CHEBI:79149 - oscr#27

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name oscr#27
ChEBI ID CHEBI:79149
Definition An ω-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E)-16-hydroxyhexadec-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 ChemicalBook:CB51270100, ChemicalBook:CB4210362, ZINC000004468778
Download Molfile XML SDF
Formula C22H40O6
Net Charge 0
Average Mass 400.54940
Monoisotopic Mass 400.28249
InChI InChI=1S/C22H40O6/c1-18-19(23)17-20(24)22(28-18)27-16-14-12-10-8-6-4-2-3-5-7-9-11-13-15-21(25)26/h13,15,18-20,22-24H,2-12,14,16-17H2,1H3,(H,25,26)/b15-13+/t18-,19+,20+,22+/m0/s1
InChIKey BEKLYIAFACFFDO-UPBMBJRSSA-N
SMILES C[C@@H]1O[C@@H](OCCCCCCCCCCCCC\C=C\C(O)=O)[C@H](O)C[C@H]1O
Metabolite of Species Details
Caenorhabditis elegans (NCBI:txid6239) Detected in maoc-1(hj13), and dhs-28(hj8) 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 oscr#27 (CHEBI:79149) has functional parent (2E)-16-hydroxyhexadec-2-enoic acid (CHEBI:79170)
oscr#27 (CHEBI:79149) has role Caenorhabditis elegans metabolite (CHEBI:78804)
oscr#27 (CHEBI:79149) is a α,β-unsaturated monocarboxylic acid (CHEBI:79020)
oscr#27 (CHEBI:79149) is a ω-hydroxy fatty acid ascaroside (CHEBI:79204)
oscr#27 (CHEBI:79149) is conjugate acid of oscr#27(1−) (CHEBI:140016)
Incoming oscr#27-CoA (CHEBI:140017) has functional parent oscr#27 (CHEBI:79149)
oscr#27(1−) (CHEBI:140016) is conjugate base of oscr#27 (CHEBI:79149)
IUPAC Name
(2E)-16-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadec-2-enoic acid
Synonym Source
16-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-hexadecenoic acid SMID
Manual Xref Database
oscr%2327 SMID
View more database links
Registry Numbers Types Sources
1355682-27-7 CAS Registry Number SMID
22233447 Reaxys Registry Number Reaxys
Citation Type Source
22239548 PubMed citation Europe PMC
Last Modified
23 February 2018