CHEBI:78976 - ascr#38

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name ascr#38
ChEBI ID CHEBI:78976
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (20R)-20-hydroxyhenicosanoic 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 C27H52O6
Net Charge 0
Average Mass 472.69820
Monoisotopic Mass 472.37639
InChI InChI=1S/C27H52O6/c1-22(32-27-25(29)21-24(28)23(2)33-27)19-17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20-26(30)31/h22-25,27-29H,3-21H2,1-2H3,(H,30,31)/t22-,23+,24-,25-,27-/m1/s1
InChIKey NISHIBVYPLRXFI-VYXBAIFMSA-N
SMILES C[C@H](CCCCCCCCCCCCCCCCCCC(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. It is 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#38 (CHEBI:78976) has functional parent (20R)-20-hydroxyhenicosanoic acid (CHEBI:79017)
ascr#38 (CHEBI:78976) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#38 (CHEBI:78976) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#38 (CHEBI:78976) is a monocarboxylic acid (CHEBI:25384)
ascr#38 (CHEBI:78976) is conjugate acid of ascr#38(1-) (CHEBI:139702)
Incoming bhas#38 (CHEBI:79239) has functional parent ascr#38 (CHEBI:78976)
ascr#38(1-) (CHEBI:139702) is conjugate base of ascr#38 (CHEBI:78976)
IUPAC Name
(20R)-20-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]henicosanoic acid
Synonym Source
20R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-henicosanoic acid SMID
Manual Xref Database
ascr%2338%0D SMID
View more database links
Registry Numbers Types Sources
1355681-91-2 CAS Registry Number SMID
22233510 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
22239548 PubMed citation Europe PMC
Last Modified
25 July 2014