CHEBI:78961 - ascr#23

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ChEBI Name ascr#23
ChEBI ID CHEBI:78961
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,13R)-13-hydroxytetradec-2-enoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematode Caenorhabditis elegans.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H36O6
Net Charge 0
Average Mass 372.49620
Monoisotopic Mass 372.25119
InChI InChI=1S/C20H36O6/c1-15(25-20-18(22)14-17(21)16(2)26-20)12-10-8-6-4-3-5-7-9-11-13-19(23)24/h11,13,15-18,20-22H,3-10,12,14H2,1-2H3,(H,23,24)/b13-11+/t15-,16+,17-,18-,20-/m1/s1
InChIKey VZEGHYGOTDETNP-VKEQHCKMSA-N
SMILES C[C@H](CCCCCCCCC\C=C\C(O)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in dhs-28(hj8) and maoc-1(hj13) mutant worms. See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
(via hydroxy fatty acid ascaroside )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing ascr#23 (CHEBI:78961) has functional parent (2E,13R)-13-hydroxytetradec-2-enoic acid (CHEBI:78982)
ascr#23 (CHEBI:78961) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#23 (CHEBI:78961) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#23 (CHEBI:78961) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#23 (CHEBI:78961) is conjugate acid of ascr#23(1-) (CHEBI:139656)
Incoming ascr#23(1-) (CHEBI:139656) is conjugate base of ascr#23 (CHEBI:78961)
IUPAC Name
(2E,13R)-13-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]tetradec-2-enoic acid
Synonym Source
13R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-tetradecenoic acid SMID
Manual Xref Database
ascr%2323%0D SMID
View more database links
Registry Numbers Types Sources
1355681-61-6 CAS Registry Number SMID
22233422 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
19174521 PubMed citation Europe PMC
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014