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CHEBI:78841 - ascr#12

ChEBI IDCHEBI:78841
ChEBI Nameascr#12
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (5R)-5-hydroxyhexanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematodes Caenorhabditis elegans and Pristionchus pacificus.
Last Modified24 January 2024
SubmitterGareth Owen
DownloadsMolfile
FormulaC12H22O6
Net Charge0
Average Mass262.302
Monoisotopic Mass262.14164
SMILESC[C@H](CCCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C12H22O6/c1-7(4-3-5-11(15)16)17-12-10(14)6-9(13)8(2)18-12/h7-10,12-14H,3-6H2,1-2H3,(H,15,16)/t7-,8+,9-,10-,12-/m1/s1
InChIKeyLGGOKKRYYYYXPA-VEOFNUSFSA-N
Species of MetaboliteComponentSourceComments
Pristionchus pacificus (ncbitaxon:54126) - PubMed (23161728)
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548) Detected in wild type (N2) and acox-1(ok2257) mutant worms, but absent in daf-22(ok693), 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#12 (CHEBI:78841) has functional parent (5R)-5-hydroxyhexanoic acid (CHEBI:78842)
ascr#12 (CHEBI:78841) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#12 (CHEBI:78841) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#12 (CHEBI:78841) is a monocarboxylic acid (CHEBI:25384)
ascr#12 (CHEBI:78841) is conjugate acid of ascr#12(1−) (CHEBI:139621)
Incoming Relation(s)
icas#12 (CHEBI:79060) has functional parent ascr#12 (CHEBI:78841)
ascr#12(1−) (CHEBI:139621) is conjugate base of ascr#12 (CHEBI:78841)
IUPAC Name 
(5R)-5-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexanoic acid
Synonyms  Source
5R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexanoic acidSMID
asc-C6ChEBI
Manual XrefsDatabases
ascr%2312%0DSMID
LMFA13040038LIPID MAPS
Registry NumbersSources
Reaxys:22233385Reaxys
CAS:1355681-43-4SMID
Citations