CHEBI:78963 - ascr#25

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ChEBI Name ascr#25
ChEBI ID CHEBI:78963
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,14R)-14-hydroxypentadec-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 ZINC000219950655
Download Molfile XML SDF
Formula C21H38O6
Net Charge 0
Average Mass 386.52280
Monoisotopic Mass 386.26684
InChI InChI=1S/C21H38O6/c1-16(26-21-19(23)15-18(22)17(2)27-21)13-11-9-7-5-3-4-6-8-10-12-14-20(24)25/h12,14,16-19,21-23H,3-11,13,15H2,1-2H3,(H,24,25)/b14-12+/t16-,17+,18-,19-,21-/m1/s1
InChIKey MTVUVHUAEUQKIN-YWWXTUTHSA-N
SMILES C[C@H](CCCCCCCCCC\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 daf-22(ok693) and dhs-28(hj8) mutant worms and a major ascaroside in maoc-1(hj13) 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#25 (CHEBI:78963) has functional parent (2E,14R)-14-hydroxypentadec-2-enoic acid (CHEBI:78991)
ascr#25 (CHEBI:78963) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#25 (CHEBI:78963) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
ascr#25 (CHEBI:78963) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#25 (CHEBI:78963) is conjugate acid of ascr#25(1-) (CHEBI:139662)
Incoming ascr#25(1-) (CHEBI:139662) is conjugate base of ascr#25 (CHEBI:78963)
IUPAC Name
(2E,14R)-14-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]pentadec-2-enoic acid
Synonym Source
14R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-pentadecenoic acid SMID
Manual Xref Database
ascr%2325%0D SMID
View more database links
Registry Numbers Types Sources
1355681-15-0 CAS Registry Number SMID
22233430 Reaxys Registry Number Reaxys
Citations Waiting for Citations
Last Modified
25 July 2014