CHEBI:78966 - ascr#28

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ascr#28
ChEBI ID CHEBI:78966
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (15R)-15-hydroxypalmitic 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 ChemicalBook:CB6469458, eMolecules:594898, ZINC000016052538
Download Molfile XML SDF
Formula C22H42O6
Net Charge 0
Average Mass 402.56530
Monoisotopic Mass 402.29814
InChI InChI=1S/C22H42O6/c1-17(27-22-20(24)16-19(23)18(2)28-22)14-12-10-8-6-4-3-5-7-9-11-13-15-21(25)26/h17-20,22-24H,3-16H2,1-2H3,(H,25,26)/t17-,18+,19-,20-,22-/m1/s1
InChIKey HSLYPVWJYLQYET-AIYVTKCESA-N
SMILES CC(CCCCCCCCCCCCCC(O)=O)OC1OC(C)C(O)CC1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in dhs-28(hj8), acox-1(ok2257), and maoc-1(hj13) mutant worms and a major ascaroside in daf-22(ok693) 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#28 (CHEBI:78966) has functional parent (15R)-15-hydroxypalmitic acid (CHEBI:78998)
ascr#28 (CHEBI:78966) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#28 (CHEBI:78966) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#28 (CHEBI:78966) is a monocarboxylic acid (CHEBI:25384)
ascr#28 (CHEBI:78966) is conjugate acid of ascr#28(1-) (CHEBI:139671)
Incoming bhas#28 (CHEBI:79234) has functional parent ascr#28 (CHEBI:78966)
ascr#28(1-) (CHEBI:139671) is conjugate base of ascr#28 (CHEBI:78966)
IUPAC Name
(15R)-15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadecanoic acid
Synonym Source
15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexadecanoic acid SMID
Manual Xref Database
ascr%2328%0D SMID
View more database links
Registry Numbers Types Sources
1355681-71-8 CAS Registry Number SMID
22233451 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014