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CHEBI:78965 - ascr#27

ChEBI IDCHEBI:78965
ChEBI Nameascr#27
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,15R)-15-hydroxyhexadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC22H40O6
Net Charge0
Average Mass400.556
Monoisotopic Mass400.28249
SMILESC[C@H](CCCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C22H40O6/c1-17(27-22-20(24)16-19(23)18(2)28-22)14-12-10-8-6-4-3-5-7-9-11-13-15-21(25)26/h13,15,17-20,22-24H,3-12,14,16H2,1-2H3,(H,25,26)/b15-13+/t17-,18+,19-,20-,22-/m1/s1
InChIKeyPHSQDXKUQRUWOG-PXMSNCRXSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (222395484) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms.
Roles Classification
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#27 (CHEBI:78965) has functional parent (2E,15R)-15-hydroxyhexadec-2-enoic acid (CHEBI:78997)
ascr#27 (CHEBI:78965) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#27 (CHEBI:78965) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#27 (CHEBI:78965) is conjugate acid of ascr#27(1-) (CHEBI:139668)
Incoming Relation(s)
ascr#27(1-) (CHEBI:139668) is conjugate base of ascr#27 (CHEBI:78965)
IUPAC Name 
(2E,15R)-15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadec-2-enoic acid
Synonym  Source
15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-hexadecenoic acidSMID
Manual XrefsDatabases
ascr%2327%0DSMID
Registry NumbersSources
Reaxys:22233445Reaxys
CAS:1355681-69-4SMID
Citations