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CHEBI:78830 - ascr#7

ChEBI IDCHEBI:78830
ChEBI Nameascr#7
Stars
DefinitionAn (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,6R)-6-hydroxyhept-2-enoic acid with ascarylopyranose (the α anomer). A metabolite of the nematode Caenorhabditis elegans, it is weakly dauer inducing and a weak male-attractant.
Last Modified5 January 2021
SubmitterGareth Owen
DownloadsMolfile
FormulaC13H22O6
Net Charge0
Average Mass274.313
Monoisotopic Mass274.14164
SMILESC[C@H](CC/C=C/C(=O)O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
InChIInChI=1S/C13H22O6/c1-8(5-3-4-6-12(16)17)18-13-11(15)7-10(14)9(2)19-13/h4,6,8-11,13-15H,3,5,7H2,1-2H3,(H,16,17)/b6-4+/t8-,9+,10-,11-,13-/m1/s1
InChIKeyGGHOMCWJOMBZEK-LHYQPRBASA-N
Species of MetaboliteComponentSourceComments
Caenorhabditis elegans (ncbitaxon:6239) - PubMed (19346493)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
pheromone  A semiochemical used in olfactory communication between organisms of the same species eliciting a change in sexual or social behaviour.
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#7 (CHEBI:78830) has functional parent (2E,6R)-6-hydroxyhept-2-enoic acid (CHEBI:78831)
ascr#7 (CHEBI:78830) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#7 (CHEBI:78830) has role pheromone (CHEBI:26013)
ascr#7 (CHEBI:78830) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#7 (CHEBI:78830) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#7 (CHEBI:78830) is conjugate acid of ascr#7(1-) (CHEBI:139710)
Incoming Relation(s)
ascr#7-CoA (CHEBI:139711) has functional parent ascr#7 (CHEBI:78830)
ascr#8 (CHEBI:78834) has functional parent ascr#7 (CHEBI:78830)
icas#7 (CHEBI:79023) has functional parent ascr#7 (CHEBI:78830)
ascr#7(1-) (CHEBI:139710) is conjugate base of ascr#7 (CHEBI:78830)
IUPAC Name 
(2E,6R)-6-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hept-2-enoic acid
Synonym  Source
6R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-heptenoic acidSMID
Manual XrefsDatabases
ascr%237%0DSMID
LMFA13040006LIPID MAPS
Registry NumbersSources
Reaxys:22233384Reaxys
CAS:1139837-37-8SMID
Citations