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CHEBI:78963 - ascr#25

ChEBI IDCHEBI:78963
ChEBI Nameascr#25
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,14R)-14-hydroxypentadec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC21H38O6
Net Charge0
Average Mass386.529
Monoisotopic Mass386.26684
SMILESC[C@H](CCCCCCCCCC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C21H38O6/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/h12,14,16-19,21-23H,3-11,13,15H2,1-2H3,(H,24,25)/b14-12+/t16-,17+,18-,19-,21-/m1/s1
InChIKeyMTVUVHUAEUQKIN-YWWXTUTHSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in daf-22(ok693) and dhs-28(hj8) mutant worms and a major ascaroside in maoc-1(hj13)
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#25 (CHEBI:78963) has functional parent (2E,14R)-14-hydroxypentadec-2-enoic acid (CHEBI:78991)
ascr#25 (CHEBI:78963) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#25 (CHEBI:78963) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#25 (CHEBI:78963) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#25 (CHEBI:78963) is conjugate acid of ascr#25(1-) (CHEBI:139662)
Incoming Relation(s)
ascr#25(1-) (CHEBI:139662) is conjugate base of ascr#25 (CHEBI:78963)
IUPAC Name 
(2E,14R)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadec-2-enoic acid
Synonym  Source
14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-pentadecenoic acidSMID
Manual XrefsDatabases
ascr%2325%0DSMID
Registry NumbersSources
Reaxys:22233430Reaxys
CAS:1355681-15-0SMID
Citations