CHEBI:78841 - ascr#12

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ChEBI Name ascr#12
ChEBI ID CHEBI:78841
Definition An (ω−1)-hydroxy fatty acid ascaroside obtained by formal condensation of the alcoholic hydroxy group of (5R)-5-hydroxyhexanoic acid with ascarylopyranose (the α anomer). It is a metabolite of the nematodes Caenorhabditis elegans and Pristionchus pacificus.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C12H22O6
Net Charge 0
Average Mass 262.29950
Monoisotopic Mass 262.14164
InChI InChI=1S/C12H22O6/c1-7(4-3-5-11(15)16)17-12-10(14)6-9(13)8(2)18-12/h7-10,12-14H,3-6H2,1-2H3,(H,15,16)/t7-,8+,9-,10-,12-/m1/s1
InChIKey LGGOKKRYYYYXPA-VEOFNUSFSA-N
SMILES C[C@H](CCCC(O)=O)O[C@@H]1O[C@@H](C)[C@H](O)C[C@H]1O
Metabolite of Species Details
Pristionchus pacificus (NCBI:txid54126) See: PubMed
Caenorhabditis elegans (NCBI:txid6239) Detected in wild type (N2) and acox-1(ok2257) mutant worms, but absent in daf-22(ok693), dhs-28(hj8), and maoc-1(hj13) 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#12 (CHEBI:78841) has functional parent (5R)-5-hydroxyhexanoic acid (CHEBI:78842)
ascr#12 (CHEBI:78841) has role Caenorhabditis elegans metabolite (CHEBI:78804)
ascr#12 (CHEBI:78841) is a (ω−1)-hydroxy fatty acid ascaroside (CHEBI:79205)
ascr#12 (CHEBI:78841) is a monocarboxylic acid (CHEBI:25384)
ascr#12 (CHEBI:78841) is conjugate acid of ascr#12(1−) (CHEBI:139621)
Incoming icas#12 (CHEBI:79060) has functional parent ascr#12 (CHEBI:78841)
ascr#12(1−) (CHEBI:139621) is conjugate base of ascr#12 (CHEBI:78841)
IUPAC Name
(5R)-5-[(3,6-dideoxy-α-L-arabino-hexopyranosyl)oxy]hexanoic acid
Synonyms Sources
5R-(3'R,5'R-dihydroxy-6'S-methyl-(2H)-tetrahydropyran-2'-yloxy)-hexanoic acid SMID
asc-C6 ChEBI
Manual Xrefs Databases
ascr%2312%0D SMID
LMFA13040038 LIPID MAPS
View more database links
Registry Numbers Types Sources
1355681-43-4 CAS Registry Number SMID
22233385 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
22239548 PubMed citation Europe PMC
22503501 PubMed citation Europe PMC
23161728 PubMed citation Europe PMC
23213209 PubMed citation Europe PMC
29863473 PubMed citation Europe PMC
Last Modified
24 January 2024