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CHEBI:79018 - ascr#9

ChEBI IDCHEBI:79018
ChEBI Nameascr#9
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (4R)-4-hydroxypentanoic 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
FormulaC11H20O6
Net Charge0
Average Mass248.275
Monoisotopic Mass248.12599
SMILESC[C@H](CCC(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C11H20O6/c1-6(3-4-10(14)15)16-11-9(13)5-8(12)7(2)17-11/h6-9,11-13H,3-5H2,1-2H3,(H,14,15)/t6-,7+,8-,9-,11-/m1/s1
InChIKeyNZMXMOQNHSVRAJ-WNPHYYBUSA-N
Species of MetaboliteComponentSourceComments
Pristionchus pacificus (ncbitaxon:54126) - PubMed (23161728)
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (22239548)
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#9 (CHEBI:79018) has functional parent (4R)-4-hydroxypentanoic acid (CHEBI:79019)
ascr#9 (CHEBI:79018) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#9 (CHEBI:79018) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#9 (CHEBI:79018) is a monocarboxylic acid (CHEBI:25384)
ascr#9 (CHEBI:79018) is conjugate acid of ascr#9(1−) (CHEBI:139714)
Incoming Relation(s)
icas#9 (CHEBI:79028) has functional parent ascr#9 (CHEBI:79018)
ascr#9(1−) (CHEBI:139714) is conjugate base of ascr#9 (CHEBI:79018)
IUPAC Name 
(4R)-4-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentanoic acid
Synonyms  Source
4R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-pentanoic acidSMID
(4R)-4-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]valeric acidChEBI
4R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-valeric acidChEBI
asc-C5ChEBI
Manual XrefsDatabases
ascr%239%0DSMID
LMFA13040007LIPID MAPS
Registry NumbersSources
Reaxys:22233381Reaxys
CAS:1186217-42-4SMID
Citations