CHEBI:78965 - ascr#27

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ascr#27
ChEBI ID CHEBI:78965
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (2E,15R)-15-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:CB2341505, eMolecules:536524, ZINC000003830515
Download Molfile XML SDF
Formula C22H40O6
Net Charge 0
Average Mass 400.54940
Monoisotopic Mass 400.28249
InChI InChI=1S/C22H40O6/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/h13,15,17-20,22-24H,3-12,14,16H2,1-2H3,(H,25,26)/b15-13+/t17-,18+,19-,20-,22-/m1/s1
InChIKey PHSQDXKUQRUWOG-PXMSNCRXSA-N
SMILES C[C@H](CCCCCCCCCCC\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
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#27 (CHEBI:78965) has functional parent (2E,15R)-15-hydroxyhexadec-2-enoic acid (CHEBI:78997)
ascr#27 (CHEBI:78965) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#27 (CHEBI:78965) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#27 (CHEBI:78965) is conjugate acid of ascr#27(1-) (CHEBI:139668)
Incoming ascr#27(1-) (CHEBI:139668) is conjugate base of ascr#27 (CHEBI:78965)
IUPAC Name
(2E,15R)-15-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexadec-2-enoic acid
Synonym Source
15R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-2E-hexadecenoic acid SMID
Manual Xref Database
ascr%2327%0D SMID
View more database links
Registry Numbers Types Sources
1355681-69-4 CAS Registry Number SMID
22233445 Reaxys Registry Number Reaxys
Citation Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014