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CHEBI:78976 - ascr#38

ChEBI IDCHEBI:78976
ChEBI Nameascr#38
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (20R)-20-hydroxyhenicosanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Last Modified25 July 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC27H52O6
Net Charge0
Average Mass472.707
Monoisotopic Mass472.37639
SMILESC[C@H](CCCCCCCCCCCCCCCCCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C27H52O6/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/h22-25,27-29H,3-21H2,1-2H3,(H,30,31)/t22-,23+,24-,25-,27-/m1/s1
InChIKeyNISHIBVYPLRXFI-VYXBAIFMSA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. It is a major ascaroside in daf-22(ok693) 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#38 (CHEBI:78976) has functional parent (20R)-20-hydroxyhenicosanoic acid (CHEBI:79017)
ascr#38 (CHEBI:78976) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#38 (CHEBI:78976) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#38 (CHEBI:78976) is a monocarboxylic acid (CHEBI:25384)
ascr#38 (CHEBI:78976) is conjugate acid of ascr#38(1-) (CHEBI:139702)
Incoming Relation(s)
bhas#38 (CHEBI:79239) has functional parent ascr#38 (CHEBI:78976)
ascr#38(1-) (CHEBI:139702) is conjugate base of ascr#38 (CHEBI:78976)
IUPAC Name 
(20R)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]henicosanoic acid
Synonym  Source
20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-henicosanoic acidSMID
Manual XrefsDatabases
ascr%2338%0DSMID
Registry NumbersSources
Reaxys:22233510Reaxys
CAS:1355681-91-2SMID
Citations