2326%0DSMID
Registry NumbersSources
Reaxys:22233437Reaxys
CAS:1355681-67-2SMID
Citations